Frank Sinatra

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Frank Sinatra
Frank Sinatra '57.jpg
Sinatra in 1957

Francis Albert "Frank" Sinatra (/sɨˈnɑːtrə/; December 12, 1915 – May 14, 1998) was an American singer, actor, director, and film producer. Beginning his musical career in the swing era as a boy singer with Harry James and Tommy Dorsey, Sinatra found success as a solo artist from the early to mid-1940s after being signed by Columbia Records in 1943. The idol of the "bobby soxers", he released his first album, The Voice of Frank Sinatra, in 1946. His professional career had stalled by the early 1950s, but it was reborn in 1953 after he won the Academy Award for Best Supporting Actor for his performance in From Here to Eternity. He signed with Capitol Records in 1953 and released several critically lauded albums (such as In the Wee Small Hours, Songs for Swingin' Lovers!, Come Fly with Me, Only the Lonely and Nice 'n' Easy). Sinatra left Capitol to start his own record label, Reprise Records, in 1961, finding success with albums such as Ring-a-Ding-Ding!, Sinatra at the Sands and Francis Albert Sinatra & Antonio Carlos Jobim. He toured internationally, was a founding member of the Rat Pack and fraternized with celebrities and statesmen, including John F. Kennedy.

In 1965, Sinatra recorded the retrospective September of My Years, starred in the Emmy-winning television special Frank Sinatra: A Man and His Music, and scored hits with "Strangers in the Night" and "My Way". In 1967, he recorded one of his most famous collaborations with Tom Jobim, the album Francis Albert Sinatra & Antonio Carlos Jobim, which was nominated for the Grammy Award for Album of the Year. It was followed by 1968's collaboration with Duke Ellington. With sales of his music dwindling and after appearing in several poorly received films, Sinatra retired for the first time in 1971. Two years later, however, he came out of retirement and from 1973 recorded several albums, scoring a Top 40 hit with "(Theme From) New York, New York" in 1980. Using his Las Vegas shows as a home base, he toured both within the United States and internationally until a short time before his death in 1998.

Sinatra also forged a highly successful career as a film actor. After winning the Academy Award for Best Supporting Actor in 1953, he also garnered a nomination for Best Actor for The Man with the Golden Arm (1955), and critical acclaim for his performance in The Manchurian Candidate (1962). He also starred in such musicals as On the Town (1949), Guys and Dolls (1955), High Society (1956), and Pal Joey (1957).

Sinatra is one of the best-selling music artists of all time, having sold more than 150 million records worldwide.[3] He was honored at the Kennedy Center Honors in 1983, was awarded the Presidential Medal of Freedom by Ronald Reagan in 1985, and the Congressional Gold Medal in 1997. Sinatra was also the recipient of eleven Grammy Awards, including the Grammy Trustees Award, Grammy Legend Award and the Grammy Lifetime Achievement Award. One of the most popular and influential musical artists of the 20th century, Sinatra's popularity was later matched only by Elvis Presley, the Beatles,[4] and Michael Jackson.[5] American music critic Robert Christgau called him "the greatest singer of the 20th century".[6]

Early life[edit]

Family background and early years[edit]

Hoboken, New Jersey in the early 20th century

Francis Albert Sinatra was born on December 12, 1915, in an upstairs tenement at Monroe Street in Hoboken, New Jersey, the only child of Italian immigrants Natalina "Dolly" Garaventa and Antonino Martino "Marty" Sinatra.[7][8] The couple had married on February 14, 1914, in a civil ceremony in Jersey City, New Jersey.[9]

At birth Sinatra weighed 13.5 pounds (6.1 kg)[10] and had to be delivered with the aid of forceps, which caused severe scarring to his left cheek, neck, and ear, and perforated his ear drum, damage which remained for life.[11][12] A childhood operation on his mastoid bone left major scarring on his neck, and during adolescence he suffered from cystic acne that scarred his face and neck.[13] Some children called him "Scarface" when he was eleven, which made him so angry he located the home of the doctor who had delivered him so he could assault the man, who wasn't home at the time[14] Sinatra was raised Roman Catholic,[15][16] but due to his injuries at birth, his baptism was delayed for several months.[10]

His mother, Dolly, an "extrovert blonde" barely five feet tall,[17][11] was the daughter of a lithographer.[18] She was born in Genoa in northern Italy, and was brought to the United States when she was two month old.[19] Sinatra's father, a small, blue-eyed, ruddy-complexioned man,[19] came from Catania in Sicily.[7] He was a bantamweight boxer who fought under the name Marty O'Brien,[7] but retiring from boxing in 1926 after having broken both wrists. He found work on the docks as a boilermaker, but was soon laid off due to problems with asthma.[20] He later served with the Hoboken Fire Department for 24 years, working his way up to Captain.[21] Dolly was influential in the neighborhood and in local Democratic Party circles.[22] She became a ward committee leader,[23] the first immigrant woman to hold that position in her local third ward, and reliably delivered up to 600 votes for Democratic candidates.[24] According to Sinatra biographer Kitty Kelley, Dolly was a foul-mouthed woman of "such gall that men had to recognize her as their equal".[25] She had legitimate employment as an Italian-English interpreter for the local court,[26] and as a midwife,[23] but Kelley claims Dolly also ran an illegal abortion operation that provided services to Italian Catholic girls, given that pregnancy out of wedlock at the time would lead to their family disowning them. Kelly stated that Dolly was so well known for her services that doctors referred their patients to her, and she would travel as far afield as Jersey City and Union City.[27][a]

When Sinatra was a small child, Prohibition came into effect, and in those years Dolly and Marty ran a tavern, allowed to operate openly by local officials, who refused to enforce Prohibition laws.[25] When Sinatra was six, his uncle Babe, Dolly's brother, was arrested for driving a getaway car after a Railway Express truck driver was murdered. Though Dolly attended his trial daily and attempted to evoke sympathy, her brother was convicted and sentenced to prison for 15 years.[17] Other family members had minor clashes with the law; Sinatra's father and uncles had been arrested for assorted minor offenses.[32]

During the Great Depression, Dolly provided money to her son for outings with friends, and for him to buy expensive clothes.[33] He also earned pocket money as a little boy singing on street corners.[34] Neighbors described Sinatra as the "best-dressed kid in the neighborhood" and the "richest kid on the block", aided by the fact that he was an only child, and had his own bedroom.[35] Although Dolly doted on her son, she had very high expectations for him and punished him when he didn't meet them.[36] Excessively thin and small as a child and young man, Sinatra's skinny frame later became a staple of his own jokes and those of the Rat Pack members during stage shows, one self-effacing joke being "A little kid, skinny. So skinny my eyes were single file. Between those two and my belly button my old man thought I was a clarinet".[37]

Education and musical development[edit]

Sinatra developed an interest in music, particularly big band jazz, from a young age, and became addicted to listening to the radio, "entranced by the new musical and comedy routines and captivated by the huge audiences they commanded", according to biographer Chris Rojek.[38] He began singing at a young age, sitting on top of the piano at his parent's bar in Hoboken, "Marty's O'Brien's.[39] Dolly was not enthusiastic at the idea of her son becoming a singer, but she realized when Sinatra was as young as 11 he had something. Sinatra later recalled: "One day, I got a nickel. I said "This is the racket". I thought, "It's wonderful to sing.... I never forgot it." During his early teenage years Sinatra forced himself to develop his voice. wanting to "make something of himself". He listened heavily to Gene Austin, Rudy Vallée, Russ Colombo and Bob Eberly, and "idolized" Bing Crosby, adopting Crosby's props such as a sailor's cap and pipe in his own performances.[40] Sinatra's maternal uncle, Domenico, gave him a ukulele for his 15th birthday, and he began performing at family gatherings.[41]

Sinatra graduated from David E. Rue Junior High,[42] and enrolled at A. J. Demarest High School on January 28, 1931, where he arranged bands for school dances.[41] He left without graduating, having attended only 47 days before being expelled for "general rowdiness".[38][42] The school principal, Arthur Stover stated that he "showed no real talent for anything", while Macy Hagerty, his Maths teacher, described him as a "lazy boy" with "absolutely no ambition at all when it came to school".[43] Sinatra's father was particularly disappointed with his son, hoping that he would make it to college. Sinatra recalled his father scolding him in his strong local accent on the school step after Stover ordered Sinatra senior to "get him out", exclaiming, "What's the matter with you? You don't want to learn nothing?"[37] To please his mother, he enrolled at Drake Business School, but departed after 11 months.[41]

First jobs[edit]

Sinatra's father, who knew that his son was interested in getting into show business, insisted that his son find a "real job" to avoid becoming a "bum" after leaving school.[37] Dolly found him work as a delivery boy at the Jersey Observer newspaper, where his godfather Frank Garrick worked,[b] and briefly as a riveter at the Tietjen and Lang shipyard.[45] She was also responsible for his job at the Union Club at 600 Hudson Street in Hoboken, run by Joseph Samperi, where he was paid $40 a week for five weeks.[46] He performed in local Hoboken social clubs such as The Cat's Meow and The Comedy Club, and sang for free on radio stations such as WAAT in Jersey City.[47] In New York he found jobs singing for his supper or for cigarettes.[41] Sinatra began taking 45-minute elocution lessons for a dollar an hour under New York-based vocal coach John Quinlan to improve his speech. Quinlan was impressed by his vocal range, remarking, "He has far more voice that people think he has. He can vocalize to a B-flat on top in full voice, and he doesn't need a mike either". Years later, Sinatra professed that he had never had a proper vocal lesson, but that Quinlan had simply helped him work on vocal calisthenics to "help the throat grow and add a couple of notes on the top and spread the bottom".[48]

In 1938, Sinatra found employment as a singing waiter at a roadhouse called The Rustic Cabin in Englewood Cliffs, New Jersey, for which he was paid $15 a week. The roadhouse was connected to the WNEW radio station in New York City, and Sinatra began performing with a group live during the Dance Parade show.[49][50] Despite the low salary, he felt that this was the break he was looking for, and boasted to friends that he was going to "become so big that no one could ever touch him".[51] Fellow musicians began to resent his cocksure attitude, and according to one Jersey city musician, Sam Lefaso, Sinatra was mocked for displaying little talent and having a "tight, high voice", which sounded "awful". When they told him that he was a lousy singer, Sinatra would flare up, angrily cursing and swearing at the others.[52] It was while working at The Cabin that he became involved in a dispute between his girlfriend Toni Della Penta, who suffered a miscarriage, and Nancy Barbato, a stonemason's daughter, in 1939.[17] Sinatra had met Barbato in Long Branch, New Jersey, where he spent most of the summer working as a lifeguard.[53] After Della Penta attempted to tear off Barbato's dress, Sinatra ordered Barbato away and told Della Pinta that he would marry Barbato, several years his junior, because she was pregnant. Della Penta went to the police, and Sinatra was arrested on a morals charge for seduction. After a fight between Della Penta and Dolly, Della Penta was later arrested herself.[17] Sinatra married Barbato that year,[54] and Nancy Sinatra was born the following year.[55]

Musical career[edit]

The Hoboken Four and Harry James (1935–39)[edit]

Sinatra (far right) with the Hoboken Four on Major Bowes' Amateur Hour

Sinatra began singing professionally as a teenager in the 1930s, although he learned music by ear and never learned how to read music.[56][57] He got his first break in 1935 when his mother persuaded a local singing group, the Three Flashes, to let him join. Fred Tamburro, the group's baritone, stated that "Frank hung around us like we were gods or something", and admitted that they only took him on board because he owned a car and could chauffeur the group around. Sinatra soon learned that the group were looking to audition for the Major Bowes Amateur Hour show, and "begged" the group to let him in on the act.[58] With Sinatra, the group became known as the Hoboken Four, and they sufficiently impressed Edward Bowes enough for him to ask for them to appear on his show. They each earned $12.50 for the appearance,[59] and ended up attracting 40,000 votes and won first prize—a six-month contract to perform on stage and radio across the United States.[60] Sinatra quickly became the group's lead singer, and much to the jealousy of his fellow group members, garnered most of the attention from girls.[61][c] He spent lavishly on the latest designer pin-striped suits and clothing, aided by friend Nick Sevano, who worked at De Santos tailors in Hoboken.[62] He later admitted that the clothing made him feel wealthy and important, bolstering his ego.[63] Due to the success of the group, Bowes kept asking for them to return, disguised under different names, varying from "The Seacaucus Cockamamies" to "The Bayonne Bacalas".[37] In early 1936, Dolly "footed the bill for a $65 portable public-address system", which could be used by her son for performing in public.[64][d]

Harry James in 1942

Bandleader Harry James had an engagement at the Paramount Theatre in New York in June 1939. One evening after his show, James was listing to a program on WNEW radio called "Dance Band Parade" which consisted of a series of remote broadcasts. James heard a voice on the program which was of much interest to him; the announcer did not identify the male singer and the vocalist did not sing another song during the program. James was able to find out that the vocalist was with Harold Arlen's Band and that they were from the Rustic Cabin in Englewood, New Jersey. When James went to the Rustic Cabin asking about the singer, he was told that the club had no singer, but they did have an emcee who did some singing. After James had heard more of Sinatra's singing, he asked Sinatra to meet with him at the Paramount and a two-year contract of $75 a week was signed.[66][67] The only sticking point was that James wanted Sinatra to change his name to Frankie Satin, as he thought that Sinatra sounded too Italian.[67] Sinatra, nor his mother, would agree to this; he told James that his cousin, Ray Sinatra, was a bandleader in Boston, kept his own name and was doing well with it. James knew of Ray Sinatra, so he did not press any further to get him to change his name.[68][69][e]

It was with the James band that Sinatra released his first commercial record "From the Bottom of My Heart" in July 1939 – US Brunswick No. 8443 and UK Columbia #DB2150. Fewer than 8,000 copies of the record were sold. Sinatra released ten commercial tracks with James through 1939, including "All or Nothing At All" which had weak sales on its initial release, but then sold millions of copies when re-released by Columbia at the height of Sinatra's popularity a few years later.[71] After three months, Sinatra became increasingly frustrated with the status of the James band, feeling that he was not achieving the major success and acclaim he was looking for. His pianist and close friend Hank Sanicola persuaded him to stay with the group, and in September 1939 journalist George T. Simon of Metronome was approached by the band's manager, Jerry Barrett, begging him to give Sinatra a good write-up, because he "wants it more than anybody I've ever seen".[72] In one interview with a reporter, Harry James said "The kid's name's Sinatra. He considers himself the greatest vocalist in the business, Get that! No one ever heard of him. He's never had a hit record. He looks like a wet rag. But he says he is the greatest. If he hears you compliment him, he'll demand a raise tonight..."[73] Thanks to his vocal training, Sinatra could now sing two tones higher, and developed a repertoire which included songs such as "My Buddy", "Willow Weep for Me", "It's Funny to Everyone But Me", "Here Comes the Night", "On a Little Street in Singapore", "Ciribiribin" and "Every Day of My Life".[73]

Tommy Dorsey years (1939–42)[edit]

In November 1939, in a meeting at the Palmer House in Chicago, attended by many of the prominent groups of the time, Sinatra was slipped a note by bandleader Tommy Dorsey asking him to visit him in suite. Dorsey had not recognized him from an earlier audition which had been a disaster for Sinatra, in which he had "cut out completely—dead" after becoming starstruck.[74] Dorsey asked Sinatra to join his band for $125 a week as a replacement for Jack Leonard,[f] who had recently left to launch a solo career. This meeting was a turning point in Sinatra's career, and he knew it would be the band that would make him a star.[75] By signing with Dorsey's band, one of the biggest bands at the time, he greatly increased his visibility with the American public. Though Sinatra was still under contract with James, James recognized the opportunity Dorsey offered and graciously released Sinatra from his contract.[76] Sinatra recognized his debt to James throughout his life, and upon hearing of James' death in 1983, stated: "he [James] is the one that made it all possible."[77]

"The only two people I've ever been afraid of are my mother and Tommy Dorsey".[78]


On January 26, 1940, Sinatra made his first public appearance with the Dorsey band at the Coronado Theatre in Rockford, Illinois.[79] Dorsey recalled: You could almost feel the excitement coming up out of the crowds when the kid stood up to sing. Remember, he was no matinée idol. He was just a skinny skid with big ears. I used the stand there so amazed I'd almost forget to take my own solos". Dorsey also observed that Sinatra would "take a musical phrase and play it all the way through seemingly without breathing for eight, ten, maybe sixteen bars. How the hell did he do that?" Sinatra later confessed that he regularly swam and held his breath underwater, thinking of song lyrics to increase his breathing power.[80] Dorsey was a major influence on Sinatra and became a father-like figure. He copied his mannerisms and traits, becoming a demanding perfectionist like him, and even adopting his hobby of toy trains. Dorsey got on famously with Dolly, enjoying her cooking, and he was made the godfather of Sinatra's daughter Nancy in June 1940.[81] Dorsey advised Sinatra to listen heavily to Bing Crosby, the only singer that he thought that Sinatra should strive to emulate.[82] According to Kelley, Sinatra and drummer Buddy Rich became bitter rivals, both equally as arrogant, with volatile tempers. Fights broke out between them, and in one incident witnessed by Stafford backstage at the Astor Hotel in New York, Rich called Sinatra a name and Sinatra threw a heavy glass pitcher at his head filled with water and ice, which smashed into one of the posters. In another incident at the Golden Gate Theater in San Francisco, Rich attempted to ram Sinatra against the wall with his high F cymbal.[83]

Drummer Buddy Rich, a bitter rival of Sinatra's

In his first year with Dorsey, Sinatra released more than forty songs, with "I'll Never Smile Again" topping the charts for twelve weeks beginning in mid-July.[84] "I'll Never Smile Again" was the song that made Sinatra a star, placing him higher in the charts than even Connie Haines, Jo Stafford, and The Pied Pipers.[62] Other singles released on the Victor label with Tommy Dorsey include "Imagination", "Our Love Affair" and "Stardust" in 1940, "Oh! Look at Me Now", "Dolores", "Everything Happens to Me" and "This Love of Mine" in 1941, "Just as Though You Were There", "Take Me", "Daybreak" and "There are Such Things" in 1942, and "It Started All Over Again", "In the Blue of Evening" and "It's Always You" in 1943.[85] As his success and popularity grew in 1941, Sinatra kept pushing Dorsey to record some solo songs. Dorsey eventually relented, and on January 19, 1942, Sinatra recorded "Night and Day, "The Night We Called It a Day", "The Song is You" and "Lamplighter's Serenade", with Axel Stordahl as arranger and conductor. Sinatra first heard the recordings at the Hollywood Palladium and Hollywood Plaza and was astounded at how good he sounded. Stordahl recalled: "He just couldn't believe his ears. He was so excited. you almost believed he had never recorded before. I think this was a turning point in his career. I think he began to see what he might do on his own".[86]

Sinatra with arranger Axel Stordahl in the 1940s

After the recordings, Sinatra increasingly felt that he needed to go solo,[87] and while Dorsey had made him a star and given him much of the spotlight, he was hampered by his contract which gave Dorsey 43% of Sinatra's lifetime earnings in the entertainment industry.[88] Sinatra was able to persuade Stordahl to leave Dorsey with him and become his personal arranger, offering him $650 a month, five times the salary of Dorsey.[89] On September 3, 1942, Dorsey bid farewell to Sinatra, reportedly saying as Sinatra left, "I hope you fall on your ass".[88] Dorsey replaced him with singer Dick Haymes.[76] A story appeared in the Hearst newspapers that Sinatra's mobster godfather Willie Moretti coerced Dorsey to let Sinatra out of his contract for a few thousand dollars, holding a gun to his head.[90] The incident started rumors of Sinatra's involvement with the Mafia, and was fictionalized in the book and movie The Godfather.[91] A legal battle ensued, eventually settled in August 1943.[92][g] Dorsey and Sinatra, who had been very close, never patched up their differences before his death in 1956, worsened by the fact that Dorsey occasionally made biting comments to the press such as "he's the most fascinating man in the world, but don't put your hand in the cage".[94] Sinatra later said of his reason for the departure: "The reason I wanted to leave Tommy's band was that Crosby was Number One, way up on top of the pile. In the open field, you might say, were some awfully good singers with the orchestras. Bob Eberly (with Jimmy Dorsey) was a fabulous vocalist. Mr. Como (with Ted Weems) is such a wonderful singer. I thought, if I don't make a move out of this and try to do it on my own soon, one of those guys will do it, and I'll have to fight all three of them to get a position".[88]

The onset of Sinatramania and role in World War II (1942–45)[edit]

The Paramount Theatre in New York City

In May 1941, Sinatra was at the top of the male singer polls in Billboard and Down Beat magazines.[95] His appeal to bobby soxers, as teenage girls of that time were called, revealed a whole new audience for popular music, which had been recorded mainly for adults up to that time.[96] The phenomenon became officially known as "Sinatramania" after his "legendary opening" at the Paramount Theatre in New York on December 30, 1942.[88] According to Nancy Sinatra, Jack Benny later said, "I thought the goddamned building was going to cave in. I never heard such a commotion ... All this for a fellow I never heard of."[97] Sinatra performed for four weeks at the theatre, his act following the Benny Goodman orchestra, after which his contract was renewed for another four weeks by Bob Weitman due to its popularity. He was named by Metronome as the most popular male vocalist in the country in early 1943. He become known as "Swoonatra" or "The Voice", and his fans "Sinatratics". The bobbysoxers organized meetings and sent in masses of letters of adoration, and within a few weeks of the show, some 1000 Sinatra fan clubs had been reported across the US.[98] When Sinatra returned to the Paramount in October 1944, 35,000 fans caused a near riot outside the venue because they were not allowed in.[99] It wasn't long before Sinatra was being blamed by New York officials for runaway girls and truancy, and according to Kelley, the education commissioner of New York City considered pressing charges against him.[100] Sinatra later said of the bobbysoxer craze: "I was—I was everything. Happy. I don't know. I wasn't unhappy, let's put it that way. I never had it so good. Sometimes I wonder whether anybody ever had it like I had it, before or since. It was the darndest thing wasn't it?".[101] Sinatra's publicist, George Evans, encouraged interviews and photographs with fans, and was the man responsible for depicting Sinatra as living the American Dream, a vulnerable, shy, sincere Italian American with a rough childhood, a "Depression child who knew only poverty and deprivation", who came good.[102]

During the musicians' strike of 1942–44, Columbia Records re-released Harry James and Sinatra's version of "All or Nothing at All" (music by Arthur Altman and lyrics by Jack Lawrence), recorded in August 1939 and released before Sinatra had made a name for himself.[77] When the recording was re–released in 1943 with Sinatra's name prominently displayed, the record was on the best–selling list for 18 weeks and reached number 2 on June 2, 1943.[103] Sinatra signed with Columbia as a solo artist on June 1, 1943, and he initially had great success, particularly during the 1942–44 musicians' strike.[104] Although no new records had been issued during the strike, he had been performing on the radio on Your Hit Parade from February 1943 until December 1944,[105] and on stage. Columbia wanted new recordings of their growing star as quickly as possible, so Alec Wilder was hired as an arranger and conductor for several sessions with a vocal group called the Bobby Tucker Singers.[106] These first sessions were on June 7, June 22, August 5, and November 10, 1943. Of the nine songs recorded during these sessions, seven charted on the best–selling list.[107] A successful concert in the Wedgewood Room of the prestigious Waldorf-Astoria New York secured his popularity in New York high society.[108] Sinatra released "You'll Never Know", "Close to You", "Sunday, Monday, or Always" and "People Will Say We're in Love" as singles, and the end of 1943 he was more popular in a Downbeat poll than Bing Crosby, Perry Como, Bob Eberly and Dick Haymes.[109] In 1944 Sinatra released "I Couldn't Sleep a Wink Last Night" as a single and recorded his own version of Crosby's "White Christmas".[110]

Sinatra in a radio interview with Italian actress Alida Valli

Sinatra did not serve in the military during World War II. On December 11, 1943, he was classified 4-F ("Registrant not acceptable for military service") for a perforated eardrum by his draft board. Also reported in army files was that Sinatra was "not acceptable material from a psychiatric viewpoint", but the physical eardrum condition was cited instead of emotional instability as the issue to avoid "undue unpleasantness for both the selectee and the induction service".[111] His exemption status occasionally resurfaced from certain critics, often Democrat pundits who resented his endorsement of Republican candidates when he turned Republican in the early 1970s. Biographers have noted that the singer actively supported the war effort (much as Bing Crosby and Bob Hope did, although both were much older), via USO shows and other actions in support of the military during and after WWII.[112] Briefly, there were rumors reported by columnist Walter Winchell,[113] that Sinatra paid $40,000 to avoid the service – but the FBI found this to be without merit.[114][115] Kelley claimed that Sinatra privately confided to columnist Earl Wilson that he would lose more than $300,000 of contracts if he had served during the war.[116]

Towards the end of the war, Sinatra entertained the troops during several successful overseas USO tours with comedian Phil Silvers.[117] During one trip to Rome he met the Pope, who asked him if he was an operatic tenor.[118] Sinatra worked frequently with the popular Andrews Sisters, both on radio in the 1940s, appearing as guests on each other's shows,[119] as well as on many USO shows broadcast to troops via the Armed Forces Radio Service (AFRS).[120] He appeared as a special guest in the sisters' ABC Eight-to-the-Bar Ranch series,[121] while the trio in turn guested on his Songs by Sinatra series on CBS.[122]

In 1945, Sinatra released "I Dream of You (More Than You Dream I Do)", "Saturday Night (Is the Loneliest Night of the Week)", "Dream" and "Nancy (with the Laughing Face)" as singles.[110]

Columbia years (1946–50)[edit]

Sinatra in 1947

According to biographer John Frayn Turner, "The three aspects of his persona progressed in parallel through 1946: his professional life, his social outlook, and his family connections".[123] He released "Oh! What it Seemed to Be", "Day by Day", "They Say It's Wonderful", "Five Minutes More" and "The Coffee Song" as singles,[124] and launched his first album, The Voice of Frank Sinatra.[125] He was soon selling ten million records a year.[126] Such was Sinatra's command at Columbia that his love of conducting was indulged with the release of the set Frank Sinatra Conducts the Music of Alec Wilder, an offering unlikely to appeal to Sinatra's core fanbase at the time consisting of teenage girls.[127]

In 1947, Sinatra released his second album, Songs by Sinatra, originally released as a set of four 78 rpm records. It features songs of a similar mood and tempo such as Irving Berlin's "How Deep is the Ocean?", Harold Arlen's "Over The Rainbow", George Gershwin's "Embraceable You" and Jerome Kern's "All The Things You Are", and is presented in such a way that it is considered his first "concept album".[128] "Mam'selle", composed by Edmund Goulding with lyrics by Mack Gordon for the film The Razor's Edge (1946),[129] was released a single.[124] Sinatra had competition; versions by Art Lund, Dick Haymes, Dennis Day, and The Pied Pipers also reached the top ten of the Billboard charts.[130]

In May 1949, Sinatra was dropped from Your Hit Parade. His new album, Frankly Sentimental, a compilation of eight recordings between 1946 and 1947,[131] was panned by Downbeat, who commented that "for all his talent, it seldom comes to life".[132] He released "The Huckle Buck" as a single, which made the top ten,[133] his last single release under the Columbia label.[124] Starting in September 1949, the BBD&O advertising agency produced a radio series starring Sinatra for its client Lucky Strike called "Light Up Time" – some 176 15-minute shows which featured Frank and Dorothy Kirsten singing – which lasted through to May 1950.[134][135]

Career slump and move to Las Vegas (1950–52)[edit]

Sinatra in November 1950

Sinatra's career and appeal to new teen audiences declined as he moved into his mid-30s. By the end of 1948, Sinatra felt that his career was stalling, something that was confirmed when he slipped to No. 4 on Down Beat's annual poll of most popular singers (behind Billy Eckstine, Frankie Laine, and Bing Crosby).[136] By the following year, Sinatra was pushed out of the top spots in polls for the first time since 1943, and his records were no longer the most popular on the jukeboxes.[132] Cementing the low of his career was the death of publicist George Evans from a heart attack in January 1950 at just 48.[h] Evans had been crucial to Sinatra's career and popularity with the bobbysoxers, and the two had a father-son relationship. According to Jimmy Van Heusen, Sinatra's close friend and songwriter, Evans's death to him was "an enormous shock which defies words".[137]

Sinatra's reputation continued to decline as reports broke out in February 1950 of his affair with Ava Gardner and the destruction of his marriage to Nancy, though Sinatra responded by saying that his marriage had long been over even before he'd met Gardner.[138] In April 1950, Sinatra was engaged to perform at the Copa club in New York, but had to cancel five days of the booking due to suffering a submucosal hemorrhage of the throat. He showed up on the sixth day, still without his voice, humiliating himself in front of the audience, only turning up because he knew that Lee Mortimer had bet Jack Entratter $100 that he wouldn't complete the engagement.[139] Sinatra was forced to cancel his remaining Copa performances and take a two week vacation with Gardner on the Spanish Mediterranean coast, to recover.[140]

The Desert Inn, Las Vegas

In financial difficulty following his divorce and career decline, Sinatra was forced to borrow $200,000 from Columbia to pay his back taxes after MCA refused to front the money.[141] Rejected by Hollywood, he turned to Las Vegas and made his debut at the Desert Inn in September 1951,[142] becoming one of its pioneer entertainers.[143] He also began singing at the Riverside Hotel in Reno, Nevada.[144] Biographer Arnold Shaw remarked that "If Las Vegas had not existed, Sinatra could have invented it". He quoted reporter James Bacon in saying that Sinatra was the "swinging image on which the town is built", adding that no other entertainer quite "embodied the glamour" associated with Las Vegas as him.[142] Sinatra became a prominent figure on the Vegas scene throughout the 1950s and 1960s, a period described by Rojek as the "high-water mark" of Sinatra's "hedonism and self absorption". Rojek notes that the Rat Pack "provided an outlet for gregarious banter and wisecracks", but argues that it was Sinatra's vehicle, possessing an "unassailable command over the other performers". Dean Martin referred to Sinatra's authoritative presence as "Frank's World".[145]

In October 1951, the second season of The Frank Sinatra Show began on CBS Television. Ultimately, Sinatra did not find the success on television for which he had hoped.[i] Santopietro writes that Sinatra "simply never appeared fully at ease on his own television series, his edgy, impatient personality conveying a pent up energy on the verge of exploding".[147]

Sinatra's decline in popularity was evident at his concert appearances. At a brief run at the Paramount in New York he drew small audiences.[148] At the Desert Inn in Las Vegas he performed to half-filled houses of wildcatters and ranchers.[149] At a concert at Chez Paree in Chicago, only 150 people in a 1,200-seat capacity venue turned up to see him.[150] Sinatra's relationship with Columbia Records was also disintegrating, with A&R executive Mitch Miller claiming he "couldn't give away" the singer's records.[148][j] However, there were many "great records" during this time period through the Sinatra-Stordahl pairing. The January 1952 recording of "If I Could Write a Book" has been noted for its particular sensitivity, and has been called a "turning point" that forecasts Sinatra's later, careful work with Jenkins and Riddle.[153] Sinatra's last studio recording for Columbia, "Why Try To Change Me Now", was made in New York on September 17, 1952, with orchestra arranged and conducted by Percy Faith.[155] Columbia and MCA dropped him later that year.[156] Journalist Burt Boyer observed, "Sinatra had had it. It was sad. From the top to the bottom in one horrible lesson."[148] Sinatra would claim that it was he that quit Columbia, because of the "corny things — gimmicks" that Miller wanted him to do.[157]

Rebirth of career and Capitol years (1953–62)[edit]

Nelson Riddle, Sinatra's album arranger for Capitol Records

On October 4, 1953, Sinatra made his first performance at the Sands Hotel and Casino,[158] after an invitation by the manager Jack Entratter, a man Sinatra had known earlier from the days when he worked at the Copa in New York.[159] Sinatra typically performed there three times a year, and later acquired a share in the hotel.[k][162] It was also in 1953 that Sinatra starred in the NBC radio program Rocky Fortune, portraying Rocco Fortunato (a.k.a. Rocky Fortune), a "footloose and fancy free" temporary worker for the Gridley Employment Agency who stumbles into crime-solving. The series aired on NBC radio Tuesday nights from October 1953 to March 1954.[163] That year, Sinatra signed with Capitol Records, where he worked with many of the finest musical arrangers of the era, most notably Nelson Riddle, Gordon Jenkins, and Billy May.[164] Sinatra's split with Gardner in the fall of 1953 had a profound impact on the types of songs he sang and his voice. He began to console himself in songs with a "brooding melancholy", such as "I'm a Fool to Want You", "Don't Worry 'Bout Me", "My One and Only Love" and There Will Never Be Another You".[165] Author John Lahr comments that the new Sinatra was "not the gentle boy balladeer of the forties. Fragility had gone from his voice, to be replaced by a virile adult's sense of happiness and hurt". He quoted Nelson Riddle as saying "It was Ava who did that, who taught him how to sing a torch song. That's how he learned. She was the greatest love of his life and he lost her, and Sinatra as declaring "You have to scrape bottom to appreciate life and start living again".[166] Riddle found Sinatra to be a "perfectionist who drove himself and everybody around him relentlessly", and stated that his collaborators approached him with a sense of uneasiness because of his unpredictable and often volatile temperament.[167] Unlike many of his contemporaries, Sinatra insisted upon direct input regarding arrangements and tempos for his recordings. He would spend weeks thinking about the songs he wanted to record, and would keep an arranger in mind for each song. If it were a mellow love song, he would ask for Gordon Jenkins. If it were a "rhythm" number, he would think of Billy May, or perhaps Neil Hefti or some other favored arranger. Jenkins considered Sinatra's musical sense to be unerring. Sinatra's changes to Riddle's charts would frustrate Riddle, yet he would usually concede that Sinatra's ideas were superior.[168]

Sinatra's career at the time was facilitated by developments in technology. As disc jockey Jonathan Schwartz said, "Never before had there been an opportunity for a popular singer to express emotions at an extended length". In the words of Lahr, "as many as sixteen songs could be held by the twelve-inch L.P., and this allowed Sinatra to use song in a novelistic way, turning each track in a kind of chapter, which built and counterpointed moods to illuminate a larger theme".[169]

Santopietro notes that Sinatra appeared to bury himself in his work in the mid 1950s, with an "unparalleled frenetic schedule of recordings, movies and concerts".[170] In 1954, Sinatra released his first album under the Capitol label, "Songs for Young Lovers", which like subsequent albums was produced by Voyle Gilmore and arranged by Nelson Riddle.[171] It features songs such as "My Funny Valentine", "A Foggy Day", "Like Someone in Love", "I Get a Kick Out of You", "They Can't Take That Away from Me" and "Violets for Your Furs",[171] which became staples of his later concerts.[172][37] His second album Swing Easy!, featuring songs such as "Just One of Those Things", "I'm Gonna Sit Right Down (And Write Myself a Letter)", "Wrap Your Troubles in Dreams", "Taking a Chance on Love" and "Get Happy".[173] was named Album of the Year by Billboard. They also awarded "Young at Heart", the title song of his 1954 film with Doris Day), with Song of the Year.[174] That year he was also named "Top Male Vocalist" by Billboard, Down Beat and Metronome.[174][175][176] Sinatra and Day released an album together to accompany the film, of the same name which peaked at #11 on Billboard, while the single reached #2 and was considered as Sinatra's comeback single after several years away from the top of the pop singles chart.[177][178][179][l] So popular was the song "Young at Heart" that the film was also titled Young at Heart, having had no title until the song's success.[180] The Young at Heart album released by Day and Sinatra did not include the title song, which Sinatra recorded prior to his film work.[181][m] Sinatra also recorded a version of the song "Three Coins in the Fountain", a "powerful ballad" which was released as a single,[182] written by Jule Styne and Sammy Cahn for the Academy Award-nominated film of that year of the same name.[183]

In 1955 Sinatra released In the Wee Small Hours, his first 12" LP,[184] Another collaboration Riddle resulted in the development of the album Songs for Swingin' Lovers!, which was released in March 1956 and was both a critical and financial success. It featured a recording of "I've Got You Under My Skin" by Cole Porter.[185] Also in 1956, Sinatra sang at Democrat convention, and performed with The Dorsey Brothers for a week soon afterwards at the Paramount Theatre.[186] His February 1956 recording sessions inaugurated the studios at the Capitol Records Building[187] His penchant for conducting was displayed again in 1956's Frank Sinatra Conducts Tone Poems of Color, an instrumental album that has been interpreted to be a catharsis to his failed relationship with Gardner.[188]

Dean Martin and Frank Sinatra in 1958

In 1957, Sinatra released Where Are You? (1957) – his first album in stereo, with Gordon Jenkins,[189] and Come Fly With Me (1957). On 9 June 1957, he performed in a 62 minute concert conducted by Riddle at the Seattle Civic Auditorium,[190] his first appearance in Seattle since 1935.[172] The recording was first released as a bootleg, but in 1999 Artanis Records officially released it as the Sinatra '57 in Concert live album, after Sinatra's death.[191] He formed a three-year $3 million contract with ABC to launch The Frank Sinatra Show, featuring Sinatra and guests in 36 half hour shows. ABC agreed to allow Sinatra's Hobart Productions to keep 60% of the residuals,and bought stock in Sinatra's film production unit, Kent Productions, guaranteeing him $7 million.[192] Though an initial critical success upon its debut on October 18, 1957, it soon attracted negative reviews from Variety and The New Republic, and The Chicago Sun-Times thought that Sinatra and frequent guest Dean Martin "performed like a pair of adult delinquents", "sharing the same cigarette and leering at girls".[193]

In September 1958 Sinatra released Frank Sinatra Sings for Only the Lonely, a stark collection of introspective saloon songs and blues-tinged ballads, was released in September 1958, and proved a huge commercial success, spending 120 weeks on Billboards album chart and peaking at No. 1.[194] Cuts from this LP, such as "Angel Eyes" and "One for My Baby (and One More for the Road)", would remain staples of the "saloon song" segments of Sinatra's concerts.[195] In the words of Kelley, by 1959, Sinatra was "not simply the leader of the Rat Pack" but had "assumed the position of il padrone in Hollywood". He was asked by 20th Century Fox to be the master of ceremonies at a luncheon attended by President Nikita Khrushchev on September 19, 1959.[196]

In 1960, Nice 'n' Easy topped Billboard‍ '​s chart and won critical plaudits.[197][198] Sinatra's fourth and final Timex TV special, Welcome Home Elvis was broadcast in March 1960, which earned massive viewing figures. Sinatra had previously been highly critical of Elvis Presley and rock and roll in the 1950s, describing it as a "deplorable, a rancid smelling aphrodisiac" which "fosters almost totally negative and destructive reactions in young people."[199][n] Later, in efforts to maintain his commercial viability, Sinatra recorded Presley's hit "Love Me Tender" as well as works by Paul Simon ("Mrs. Robinson"), the Beatles ("Something", "Yesterday"), and Joni Mitchell ("Both Sides, Now").[201]

Reprise years, "Retirement" and return (1961-81)[edit]

Sinatra at the Grauman's Chinese Theatre in 1965

Sinatra grew discontented at Capitol and decided to form his own label, Reprise Records. His first album on the label, Ring-a-Ding-Ding! (1961), was a major success, peaking at No.4 on Billboard.[202] The album was released in February 1961, the same month that Reprise Records released Ben Webster's The Warm Moods, Sammy Davis, Jr.'s The Wham of Sam, Mavis River's Mavis and Joe E. Lewis's It is Now Post Time.[203] On September 11 and 12, 1961, Sinatra recorded his final songs for Capitol.[204]

In 1962, Sinatra and Count Basie collaborated for the album Sinatra-Basie.[205] This popular and successful release prompted them to rejoin two years later for the follow-up It Might as Well Be Swing, which was arranged by Quincy Jones.[206] Also in 1962, as the owner of his own record label, Sinatra was able to step on the podium as conductor again, releasing his third instrumental album Frank Sinatra Conducts Music from Pictures and Plays.[207] In 1963, Sinatra released The Concert Sinatra, an ambitious album with a 73-piece symphony orchestra led by Nelson Riddle. The concert was recorded on a motion picture scoring stage with the use of multiple synchronized recording machines that employed 35 mm magnetic film.[208] In 1964 the song "My Kind of Town" was nominated for the Academy Award for Best Original Song.[209]

In June 1965, Sinatra, Sammy Davis, Jr., and Dean Martin played live in St. Louis to benefit Dismas House, a prisoner rehabilitation and training center with nationwide programs that in particular helped serve African Americans. The Rat Pack concert was broadcast live via satellite to numerous movie theaters across America.[210] That year, That's Life appeared, with both the single and album becoming Top Ten hits in the US on Billboard's pop charts.[211] Strangers in the Night went on to top the Billboard and UK pop singles charts,[212][213] winning the award for Record of the Year at the Grammys.[214] Released in September 1965 was September of My Years, which won the Grammy Award for best album of the year.[215] One of the album's singles, "It Was a Very Good Year", won the Grammy Award for Best Vocal Performance, Male in 1966.

A career anthology, A Man and His Music, followed in November, winning Album of the Year at the Grammys in 1966. The TV special, Frank Sinatra: A Man and His Music, garnered both an Emmy award and a Peabody Award.[216]

The Sands

Sinatra's first live album release at the time, Sinatra at the Sands, was recorded during January and February 1966 at the Sands Hotel and Casino in Las Vegas. Sinatra was backed by the Count Basie Orchestra, with Quincy Jones conducting.[217] He pulled out from the Sands the following year, when he was driven out by its new owner Howard Hughes, who still resented Sinatra for marrying Ava Gardner.[218] Hughes plotted to rid of Sinatra from the Sands for good, and asked Robert Maheu to draw up a plan shortly after the new hotel opened in 1967. The hotel imposed restrictions on what Sinatra could gamble in the casino, to just $3000 a night.[219][o] Fuming, Sinatra began what The Los Angeles Times describes as a "weekend-long tirade" against the "hotel's management, employees and security forces".[221] It culminated when Sinatra reportedly drove a golf cart through the window of the coffee shop where casino manager Carl Cohen was seated and began "screaming obscenities and anti-Semitic remarks" at Cohen.[222][p] Sinatra reportedly punched Cohen, a heavily built man, who responded with a smack in the mouth, bloodying Sinatra's nose and knocking two of his teeth out.[224] As a result, Sinatra never performed at the Sands again while Hughes owned it, and began performing at Caesar's Palace.[222] A number of the staff were not disappointed to see Sinatra leave the Sands. Numerous employees had been humiliated or intimidated by the Rat Pack over the years, including a busboy that Sinatra tripped up while he was carrying a tray with dishes.[225] After Sinatra left, the mobsters pulled out of Sands and gradually left Vegas in the 1970s.[226]

Sinatra started 1967 with a series of recording sessions with Antônio Carlos Jobim. He later worked with Jobim and Ella Fitzgerald on the TV special, A Man and His Music + Ella + Jobim, which was broadcast on CBS on November 13.[227] Also in 1967, a duet with daughter Nancy, "Somethin' Stupid", topped the Billboard pop and UK singles charts.[212][228] In December, Sinatra collaborated with Duke Ellington on the album Francis A. & Edward K..[229]

During the late 1960s, press agent Lee Solters would invite columnists and their spouses into Sinatra's dressing room just before he was about to go on stage. The New Yorker recounted that "the first columnist they tried this on was Larry Fields of the Philadelphia Daily News, whose wife fainted when Sinatra kissed her cheek. 'Take care of it, Lee,' Sinatra said, and he was off." The professional relationship Sinatra shared with Solters focused on projects on the west coast while those focused on the east coast were handled by Solters' partner, Sheldon Roskin of Solters/Roskin/Friedman, a well-known firm at the time.[230]

With Sinatra in mind, singer-songwriter Paul Anka wrote the song "My Way", inspired by the French "Comme d'habitude" ("As Usual"), composed by Claude François and Jacques Revaux. Sinatra first recorded just after Christmas 1968.[231] "My Way", over the years, become Sinatra's definitive, best-known song on the Reprise label, but it wasn't a major success initially when released as a single in 1969, charting at #27 in the US and #5 in the UK.[232]

Watertown was one of Sinatra's most acclaimed concept albums, released that year, with music by Bob Gaudio (of the Four Seasons) and lyrics by Jake Holmes.[233] However, it sold a mere 30,000 copies in 1970 and reached a peak chart position of 101, putting an end to plans for a television special based on the album.[234] Watertown was one of the only recording sessions having Sinatra sing against pre-recorded tracks instead of a live orchestra.[235] On November 2, 1970, Sinatra recorded the last songs for Reprise Records before his self-imposed retirement.[236] One of the songs recorded during the session, "The Game is Over", was written by John Denver.[237]

On June 13, 1971, at a concert in Hollywood to raise money for the Motion Picture and TV Relief Fund, at the age of 55, Sinatra announced that he was retiring. When responding to press reports that poor health or terminal illness was the reason he responded: "My health is spectacular. In fact it's never been better. That's why those goddamn rumors burn me so. It shows the irresponsibility of the American press".[238] While he was in retirement, President Richard Nixon asked him to perform at a Young Voters Rally in anticipation of the upcoming campaign. Sinatra obliged and chose to sing "My Kind of Town" for the rally held in Chicago on October 20, 1972.[239]

Frank Sinatra, with Giulio Andreotti (left), President Richard Nixon and First Lady Pat Nixon at the White House, 1973

In 1973, Sinatra came out of his short-lived retirement with a television special and album, both entitled Ol' Blue Eyes Is Back.[234] The album, arranged by Gordon Jenkins and Don Costa,[240] was a success, reaching number 13 on Billboard and number 12 in the UK.[241][242] The TV special was highlighted by a dramatic reading of "Send in the Clowns" and a song-and-dance sequence with former co-star Gene Kelly.[243]

The following January, Sinatra returned to Las Vegas, performing at Caesars Palace despite vowing in 1970 never to play there again after the manager of the resort, Sanford Waterman, pulled a gun on him during a heated argument.[244] In Australia, he caused an uproar by describing journalists there – who were aggressively pursuing his every move and pushing for a press conference – as "fags", "pimps", and "whores". Australian unions representing transport workers, waiters, and journalists went on strike, demanding that Sinatra apologize for his remarks. Sinatra instead insisted that the journalists apologize for "fifteen years of abuse I have taken from the world press". The future Prime Minister of Australia, Bob Hawke, then the Australian Council of Trade Unions (ACTU) leader, also insisted that Sinatra apologize, and a settlement was eventually reached to the apparent satisfaction of both parties.[245]

In October 1974, Sinatra appeared at New York City's Madison Square Garden in a televised concert that was later released as an album under the title The Main Event – Live. Backing him was bandleader Woody Herman and the Young Thundering Herd, who accompanied Sinatra on a European tour later that month.[246][247] The following August, Sinatra held several consecutive concerts at Lake Tahoe together with the newly-risen singer John Denver,[248][249] who became a frequent collaborator.[250] Denver later appeared as a guest in the Sinatra and Friends ABC-TV Special, singing "September Song" as a duet.[251] Sinatra covered the John Denver hits "My Sweet Lady" and "Leaving on a Jet Plane", arranged for him by Eumir Deodato.[252] According to Denver, his song "A Baby Just Like You" was written at Sinatra's request, due to the birth of his grandchild Angela, which gave Sinatra a new outlook on life and meaning.[253]

During Labor Day weekend 1976 Sinatra was responsible for reuniting old friends and comedy partners Dean Martin and Jerry Lewis for the first time in nearly twenty years.[254] Sinatra performed for the "Jerry Lewis MDA Telethon" that afternoon and before he performed he brought Martin out on stage.[255] In 1979, Sinatra performed in front of the Egyptian pyramids for Anwar Sadat, which raised more than $500,000 for Sadat's wife's charities.[256] Back in Las Vegas, while celebrating 40 years in show business and his 64th birthday, he was awarded the Grammy Trustees Award during a party at Caesars Palace.[257][258]

In 1980, Sinatra's first album in six years was released, Trilogy: Past Present Future, a highly ambitious triple album that found Sinatra recording songs from the past (pre-rock era) and present (rock era and contemporary) that he had overlooked during his career, while 'The Future' was a free-form suite of new songs linked à la musical theater by a theme, in this case, Sinatra pondering over the future.[259] The album garnered six Grammy nominations – winning for best liner notes – and peaked at number 17 on Billboard's album chart,[259] while spawning yet another song that would become a signature tune, "Theme from New York, New York",[260] as well as Sinatra's much lauded (second) recording of George Harrison's "Something" (the first was not officially released on an album until 1972's Frank Sinatra's Greatest Hits, Vol. 2).[261]

The following year, Sinatra built on the success of Trilogy with She Shot Me Down, an album that revisited the dark tone of his Capitol years, and was praised by critics as a vintage late-period Sinatra. Sinatra would comment that it was "A complete saloon album ... tear-jerkers and cry-in-your-beer kind of things".[262] Also in 1981, Sinatra was embroiled in controversy when he worked a ten-day engagement for $2 million in Sun City, in the internationally unrecognized Bophuthatswana, breaking a cultural boycott against apartheid-era South Africa. Botswana's president, Lucas Mangope, awarded Sinatra with Botswana's highest honor, the Order of the Leopard, and made him an honorary tribal chief.[263]

Later career (1982–death)[edit]

Sinatra signed a $16 million three-year deal with the Golden Nugget Las Vegas in 1982

In 1982, Sinatra signed a $16 million three-year deal with the Golden Nugget of Las Vegas. Kelley notes that by this period Sinatra's voice had grown "darker, tougher and loamier", but he "continued to captivate audiences with his immutable magic". She added that his baritone voice "sometimes cracked, but the gliding intonations still aroused the same raptures of delight as they had at the Paramount Theater".[264] That year he made a reported further $1.3 million from the Showtime television rights to his "Concert of the Americas" in the Dominican Republic, $1.6 million for a concert series at Carnegie Hall, and $250,000 in just one evening at the Chicago Fest. He donated a lot of his earnings to charity.[265]

Sinatra was selected as one of the five recipients of the 1983 Kennedy Center Honors, alongside Katherine Dunham, James Stewart, Elia Kazan, and Virgil Thomson. Quoting Henry James, President Reagan said in honoring his old friend that "art was the shadow of humanity" and that Sinatra had "spent his life casting a magnificent and powerful shadow".[266] On September 21, 1983, Sinatra filed a $2 million court case against Kitty Kelley, suing her in punitive damages, before her unofficial biography, His Way, was even published. Kelley claims that in writing it, she "began trying to read everything ever written about Sinatra", an "enormous task", given the depth of his 40-year career, and conducted 857 interviews to prepare for it.[267] The book became a best-seller for "all the wrong reasons" and "the most eye-opening celebrity biography of our time", according to William Safire of The New York Times.[268] Sinatra was always adamant that such a book would be written on his terms, and he himself would "set the record straight" in details of his life.[269] According to Kelley, the family detested her and the book, which took its toll on Sinatra's health. Kelley claims that Tina Sinatra blamed her for her father's colon surgery in 1986.[270] He was forced to drop the case on September 19, 1984, with several leading newspapers expressing concerns about his views on censorship.[271]

Sinatra in 1989

In 1984, Sinatra worked with Quincy Jones for the first time in nearly two decades on the album, L.A. Is My Lady, which was well received critically.[272] The album was a substitute for another Jones project, an album of duets with Lena Horne, which had to be abandoned.[273][q]

From the late 1980s, one of Sinatra's favorite haunts in Los Angeles was Nicky Blair's, an Italian restaurant on the Sunset Strip, where Sinatra and the Rat Pack would play poker in the kitchen to escape fans and the press.[274]

In 1990 Sinatra was awarded the second "Ella Award" by the Los Angeles-based Society of Singers, and performed for a final time with Ella Fitzgerald at the award ceremony.[275] Sinatra maintained an active touring schedule in the early 1990s, performing 65 concerts in 1990, 73 in 1991 and 84 in 1992 in seventeen different countries.[12] In 1993, Sinatra returned to Capitol Records and the recording studio for Duets. The album and its sequel, Duets II, would see Sinatra remake his classic recordings with popular contemporary performers, who added their vocals to a pre-recorded tape.[12]

Sinatra with Brendan Grace in 1991

During his tours in the early 1990s, his memory failed him at times during concerts, and he happened to faint onstage in Richmond, Virginia in March 1994.[276] His final public concerts were held in Fukuoka Dome in Japan on December 19–20, 1994.[277] The following year, on February 25, 1995, at a private party for 1200 select guests on the closing night of the Frank Sinatra Desert Classic golf tournament, Sinatra sang before a live audience for the very last time.[278] Esquire reported of the show that Sinatra was "clear, tough, on the money" and "in absolute control".[279] His closing song was "The Best is Yet to Come", and he exclaimed to Tom Dreesen as he walked off stage, "Don't Put Away That Suitcase".[278]

Sinatra was awarded the Legend Award at the 1994 Grammy Awards, where he was introduced by Bono, who said of him, "Frank's the chairman of the bad attitude ... Rock 'n roll plays at being tough, but this guy is the boss – the chairman of boss ... I'm not going to mess with him, are you?"[280] Sinatra called it "the best welcome ... I ever had", but his acceptance speech ran too long and was abruptly cut off, leaving him looking confused and talking into a dead microphone.[281]

In 1995, to mark Sinatra's 80th birthday, the Empire State Building glowed blue.[282] A star-studded birthday tribute, Sinatra: 80 Years My Way, was held at the Shrine Auditorium in Los Angeles, featuring performers such as Ray Charles, Little Richard, Natalie Cole and Salt-N-Pepa singing his songs.[283] At the end of the program Sinatra graced the stage for the last time to sing the final notes of the "Theme from New York, New York" with an ensemble.[284] In recognition of his many years of association with Las Vegas, Frank Sinatra was elected to the Gaming Hall of Fame in 1997.[285]

Film career[edit]

Sinatra in 1945

Early career (1941-52)[edit]

Sinatra tried to break into Hollywood in the early 1940s, and spent much time visiting the sets and watching directors and actors in action.[286] He was rarely enthusiastic towards acting; during his early career he stated to a reporter that "pictures stink", but later claimed that he was misquoted.[287] Sinatra made his film debut in 1941, performing in an uncredited sequence in Las Vegas Nights, singing "I'll Never Smile Again" with Tommy Dorsey's The Pied Pipers.[288] In 1943 he had a cameo role along with the likes of Duke Ellington and Count Basie in Charles Barton's Reveille with Beverly, making a brief appearance singing "Night and Day".[289] The following year he was given his first leading role opposite Michèle Morgan and Jack Haley in 1944 in Tim Whelan's musical film Higher and Higher for RKO Pictures, playing himself.[290][291] He again worked with Whelan in another musical of that year, Step Lively, co-starring George Murphy and Adolphe Menjou. Biographer Tim Knight wrote that that this was the film that Hollywood "fully unleashed 'The Voice' on the movies", giving Sinatra a role as a "sweetly naive playwright who is swept into scheming Broadway director's Gordon Miller's chaotic universe".[292]

Sinatra in Till the Clouds Roll By (1946)

In 1945, Metro-Goldwyn-Mayer cast Sinatra opposite Gene Kelly and Kathryn Grayson in the Technicolor musical Anchors Aweigh, in which he played a sailor on leave in Hollywood for four days.[293][294] A major success,[295] it garnered several Academy Award wins and nominations, and the song "I Fall in Love Too Easily", sung by Sinatra in the film, was nominated for the Academy Award for Best Original Song.[296] Knight notes that while the film "drew Sinatra's young, excitable fans", it also "attracted an older audience who never would have stood in line all night just to hear him sing", making him into a "truly cross generational star".[297] Sinatra expressed "lifelong gratitude" to Kelly for tutoring him in acting and dancing and stated that he was instrumental in overcoming his doubts.[298] In 1946, Sinatra featured in a ensemble cast which included Robert Walker, Judy Garland and Lena Horne in the commercial successful Till the Clouds Roll By, a Technicolor musical biopic of Jerome Kern, directed Richard Whorf.[299][300]

Sinatra in Take Me Out to the Ball Game (1949)

In 1948 Sinatra appeared with Grayson in The Kissing Bandit, playing a shy, Boston-bred son of a robber, who falls for the daughter of the Spanish Governor of California. The film was a financial disaster,[301] and was so poorly received critically, that it is often cited as the worst film of Sinatra's career.[302] He played a priest, one of his most unlikely roles according to Knight, opposite Fred MacMurray and Alida Valli in Irving Pichel's The Miracle of the Bells. Due to press negativity surrounding his alleged Mafia connections at the time, particularly from Lee Mortimer,[r] Evans announced to the public that Sinatra would donate his $100,000 in wages from the film to the church.[304] It fared poorly upon release.[305] The following year, Sinatra co-starred with Gene Kelly in the Technicolor musical Take Me Out to the Ball Game, a film set in 1908, in which Sinatra and Kelly play baseball players who are part-time vaudevillians.[306] He teamed up with Kelly for a third time in On the Town, playing a sailor on leave in New York City. Today the film is rated very highly by critics, and in 2006 it ranked No. 19 on the American Film Institute's list of best musicals.[307]

Sinatra with Gene Kelly and Jules Munshin in On the Town (1949)

After a series of poor reviews in 1949, and his moving to second billing in On the Town, with a sacking from MGM imminent, Sinatra approached Columbia Pictures for a part as Nick in Nicholas Ray's Knock on Any Door. Sinatra felt he was right for the part, given his New Jersey background, but producer David Selznick thought that he was too old for the part at 34, and it was given to John Derek instead.[308] MGM formally parted with Sinatra on April 27, 1950 with a fee of $85,000,[309] a year before the contract was due to expire.[310]

In 1951, Sinatra featured opposite Jane Russell and Groucho Marx in Double Dynamite, an RKO Irving Cummings comedy produced by Howard Hughes. Although Sinatra has by far the most screen time, he took third billing behind Jane Russell and Groucho Marx.[s] The film flopped, and demonstrated that Sinatra's career was in "deep trouble".[312] Joseph Pevney's Meet Danny Wilson with Shelley Winters also failed to make an impression; Knight thought at times it was overacted.[313] For Santopietro, the film marked the end of the first period of Sinatra's film career, at a time when his career had slumped.[314] The New York World Telegram and Sun ran the headline "Gone on Frankie in '42; Gone in '52".[315]

Rebirth of career and acclaim (1953-62)[edit]

Sinatra as Maggio in From Here to Eternity (1953)

The rebirth of Sinatra's career began in 1953 with Fred Zinnemann's drama From Here to Eternity, and based on the novel of the same name by James Jones. The picture deals with the tribulations of three soldiers, played by Burt Lancaster, Montgomery Clift, and Sinatra, stationed on Hawaii in the months leading up to the attack on Pearl Harbor.[316] Sinatra had long been desperate to find a film role which would bring him back into the spotlight, and Columbia Pictures boss Harry Cohn had been inundated by appeals from people across Hollywood to give Sinatra a chance to star as "Maggio" in the film.[317] Initially, Sinatra was sure that Eli Wallach would be given the part, and spent a miserable few weeks on location with Ava Gardner in Africa during the shooting of John Ford's Mogambo.[318] He was eventually cast in the role, accepting a minor fee to "prove his worth".[319][t] During production, Montgomery Clift became a close friend, and Sinatra later professed that he "learned more about acting from him than anybody I ever knew".[321] After several years of critical and commercial decline, his Academy Award for Best Supporting Actor win helped him regain his position as the top recording artist in the world.[322] The Los Angeles Examiner wrote that Sinatra is "simply superb, comical, pitiful, childishly brave, pathetically defiant", commenting that his death scene is "one of the best ever photographed".[323] Sinatra later stated that the "greatest change in my life began the night they gave me that Oscar".[162]

Sinatra in Suddenly (1954)

In 1954 Sinatra starred opposite Doris Day in the musical film Young at Heart,[324] and featured opposite Sterling Hayden in the film noir Suddenly, playing a psychopathic killer posing as an FBI agent who takes over a familial residence during a stakeout. Sinatra's performance was lauded by critics, with Newsweek considering him to have played "one of the most repellent killers in American screen history",[325] and Bosley Crowther of The New York Times noting his "easy, cold, vicious sort of gleam", in stark comparison to his earlier career.[326] Sinatra had wanted to play the lead role in On the Waterfront that year, which eventually went to Marlon Brando. According to Kelley, Sinatra sued producer Sam Spiegel for $500,000 for breach of contract, settled amicably in the end, and labelled Brando the "most overrated actor in the world" in rage.[327]

Sinatra was nominated for an Academy Award for Best Actor and BAFTA Award for Best Actor in a Leading Role for his role as a heroin addict in The Man With The Golden Arm (1955).[328] In preparation for the film he spent time at drug rehabilitation clinics observing addicts going cold turkey.[329] Unlike previous roles, Sinatra found himself deeply immersed in the character and enjoyed rehearsing scenes.[330] Sinatra later remarked that he had always considered his performance in The Man With The Golden Arm to have been the greatest of his film career, and that he'd won the Oscar for the wrong role.[331] This was followed by a role opposite Brando in Guys and Dolls. Sinatra was upset when Brando was given the lead romantic role of Sky Masterson and sued the producers; the case wasn't settled until out of court five years later.[332] He also featured alongside Debbie Reynolds in The Tender Trap,[333] in a role which biographer Roy Pickard considers to have been the film in which "Sinatra at last got into top gear", bringing him back to MGM after a five year absence.[334][335] Later in the year he starred opposite Robert Mitchum and Olivia de Havilland as a hospital orderly in Stanley Kramer's debut picture, Not as a Stranger, for which he was nominated for a BAFTA Award for Best Actor in a Leading Role.[336][337] During production, Sinatra got drunk with Mitchum and Broderick Crawford and trashed Kramer's dressing room.[338] Kramer vowed to never hire Sinatra again at the time.[339]

Sinatra and Grace Kelly on the set of High Society (1956)

Sinatra was cast in the lead role in Henry King's Carousel (1956), a 20th Century Fox production. However, when Sinatra learned that the film was to be shot in two formats, Cinemascope and a new 55-millmeter process, he refused to make "two pictures for the price of one", and walked off the set and didn't return. Fox sued Sinatra for a million dollars for breach of contract and replaced him with Gordon MacRae.[339] They later agreed to drop the case on the condition that Sinatra appear in another film of theirs.[340] In 1956 he featured alongside Bing Crosby and Grace Kelly in High Society for MGM, earning a reported $250,000 for the picture.[341] The public rushed to the cinemas to see Sinatra and Crosby together onscreen, and it ended up earning over $13 million at the box office, becoming one of the highest-grossing pictures of 1956.[342]

In 1957, Sinatra starred opposite Rita Hayworth and Kim Novak in George Sidney's Pal Joey, for which he was nominated for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy. Santopietro considers the scene in which Sinatra sings "The Lady Is a Tramp" to Hayworth to have been the finest moment of his film career.[12] He next portrayed comedian Joe E. Lewis in The Joker Is Wild, a romanticized biopic of his life. Sinatra earned $125,000 for the role through his new company Bristol Productions, which had a 25% share in the film and box-office gross.[343] The song "All the Way" won the Academy Award for Best Original Song.[344] Later that year he spent time on location in Spain shooting The Pride and the Passion with Cary Grant, in which he played a Spanish guerrilla leader during the Peninsular War of 1810.[345] Director Kramer agreed to give Sinatra another chance, and later regretted it, finding him uncooperative and arrogant, as he was unwilling to shoot his scenes twice.[339][u]

Sinatra in Pal Joey (1957)

In 1958, Sinatra was one of the ten biggest box office draws in the United States.[348] He starred opposite Dean Martin,[349] Martha Hyer and Shirley MacLaine in Vincente Minnelli's Some Came Running for MGM. Daniel O'Brien considers it to be "probably the high point of Sinatra's late fifties output".[350] He next appeared in two war pictures: Kings Go Forth (1958) with Tony Curtis and Natalie Wood, a film which dealt with themes of racism and miscegenation,[351][352] and John Sturges's Never So Few (1959), with Gina Lollobrigida, Peter Lawford, and Steve McQueen, based on the OSS Detachment 101 incident in South East Asia during World War II.[353] Davis, Jr. was originally intended to play McQueen's role, but Sinatra fired him in revenge for a mild comment he made about the proverbial "old blue eyes" during a Chicago radio interview.[354] McQueen's biographer Wes D. Gehring claims that Sinatra got on so famously with McQueen during the production, often performing practical jokes on each other, that McQueen "might have become part of the Rat Pack".[355] Sinatra ended the decade with a role as a "lovable small-time operator and hotel keeper" opposite Edward G. Robinson and Eleanor Parker in the Frank Capra comedy, A Hole in the Head, [356][357] filmed on Miami Beach, Florida over the winter of 1958.[358] "High Hopes", sung by Sinatra in the film, won the Academy Award for Best Original Song,[359] and became a chart hit, lasting on the Hot 100 for 17 weeks.[360]

Rat Pack and later roles (1960-80)[edit]

In 1960 Sinatra starred in Can-Can. He personally financed Ocean's Eleven, the first film to feature the Rat Pack together, and paid Martin and Davis Jr. fees of $150,000 and $125,000, exorbitant for the period.[361] In 1962 Sinatra had a leading role in the Academy Award winning The Manchurian Candidate and appeared with the Rat Pack in the western Sergeants 3, following it with 4 for Texas in 1963, which was co-produced by Sinatra, Martin and Robert Aldrich.[361] For his performance in Come Blow Your Horn he was nominated for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy.[362]

Sinatra as Tony Rome

In 1964 he starred in Robin and the 7 Hoods; Sinatra featured in three films in 1965. His first was None but the Brave, which was also the only feature film he directed.[363] His two other films include Marriage on the Rocks and Von Ryan's Express.[364][365] The following year he starred in Assault on a Queen and Cast a Giant Shadow.[366][367] Brad Dexter wanted Sinatra to display the same professional pride in his films as he did his recordings. On one occasion he gave Sinatra Anthony Burgess's novel A Clockwork Orange (1962) to read, with the idea of making a film, but Sinatra thought it had no potential and didn't understand a word.[368][v] In the late 1960s, Sinatra became known for playing detectives, notably Tony Rome in Tony Rome (1967) and its sequel Lady In Cement (1968).[371][372] He also played a similar role in 1968's The Detective.[373]

In 1970, Sinatra starred opposite George Kennedy in the western Dirty Dingus Magee. According to biographer Tom Santopietro, Sinatra only agreed to the film, an "abysmal" affair which was clearly the "wrong vehicle" for him as he put, because he needed something to cheer him up following the death of his father in January 1969.[374] The film was panned by the critics. In a scathing review, Roger Ebert referred to the film as "as shabby a piece of goods as has masqueraded as a Western", and stated: "I lean toward blaming Frank Sinatra, who in recent years has become notorious for not really caring about his movies. If a shot doesn't work, he doesn't like to try it again; he might be late getting back to Vegas".[375] Sinatra's last major film role was opposite Faye Dunaway in Brian G. Hutton's The First Deadly Sin (1980), in which he plays a troubled New York City homicide cop, Captain Edward X. Delaney. The First Deadly Sin failed to make much of an impression at the box office, but was well-received by a number of critics. Santopietro noted that Sinatra gave an "extraordinarily rich", heavily layered characterization, one which "made for one terrific farewell" to his film career,[376] and Ebert was pleasantly surprised by Sinatra's "quiet, poignant, and very effective performance" as the detective, who "looks and acts very touchingly like a tired old cop on the threshold of retirement".[377]

Personal life[edit]


Sinatra had three children, Nancy (born 1940), Frank Jr. (born 1944), and Tina (born 1948), all with his first wife, Nancy Sinatra (née Barbato) (m. 1939–1951). Sinatra had numerous extra-marital affairs, the first of which was with blonde starlet Alora Gooding from October 1940 while in Hollywood, his "first big love away from home" according to Nick Sevano.[378] Next followed Rita Maritt, a 16-year-old Long Island debutante, the daughter of an oil baron, and Mary Lou Watts, a wealthy socialite.[379] Gossip magazines published details of affairs with the likes of Lana Turner and Marilyn Maxwell.[380]

Ava Gardner, Sinatra's wife from 1951 to 1957

Kelley claims that Sinatra had first seen photographs of Ava Gardner in a magazine and had sworn that he would marry her. Ruth Rosenthal, a friend of Gardner's, stated that Gardner initially detested him upon meeting him at MGM, finding him to be "conceited, arrogant and overpowering". Their similarities, however, from vices like smoking, drinking hard liquor and cursing, to their volatile tempers and love of violent sports, soon became apparent.[381] Sinatra separated from Nancy on Valentine's Day 1950, after he confessed to his passionate affair with Gardner, and she subsequently locked him out of the house and hired a lawyer.[138] As Nancy refused to divorce him, Sinatra was eventually granted a divorce in Nevada in October 1951, and subsequently obtained a marriage license in Pennsylvania, marrying Gardner in a small ceremony.[382] A turbulent marriage, with many well-publicized fights and altercations,[383] and an abortion in November 1952,[384] the couple formally announced their separation on October 29, 1953 through MGM.[385] Gardner filed for divorce in 1954, at a time when she was dating matador Luis Miguel Dominguín, but the divorce wasn't settled until 1957.[386] Sinatra blamed Peter Lawford for the split, who had dated Gardner before, and it took six years for Sinatra to forgive him. He was inconsolable in the fall of 1953 after the split, and according to Kelley, on November 18, Van Heusen found him in the elevator of his 57th Street apartment with his wrists slashed.[w][388] Sinatra took responsibility for Gardner's business affairs long after the split, and was still dealing with her finances in 1976.[389] When she fell into financial difficulty in later years, Sinatra paid $50,000 towards her medical bills.[390]

Sinatra was very close to Lauren Bacall. According to Kelley, her husband Humphrey Bogart believed that Sinatra was in love with Bacall and failed to attend the Sands on Bacall's 32nd birthday out of jealousy, though the two men were on good terms.[391] Sinatra and Bacall were frequently seen together in public throughout 1957, and on March 11, 1958 they reportedly became engaged, though Sinatra denied intending to marry her.[392] Sinatra's affair with actress Shirley Van Dyke came to light following her overdose and hospitalization in 1957.[393] In the 1962 he broke off another engagement to Juliet Prowse.[394] Sinatra was later married to Mia Farrow (m. 1966–1968), and finally to Barbara Marx (m. 1976–1998; his death). In a 2013 interview Farrow admitted that Sinatra may be the father of her son, Ronan Farrow (born 1986).[395]


Sinatra in 1957

In his spare time, Sinatra enjoyed listening to classical music, and would attend concerts when he could.[396] He also liked opera, particularly Luciano Pavarotti, and told himself, "I'm just a wop baritone. This guy can really sing".[397] A workaholic, he reportedly only slept for four hours a night on average.[398] Impeccable with his dress[x] and cleanliness, while with the Tommy Dorsey band he developed the nickname "Lady Macbeth", because of frequent showering and switching his outfits.[400] Throughout his life, Sinatra had mood swings and bouts of mild to severe depression,[401] admitting to an interviewer in the 1950s that "I have an over-acute capacity for sadness as well as elation".[402] Avoiding solitude and unglamorous surroundings at all costs, he struggled with the conflicting need "to get away from it all, but not too far away."[403] Anthony Quinn once stated that he had a "cruel streak in his personality", but that he still loved him as he was "what all men are and not one man in a million ever is".[404] Sinatra's mood swings often developed into violence, directed at people he felt had crossed him, particularly journalists who gave him scathing reviews, publicists and photographers. He received negative press for fights with Lee Mortimer in 1947, photographer Eddie Schisser in Houston in 1950, and Judy Garland's publicist Jim Byron in 1954, whom he reportedly referred to as a "fucking parasite".[405] Yet Sinatra was known for his generosity, particularly after his comeback. When Lee J. Cobb nearly died from a heart attack in June 1955, Sinatra flooded him with "books, flowers, delicacies", paid his hospital bills, and visited him daily, telling him that his finest acting was yet to come.[406] In another instance, after a heated argument with manager Bobby Burns, rather than apologize, Sinatra bought him a brand new Cadillac.[67]

In a 1963 interview with Playboy magazine, Sinatra stated that his belief in God was similar to Albert Schweitzer, Bertrand Russell and Albert Einstein in that had a "respect for life – in any form", but didn't believe in "a personal God to whom I look for comfort or for a natural on the next roll of the dice".[407] According to Kelley, he was critical of the church on numerous occasions, and had thought it hypocritical in Hoboken that Italians had to attend a different church from the Irish and Germans.[408] Though turned off by organized religion at times, however, Sinatra had a deep faith that became public when he turned to the Catholic Church for healing after his mother died in a plane crash late in his career. He died as a practicing Catholic and had a Catholic burial.[409]

Cal Neva Lodge[edit]

In 1960, Sinatra bought a share in the Cal Neva Lodge & Casino, straddling the border between Nevada and California on the shores of Lake Tahoe. Though it only opened between June and September, Sinatra built the Celebrity Room theater, which attracted the likes of the other Rat Pack members, Red Skelton, Marilyn Monroe, Victor Borge, Joe E. Lewis, Lucille Ball, Lena Horne, Juliet Prowse, the McGuire Sisters and others. By 1962 he reportedly held a 50% share in the hotel.[410] Sinatra's gambling license was temporarily stripped by the Nevada Gaming Control Board in 1963 after mobster Sam Giancana was spotted on the premises.[411] Due to ongoing pressure from the FBI and Nevada Gaming Commission and mobster control of casinos, and trouble with the Mafia, Sinatra agreed to give up his share in Cal Neva and the Sands.[412]

Alleged organized-crime links[edit]

Mugshot of mobster Lucky Luciano in 1936

Sinatra became the stereotype of the "tough working-class Italian American", something which he embraced. Sinatra commented that if it hadn't been for his interest in music he'd "probably have ended in a life of crime".[413] Kelley claims that Eddie Fisher once remarked that Sinatra "wanted to be a hood" and had once told him that "I'd rather be a don of the Mafia than president of the United States". However, Peter Lawford had said that Sinatra only referred to them as the "boys" or "the Outfit", rather than the "Mafia".[414]

In Sinatra's early days, mafia boss Willie Moretti helped him for kickbacks and was reported to have intervened in releasing him from his contract with Tommy Dorsey.[415] Sinatra was present at the Mafia Havana Conference in 1946.[416] When the press learned of Sinatra being in Havana with Lucky Luciano, one newspaper published the headline, "Shame, Sinatra".[417] Kelley claims that Phyllis McGuire referred to Sam Giancana and Sinatra as the "best of friends", and would often play golf together in Nevada and visit each other. [418] She also quotes Jo-Carrol Silvers in saying that both Sinatra and her husband Phil Silvers "adored Bugsy Siegel so much", and would boast about him to friends and how many people he had killed. She also claimed that Silvers had told her that "like Bugsy, Frank had a Mafia Redneck mentality", with their shared love of high-living and grandiose plans in Las Vegas.[419] Kelley claims that Sinatra and mobster Joseph Fischetti had been good friends from 1938 onward, and acted like "Sicilian brothers".[420] She also states that Sinatra and Hank Sanicola were financial partners with Mickey Cohen, a West Coast mobster, in the gossip magazine Hollywood Night Life, which she claims that Sinatra funded $15,000 into to get back at Hollywood.[421]

Mugshot of Bugsy Siegel in 1928

The Federal Bureau of Investigation (FBI) kept records amounting to 2,403 pages on Sinatra, becoming a natural target with his alleged Mafia ties, his ardent New Deal politics and his friendship with John F. Kennedy.[422] The FBI kept Sinatra under surveillance for almost five decades beginning in the 1940s. The documents include accounts of Sinatra as the target of death threats and extortion schemes.[423] The FBI documented that Sinatra was losing esteem with the Mafia as he grew closer to President Kennedy, whose brother Bobby was leading a crackdown on organized crime. They wiretapped Giancana's conversations, and founded than Giancana no longer trusted Sinatra after he'd been spotted with Kennedy and branded him a liar.[424] Their purported friendship finally came to an end in 1963 following the Nevada Gaming Commission's investigation into the casinos—according to Kelley, Giancana blamed Sinatra for the ordeal and was fuming at the abuse he had given to the commission's chairman, Ed Olsen.[425]

The FBI's secret dossier on Sinatra was released in 1998 in response to Freedom of Information Act requests.[426] Despite the many connections and anecdotes reported, Sinatra frequently denied personal and professional links with organized-crime figures such as Bugsy Siegel, Carlo Gambino, Sam Giancana, Lucky Luciano, and Joseph Fischetti,[427] vehemently declaring that "any report that I fraternised with goons or racketeers is a vicious lie".[428] When asked about his Mafia contacts in 1965 he stated that it was "due to a legitimate reason. We built a hotel together in Las Vegas". In January 1967 Sinatra stood before a Las Vegas grand jury investigating mobster influence in the casinos, and denied any financial exploits with Giancana.[428] In his memoir, Dean & Me, Sinatra's associate Jerry Lewis said of the subject: "In the 1940s and '50s, before the Mob lost its hold on nightclubs and Vegas, it was literally impossible for an entertainer, any entertainer, not to deal with them."[429]

Political views[edit]

Political activities, 1944–69[edit]

Sinatra, pictured here with Eleanor Roosevelt in 1960, was an ardent supporter of the Democratic Party until the early 1970s.

Sinatra held differing political views throughout his life. Sinatra's parents had immigrated to the United States in 1895 and 1897, respectively. His mother, Dolly Sinatra (1896–1977), was a Democratic Party ward leader.[30] In 1944, after sending a letter to President Franklin D. Roosevelt in support of the president's stewardship in wartime, Sinatra was invited to meet Roosevelt at the White House, where he agreed to become part of the Democratic party's voter registration drives, and heavily campaigned for the Democrats in the 1944 presidential election.[430] According to Jo Carroll Silvers, in his younger years Sinatra was an "ardent liberal" who was "so concerned about poor people that he was always quoting Henry Wallace".[431] He was outspoken on racism, particularly towards blacks and Italians from early on. In November 1945 Sinatra was invited by the mayor of Gary, Indiana to try to settle a strike by white students of Froebel High School against the "Pro-Negro" policies of the new principal. Sinatra outraged the mayor with his remarks about how to address the problem, which he compared it to the racial policies of Nazism, and criticized the people involved in the dispute who had nothing to do with the school.[432] His comments, while praised by liberal publications, led to accusations by some that he was a Communist.[433] Sinatra responded by saying: "I don't like Communists, and I have nothing against any organization except the Knights of Columbus".[434] In the 1948 presidential election, Sinatra actively campaigned for President Harry S. Truman.[435] In 1952 and 1956, he also campaigned for Adlai Stevenson.[435]

Of all the U.S. Presidents he associated with during his career, he was closest to John F. Kennedy.[435] Sinatra often invited Kennedy to Hollywood and Las Vegas, and two would womanize and enjoy parties together. Kennedy enjoyed hearing inside gossip about the stars and their romances from him. [436] In 1960 Sinatra and his friends — Peter Lawford, Dean Martin, and Sammy Davis Jr. - actively campaigned for Kennedy throughout the United States;[435] A specially recorded version of "High Hopes" with lyrics praising Kennedy, frequently was played during the 1960 presidential election.[435] In January 1961 Sinatra and Peter Lawford organized the Inaugural Gala in Washington, DC, held on the evening before President Kennedy was sworn into office.[435] The event, featuring many notable entertainment figures, was an enormous success, raising a large amount of money for the Democratic Party.[437]

Sinatra's move toward the Republican party seems to have begun when he was snubbed by President Kennedy in favor of Bing Crosby,[438] a fellow singer and a Republican, for Kennedy's visit to Palm Springs, in 1962. Kennedy had planned to stay at Sinatra's home over the Easter holiday weekend, but decided to stay with Crosby because of Sinatra's alleged connections to organized crime.[y][438] Sinatra had invested a lot of his own money in upgrading the facilities at his home in anticipation of the President's visit, fitting it with a heliport and building a large guest house to seat 40 people.[440] Sinatra was fuming and "deeply humiliated" at being rejected, smashing up the concrete of the heliport himself with a sledgehammer.[441] He blamed Lawford and Bobby Kennedy for the decision, and created a rift between Lawford and the other Rat Pack members, cutting him out of subsequent films.[442] Yet Sinatra never said a bad word about Kennedy himself,[443] and despite the humiliation and change in political affiliation, he still mourned when Kennedy was assassinated.[435] According to his daughter Nancy, Sinatra learned of Kennedy's assassination while filming a scene of Robin and the 7 Hoods in Burbank.[435] Sinatra quickly finished filming the scene, returned to his Palm Springs home, and sobbed in his bedroom for three days.[435] When he learned that Kennedy's killer Lee Harvey Oswald had watched Suddenly just days before the assassination, he withdrew it from circulation, and it only became distributed again in the late 1980s.[444]

Political activities, 1970–94[edit]

Sinatra is awarded the Presidential Medal of Freedom by President Ronald Reagan

Sinatra remained a supporter of the Democratic Party until the early 1970s when he switched his allegiance to the Republican Party as the Democratic Party under George McGovern took a sharp turn to the left that was in conflict with his more traditional values.[445] The first sign of Sinatra's break from the Democratic Party came in 1970 when he endorsed Ronald Reagan for a second term as Governor of California;[435] Sinatra, however, remained a registered Democrat and encouraged Reagan to become more moderate.[435] In July 1972, after a lifetime of supporting Democratic presidential candidates, Sinatra announced he could not support the left-ward turn of the party and its candidate, George McGovern, and would therefore support Republican U.S. President Richard Nixon for re-election in the 1972 presidential election. His switch to the Republican Party was now official;[435] he even told his daughter, Tina, who had actively campaigned for Nixon's Democratic opponent George McGovern,[435] "the older you get, the more conservative you get."[435] Sinatra said he agreed with the Republican Party on most positions.[446] During Nixon's Presidency, Sinatra visited the White House on several occasions.[435]

In the 1980 presidential election, Sinatra supported Ronald Reagan and donated $4 million to Reagan's campaign.[447] He sponsored the initial fundraising campaign in the northeast, raising over $250,000 in Boston.[448] Sinatra referred to Reagan as "the proper man to be the President of the United States ... it's so screwed up now, we need someone to straighten it out."[449] Reagan's victory gave Sinatra his closest relationship with the White House since the early 1960s. Sinatra arranged Reagan's Presidential gala, as he had done for Kennedy 20 years previously.[450] In 1984, Sinatra returned to his birthplace in Hoboken, bringing with him President Reagan, who was in the midst of campaigning for the 1984 presidential election. Reagan had made Sinatra a fund-raising ambassador as part of the Republican National Committee's "Victory '84 Get-Out-The-Vote" (GOTV) drive.[451]

Racial activism[edit]

From his youth, Sinatra displayed sympathy for African Americans and worked both publicly and privately all his life to help them win equal rights. In 1947 he remarked: "We've got a hell of a way to go in this racial situation. As long as most white men think of a Negro as a Negro first and a man second, we're in trouble. I don't know why we can't grow up. It took us long enough to get past the stage where we were calling all Italians "wops" and "dagos", but if we don't stop this "nigger" thing, we just won't be around much longer." [266]

Sammy Davis, Jr. at a 1963 Civil Rights Convention

Sinatra played a major role in the desegregation of Nevada hotels and casinos in the 1950s and 1960s, often stepping in to demand apologies for a racist incident and abolishing of Jim Crow policies before he would fulfill his show contract. At the Sands in 1955, Sinatra noticed that he never saw Nat King Cole in the dining room, always eating his meals in solitude in his dressing room. When he asked his valet George to find out why, he learned that "Coloreds aren't allowed in the dining room at the Sands". Sinatra subsequently saw to it that if blacks weren't permitted to eat their meals in the dining room with everybody else he would see to it that all of the waiters and waitresses were fired, and invited Cole to dine with him the following evening.[452] Sinatra and Sammy Davis, Jr. were instrumental in bringing about a general change in policy. In 1961, an African-American couple entered the lobby of the hotel and were blocked by the security guard, witnessed by Sinatra and Davis. Sinatra told the guards that they were his guests and let them into the hotel. Sinatra subsequently swore profusely down the phone to Sands executive Carl Cohen at how ridiculous the situation was, and the following day, Davis approached Entratter and the hotel soon began hiring black waiters and busboys.[453] Sinatra's support for Sammy Davis, Jr., however, didn't stop the occasional racist jibe from him and the other Rat Pack members at concerts.[191]

On January 27, 1961, Sinatra played a benefit show at Carnegie Hall for Martin Luther King, Jr. and led his fellow Rat Pack members and Reprise label mates in boycotting hotels and casinos that refused entry to black patrons and performers. He often spoke from the stage on desegregation and repeatedly played benefits on behalf of Dr. King and his movement. According to his son, Frank Sinatra, Jr., King sat weeping in the audience at one of his father's concerts in 1963 as Sinatra sang Ol' Man River, a song from the musical Show Boat that is sung by an African-American stevedore. His well-known support for African-Americans was the subject of a piece in the Chicago Tribune by Laura S. Washington.[454] When he changed his political affiliations in 1970, Sinatra became less outspoken on racial issues.[266]

In 1981, Sinatra performed in Sun City, South Africa, at a time when he believed that Bophuthatswana was an independent country. He was heavily criticized for performing there, and the official from the National Congress of South Africa was quoted in saying "He is trying to pretend that he's going tin a separate state, which it is not. We don't recognize Bophuthatswana as a separate state of South Africa, and our policy is the same as if he agreed to perform in South Africa. He is saying that black people of South Africa should be living on 13% of the land.[265]


Sinatra's gravestone at Desert Memorial Park in Cathedral City, California

Kelly states that Sinatra "hated growing old", and that it frustrated him wearing a hearing aid, losing his hair and part of his memory. She claims that he prepared for his death in the 1990s by forcing gradually himself to say goodbye to loved ones.[283] When he avoided Dean Martin's funeral in 1995, some argued that it was due to a past disagreement involving the Rat Pack, but Sinatra did not want to be seen publicly breaking down at the loss. It also embarrassed him that there was a family feud over his $200 million estate in the years leading up to his death.[283]

Sinatra died by his wife's side at Cedars-Sinai Medical Center in Los Angeles on May 14, 1998, aged 82, after suffering a severe heart attack.[455][397] Sinatra had suffered from ill health for the last few years of his life, and had been frequently hospitalized for heart and breathing problems, high blood pressure, pneumonia and bladder cancer, as well as suffering from dementia.[456] He had made no public appearances following a heart attack in February 1997.[455] Sinatra's wife encouraged him to "fight" while attempts were made to stabilize him, and his final words were, "I'm losing."[457] Sinatra's daughter, Tina, later wrote that she and her sister, Nancy, had not been notified of their father's final hospitalization, and it was her belief that "the omission was deliberate. Barbara would be the grieving widow alone at her husband's side."[458] The night after Sinatra's death, the lights on the Empire State Building in New York City were turned blue. Also right after Sinatra's death, the lights on the Las Vegas Strip were dimmed in his honor, and the casinos stopped spinning for a minute.[459][397]

Sinatra's funeral was held at the Roman Catholic Church of the Good Shepherd in Beverly Hills, California, on May 20, 1998, with 400 mourners in attendance and thousands of fans outside.[460] Gregory Peck, Tony Bennett, and Sinatra's son, Frank, Jr. addressed the mourners, who included many notable people from film and entertainment.[457][460] Sinatra was buried with mementos from family members including cherry-flavored Life Savers, Tootsie Rolls, a bottle of Jack Daniel's, a pack of Camel cigarettes and a Zippo lighter, stuffed toys, and a dog biscuit, next to his parents in section B-8 of Desert Memorial Park in Cathedral City, California.[461][462] His close friends, Jilly Rizzo and Jimmy Van Heusen, are buried nearby. The words "The Best Is Yet to Come", plus "Beloved Husband & Father" are imprinted on Sinatra's grave marker.[463]

Honors and legacy[edit]

Frank Sinatra's television star on the Hollywood Walk of Fame, located on 1637 Vine Street

For Santopietro, Sinatra amassed "unprecedented power onscreen and off", and "seemed to exemplify the common man, an ethnic twentieth-century American male who reached the 'top of the heap', yet never forgot his roots". He argues that Sinatra created his own world, which he was able to dominate—his career was centred around power, perfecting the ability to capture an audience.[464]

The United States Postal Service issued a 42-cent postage stamp in honor of Sinatra in May 2008, commemorating the tenth anniversary of his death.[465][466] The United States Congress passed a resolution introduced by Representative Mary Bono Mack on May 20, 2008, designating May 13 as Frank Sinatra Day to honor his contributions to American culture.[467]

In Sinatra's native New Jersey, Hoboken's Frank Sinatra Park, the Hoboken Post Office,[466] and a residence hall at Montclair State University were named in his honor.[468] Other buildings named for Sinatra include the Frank Sinatra School of the Arts in Astoria, Queens, the Frank Sinatra International Student Center at Israel's Hebrew University in Jerusalem dedicated in 1978,[469] and the Frank Sinatra Hall at the USC School of Cinematic Arts in Los Angeles, California, dedicated in 2002.[470] Wynn Resorts' Encore Las Vegas resort features a restaurant dedicated to Sinatra which opened in 2008.[471] Items of memorabilia from Sinatra's life and career are displayed at USC's Frank Sinatra Hall and Wynn Resort's Sinatra restaurant.[470][471] Near the Las Vegas Strip is a road named Frank Sinatra Drive in his honor.[472]

Sinatra has three stars on the Hollywood Walk of Fame, for his work in film and music on the east and west sides of the 1600 block of Vine Street respectively, and his work in television on the south side of the 6500 block of Hollywood Boulevard.[473]

Sinatra received three honorary degrees during his lifetime. In May 1976, Frank Sinatra was invited to speak at the University of Nevada, Las Vegas (UNLV) graduation commencement held at Sam Boyd Stadium. It was at this commencement that he was bestowed an Honorary Doctorate litterarum humanarum by the university.[474] During his speech, Sinatra noted that his education had come from "the school of hard knocks" and was suitably touched by the award. He went on to describe that "this is the first educational degree I have ever held in my hand. I will never forget what you have done for me today".[475] A few years later in 1984 and 1985, Sinatra also received an Honorary Doctorate of Fine Arts from Loyola Marymount University as well as an Honorary Doctorate of Engineering from the Stevens Institute of Technology.[476][477]

Film and television portrayals[edit]

Sinatra has been portrayed on numerous occasions in film and on television. A television miniseries based on Sinatra's life, titled Sinatra, was aired by CBS in 1992. Sinatra was directed by James Steven Sadwith, who won an Emmy award for Outstanding Individual Achievement in Directing for a Miniseries or a Special, and starred Philip Casnoff as Sinatra. Sinatra was written by Abby Mann and Philip Mastrosimone, and produced by Sinatra's daughter, Tina.[478]

Sinatra has subsequently been portrayed on screen by Ray Liotta (The Rat Pack, 1998), James Russo (Stealing Sinatra, 2003), Dennis Hopper (The Night We Called It a Day, 2003), Chris Diamantopoulos (The Kennedys, 2011), and Robert Knepper (My Way, 2012), and spoofed by Joe Piscopo and Phil Hartman on Saturday Night Live. A biographical film directed by Martin Scorsese has long been in production.[479] A 1998 episode of the BBC documentary series Arena, The Voice of the Century, focused on Sinatra.[480] Alex Gibney directed a four part biographical series on Sinatra, All or Nothing At All, for HBO in 2015.[481]




Frank Sinatra co-wrote the following songs:

See also[edit]



  1. ^ Kaplan claims that Dolly earned $50 per procedure, and became known as "Hatpin Dolly".[28] She was reportedly arrested six or seven times and convicted twice for providing illegal abortions,[29][30] the first of which was in 1937.[31]
  2. ^ Sinatra's loss of employment at the newspaper led to a life-long rift with Garrick. Dolly said of it: "My son is like me. You cross him, he never forgets".[44]
  3. ^ Kelley claims that the jealousy exhibited by the group members often led to brawls in which they would beat the small, skinny young Sinatra.[61]
  4. ^ Kelley claims that Dolly bought the system in guilt after Sinatra had been rejected by an Irish Catholic church for arranging the orchestra, due to her abortion business.[65]
  5. ^ In March 1939, Sinatra made his first recording of a song called "Our Love". Saxophone player Frank Mane knew Sinatra from Jersey City radio station WAAT where both performed on live broadcasts. Hoping for a job with Clyde Lucas, Mane had arranged to make an audition record with a 10 piece band at a New York recording studio. When Mane mentioned this to Sinatra, he asked Mane if he could go along and sing with the band. After recording four songs with the band to showcase his talents on the saxophone. Mane found there was time left on the session and let Sinatra record the song, "Our Love"; it was Sinatra's first solo in a recording studio. Mane wrote "Frank Sinatra" on the record label and kept the recording in a drawer through the years. Mane died in 1998, only months after Sinatra's death; in 2006, Mane's widow offered the recording for sale through Gurnsey's auction house in New York.[70]
  6. ^ the vocalist, not to be confused with the comedian Jack E. Leonard
  7. ^ Sinatra's lawyer, Henry Jaffe, met with Dorsey's lawyer N. Joseph Ross in Los Angeles in August 1943. In the words of Kelley: "In the end, MCA, an agency representing Dorsey and courting Sinatra, made Dorsey a $60,000 offer that he accepted. To obtain Frank as a client, the agency paid Dorsey $35,000 while Sinatra paid $25,000, which he borrowed from Manie Sacks as an advance against his royalties from Columbia Records. MCA agreed that until 1948 it would split its commissions on Sinatra with GAC, the agency that Frank had signed with when he left the Dorsey band."[92] However, during a 1979 concert at the Universal Amphitheatre in Los Angeles, Sinatra claimed that it took him years to escape the contract, and that Dorsey had cost him seven million dollars.[93]
  8. ^ According to Kelley, Budd Granoff had stated that on the night before Evans's death, he had been highly distraught upon learning of Sinatra's intent to marry Ava Gardner, and had been quoted as saying "he's making a terrible, terrible mistake".[137]
  9. ^ Producer Irving Mansfield described Sinatra as being obsessed with the thought that his wife, Ava Gardner, was having an affair with her former husband, Artie Shaw. He often started shouting about this on the set of the television show when he phoned his home and could not reach Gardner. Mansfield had to communicate with Sinatra through the entourage that always accompanied him to CBS. Sinatra was always late to work and did not care to spend any time at rehearsal; he blamed all those connected with the program for the poor ratings it received. Mansfield was at his wits' end with Sinatra and his television show and quit the program. When Mansfield asked Sinatra to repeat a segment during the last rehearsal he was responsible for, Sinatra told the producer He did not have time to do it again and did not care what Mansfield liked or did not like. Manfield responded by telling him he was a man of great talent but a failure as a person. Sinatra became angry and fired the producer; Mansfield replied that he was too late, as he had resigned that morning.[146]
  10. ^ Miller tried to offset Sinatra's declining record sales by introducing "gimmicky novel tunes" into the singer's repertoire such as "Mama Will Bark" to appeal to younger audiences.[151][152] "Mama Will Bark" is often cited as the worst of Sinatra's career. Miller thought he would try this novelty approach for Sinatra because he felt the singer's "great records" weren't selling.[153] Initially, Sinatra went along with this approach, but eventually he came to resent Miller for the poor quality of material he was being offered.[154]
  11. ^ Kelley claims that Sinatra bought a two percent share in the hotel for $54,000. At one point the share reached nine percent.[160] He was reportedly ordered to sell his interest in the Sands in 1963, due to his association with mobster Sam Giancana.[161]
  12. ^ Sinatra was not very enthusiastic about the song initially. His friend, Jimmy Van Heusen, convinced him that the song would be a success.[177]
  13. ^ Young at Heart was produced by Day's husband at the time, Marty Melcher. Sinatra had an intense dislike for Melcher, calling him a "heel and a fucking creep" to his face. Sinatra disliked Melcher enough to insist that he would not work on the set if Melcher was anywhere on the Warner lot. The feud grew worse when Melcher suggested that Day sing Young at Heart as the film's title song. Sinatra's recording of the song was already a hit. Day conceded that she did not care whose voice was heard singing the film's title song. Because of the rift, the Young at Heart soundtrack album contains all the songs heard in the film but the title Young at Heart. Sinatra's hit recording is heard at the beginning and end of the film.[181]
  14. ^ Presley had responded to the criticism: "... [Sinatra] is a great success and a fine actor, but I think he shouldn't have said it ... [rock and roll] is a trend, just the same as he faced when he started years ago."[200]
  15. ^ Sinatra came to his last engagement at the Sands with the expectation that new owner Howard Hughes would relieve him of his ownership in the Cal Neva Lodge & Casino in Lake Tahoe. Sinatra had long wanted to sell his interest in the property and reasoned that since he was an asset to the Sands' business, Hughes would buy his Cal-Neva shares in the interest of keeping the star happy. Hughes declined to buy Sinatra's shares.[220]
  16. ^ Sinatra also destroyed the Sands penthouse apartment he was staying in during his engagement there.[223]
  17. ^ Horne developed vocal problems and Sinatra, committed to other engagements, could not wait to record.
  18. ^ Mortimer wrote a series of articles over at least two and a half years in which he described the alleged exploits of Sinatra and the mob, and attempted to destroy his career by questioning the intelligence of the bobbysoxers who would worship a man who socialized with gangsters. Kelley claims that his articles grew so offensive that Sinatra pounced on him outside Ciro's and punched him behind the left ear in response to an insult in which he was called a "dago", threatening to kill him, and had to pinned down to the ground by friends. Sinatra was taken to court, and according to Kelley, Mortimer received Mafia threats to drop the case or lose his life.[303]
  19. ^ Hughes and Sinatra had both courted Ava Gardner. Hughes was envious because Gardner did not return his interest and had married Sinatra. For his part, Sinatra believed that Gardner and Hughes had a previous relationship, though Gardner denied this. Hughes, who was the owner of RKO Pictures, intensified Sinatra's wrath against him when he was working on the 1951 film Double Dynamite. Hughes demoted Sinatra's billing in the film to third and eventually barred him from the RKO lot.[311]
  20. ^ Sinatra successfully later sued a BBC interviewer who claimed that he'd used his Mafia connections to get the part.[320]
  21. ^ Sinatra only accepted the role as he wanted to be closer to Ava Gardner while she was filming The Sun Also Rises in Europe, due to marriage problems.[346] Sinatra insisted on staying at the Hotel Castellana in Madrid, rather than on location with the rest of the cast, and when Kramer failed to pay $5000 to send his Thunderbird from Los Angeles to Madrid, he had to hire a $15,000 Mercedes and a chauffeur especially for him.[347]
  22. ^ The film was later made by Stanley Kubrick in 1971 and is now considered to be one of the greatest films of all time.[369][370]
  23. ^ Kelley states that this was covered up by his representatives who told the press he had been admitted to hospital, suffering from "complete physical exhaustion, severe loss of weight, and a tremendous amount of emotional strain", and that he had simply had an accident with a broken glass.[387]
  24. ^ Sinatra always dressed immaculately, both in his professional and private life. He believed that as he was the best, he had to give his best to the audience, and would wear expensive custom-tailored tuxedos on stage as a sign of respect and to look important.[399]
  25. ^ At the time, President Kennedy's brother, Attorney General Robert F. Kennedy, was intensifying his own investigations into organized crime figures such as Chicago mob boss Sam Giancana, who had earlier stayed at Sinatra's home. Kennedy was strongly advised by Henry Petersen, a senior official of the Justice Department, to avoid staying with Sinatra, stating: "Sinatra has a long and wide association with hoodlums and gangsters which seems to be continuing. The nature of Sinatra's work may, on occasion, bring him into contact with underworld figures, but this cannot account for his friendship and/or financial involvement with people such as Joe and Rocco Fischetti, cousins of Al Capone; Paul Emilio D'Amato, John Formosa, and Sam Giancana, all of whom are on our list of racketeers. No other entertainer appears to be mentioned nearly so frequently with racketeers".[439]


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