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]

Hoboken, New Jersey, early 20th century

Francis Albert Sinatra was born on December 12, 1915, in an upstairs tenement in Hoboken, New Jersey.[a] He was the only child of Italian immigrants Natalina "Dolly" Garaventa, the daughter of a lithographer from Genoa,[9] and Antonino Martino "Marty" Sinatra, from Catania, Sicily.[10][11][12] The couple had eloped on Valentine's Day, 1913 and married in a civil ceremony in Jersey City, New Jersey, but later completed a sanctified marriage in the Church.[13] Sinatra was raised Roman Catholic.[14]

Sinatra weighed 13.5 pounds (6.1 kg) at birth[15] 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 that remained for life.[16][17] Due to his injuries at birth, his baptism was delayed for several months.[15] 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.[18] As a result, some children later called him "Scarface"; he later said he wanted to physically assault the doctor who had delivered him.[19] Sinatra was raised Roman Catholic,[20][21]

When Sinatra's mother was a child, her pretty face earned her the nickname "Dolly". As an adult, she stood less than five feet tall and weighed approximately 90 pounds.[22] She was the daughter of a lithographer.[9] Born in Genoa in northern Italy, she was brought to the United States when she was two months old.[23] Energetic and with a gift for languages, she used her knowledge of Italian dialects and fluent English to translate for immigrants during court proceedings, particularly those pertaining to requests for citizenship. This earned her the respect of local politicians, who made her a Democratic ward leader.[13] She became influential in Hoboken and in local Democratic Party circles, [24] was the first immigrant woman to lead her local third ward, and reliably delivered as many as six hundred votes for Democratic candidates.[25] In 1919, she chained herself to city hall in support of the Women's suffrage movement. She also worked as a midwife, earning $50 for each delivery, a fair amount of money at the time. These activities kept Dolly away from home during much of her son's childhood.[22] Sinatra biographer Kitty Kelley claims that Dolly also ran an illegal abortion service that catered to Italian Catholic girls.[26][b]

Immigrants arriving at Ellis Island, c. 1902

Sinatra's father, Antonino was a small, blue-eyed, ruddy-complexioned man[23] born in Catania, Sicily.[10] He arrived at Ellis Island with his mother and sisters in 1903, when they joined his father, Francesco Sinatra, who had immigrated to the US in 1900.[30] Antonino was a bantamweight boxer who fought under the name Marty O'Brien.[10] He retired from boxing in 1926, after having broken both wrists, and later found work on the docks as a boilermaker, but was soon laid off due to problems with asthma.[31] He served with the Hoboken Fire Department for 24 years, working his way up to Captain.[32] Sinatra's biographer James Kaplan stated that Marty never learned to read.[30] 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.[33] Other family members had minor clashes with the law; Sinatra's father and uncles had been arrested for assorted minor offenses.[34]

Sinatra spent some of his childhood at his parent's tavern in Hoboken, working on his homework and occasionally singing a song on top of the player piano for spare change.[35][36] 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."[37] Though Prohibition of alcohol became law in the United States, Dolly and Marty were allowed to operate openly by local officials who refused to enforce Prohibition.[35] Kaplan notes the possibility that the Sinatras procured their liquor from members of the Mafia. They purchased the bar, which they named Marty O'Brien's, with money they borrowed from Dolly's parents. When they were busy with the tavern, Sinatra was watched by relatives and sometimes a Jewish neighbor named Mrs. Goldberg, who taught him Yiddish.[38] Sinatra enrolled at A. J. Demarest High School in 1931, where he arranged bands for school dances.[39] He left without graduating, having attended only 47 days before being expelled for "general rowdiness".[40][41] Sinatra's father was particularly disappointed with his son, hoping that he would make it to college.[42] To please his mother, Sinatra enrolled at Drake Business School, but departed after 11 months.[39] Dolly found work for him as a delivery boy at the Jersey Observer newspaper, where his godfather Frank Garrick worked,[c] 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.[44] Sinatra also worked as a riveter at the Tietjen and Lang shipyard.[45] According to Kaplan, Dolly doted on her son, but she also abused him when he angered her, hitting him with small bat she kept at Marty O'Brien's.[46] 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.[42]

Sinatra developed an interest in music, particularly big band jazz, at a young age.[40] During his early teenage years Sinatra forced himself to develop his voice as he was under wanting to "make something of himself".[37] During the Great Depression, Dolly provided money to her son for outings with friends and to buy expensive clothes, and neighbors described him as the "best-dressed kid in the neighborhood".[47] He earned pocket money by singing on street corners.[48] Dolly was not enthusiastic at the idea of her son becoming a singer.[49] When Sinatra was 11 years old, he would sing along with piano player in his parents' bar. It was then Dolly realized her son had the potential to become a singer.[49] He listened to Gene Austin, Rudy Vallée, Russ Colombo and Bob Eberly, and "idolized" Bing Crosby.[37] Sinatra's maternal uncle, Domenico, gave him a ukulele for his 15th birthday, and he began performing at family gatherings.[39] 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.[50] In New York, Sinatra found jobs singing for his supper or for cigarettes.[39] To improve his speech, he began taking elocution lessons for a dollar each from vocal coach John Quinlan, who was one of the first people to notice his impressive vocal range, later saying, "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".[51]

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, but he learned music by ear and never learned to read music.[52][53] 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", admitting they only took him on board because he owned a car and could chauffeur the group around. Sinatra soon learned they were auditioning for the Major Bowes Amateur Hour show, and "begged" the group to let him in on the act.[54] With Sinatra, the group became known as the Hoboken Four, and they sufficiently impressed Edward Bowes that he invited them to appear on his show. They each earned $12.50 for the appearance,[55] 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.[56] 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.[57][d] He spent lavishly on stylish pin-striped suits and other clothing, aided by friend Nick Sevano, who worked at De Santos tailors in Hoboken.[58] He later admitted that clothing made him feel wealthy and important, bolstering his ego.[59] 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".[42] In early 1936, Dolly paid for a $65 portable public-address system that her son used for performing in public.[60]

Harry James in 1942

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.[61][62] 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".[63] Fellow musicians began to resent his cocksure attitude and mocked him for having little talent, to which Sinatra would flare up, angrily cursing and swearing at the others.[64] In March 1939, Sinatra made his first solo studio recording, a song called "Our Love". Saxophone player Frank Mane knew Sinatra from Jersey City radio station WAAT where both performed on live broadcasts. Mane had arranged to make an audition record at a New York recording studio and let Sinatra record the song; it was Sinatra's first solo in a recording studio.[65][e]

In June 1939, bandleader Harry James had an engagement at the Paramount Theatre in New York. One evening after his show, he heard Sinatra sing on "Dance Parade". The announcer did not identify the singer, but 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. James 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] Neither 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 the issue.[68][69]

It was with the James band that Sinatra released his first commercial record "From the Bottom of My Heart" in July 1939.[f] 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.[70]

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 Simon to give Sinatra a good write-up, because he "wants it more than anybody I've ever seen".[71] 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..."[72] 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".[72]

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, he had "cut out completely—dead" after becoming starstruck.[73] Dorsey asked Sinatra to join his band for $125 a week as a replacement for Jack Leonard,[g] who had recently left to launch a solo career. This meeting was a turning point in Sinatra's career;[74] 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 released Sinatra from his contract.[75] Sinatra acknowledged his debt to James throughout his life, and upon hearing of James' death in 1983, stated: "he is the one that made it all possible."[76]

"The only two people I've ever been afraid of are my mother and Tommy Dorsey".[77]


On January 26, 1940, Sinatra made his first public appearance with the Dorsey band at the Coronado Theatre in Rockford, Illinois.[78] 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".[79] Sinatra’s first song for Dorsey was "Stardust", and in the first four bars of the song, Jo Stafford, then a vocalist with The Pied Pipers, later said she suspected that Sinatra would become a star.[80]

Dorsey was a major influence on Sinatra and became a father figure. Sinatra copied Dorsey's 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 became the godfather of Sinatra's daughter Nancy in June 1940.[81] Dorsey advised Sinatra to listen to Bing Crosby, the only singer Dorsey thought that Sinatra should emulate.[82] According to Kelley, Sinatra and drummer Buddy Rich became bitter rivals, as both were 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 filled with water and ice at Rich's head. 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

In his first year with Dorsey, Sinatra released over forty songs, with "I'll Never Smile Again" topping the charts for twelve weeks beginning in mid-July.[84] and making Sinatra a star.[58] 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, Sinatra pushed Dorsey to allow Sinatra 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" at a Bluebird recording session, with Axel Stordahl as arranger and conductor.[86][87] 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".[87]

Sinatra with arranger Axel Stordahl in the 1940s

Sinatra believed he needed to go solo,[88] and later said "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".[89] But, he was hampered by his contract, which gave Dorsey 43% of Sinatra's lifetime earnings in the entertainment industry.[89] A legal battle ensued, eventually settled in August 1943.[90][h] 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.[92] The incident started rumors of Sinatra's involvement with the Mafia, and was fictionalized in the book and movie The Godfather.[93]

On September 3, 1942, Dorsey bid farewell to Sinatra, reportedly saying as Sinatra left, "I hope you fall on your ass",[89] and replaced Sinatra with singer Dick Haymes.[75] Dorsey and Sinatra, who had been very close, never patched up their differences before Dorsey's 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 persuaded Stordahl to leave Dorsey with him and become his personal arranger, offering him $650 a month, five times the salary of Dorsey.[95]

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.[96] 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.[97] The phenomenon became officially known as "Sinatramania" after his "legendary opening" at the Paramount Theatre in New York on December 30, 1942.[89] 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."[98] 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.[99] 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.[100] 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.[101] 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?".[102] 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.[103]

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.[76] 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.[104] 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.[105] 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,[106] 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.[107] 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.[108] A successful concert in the Wedgewood Room of the prestigious Waldorf-Astoria New York secured his popularity in New York high society.[109] 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.[110] 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".[111]

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".[112] 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.[113] Briefly, there were rumors reported by columnist Walter Winchell,[114] that Sinatra paid $40,000 to avoid the service – but the FBI found this to be without merit.[115][116] 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.[117]

Towards the end of the war, Sinatra entertained the troops during several successful overseas USO tours with comedian Phil Silvers.[118] During one trip to Rome he met the Pope, who asked him if he was an operatic tenor.[119] Sinatra worked frequently with the popular Andrews Sisters, both on radio in the 1940s, appearing as guests on each other's shows,[120] as well as on many USO shows broadcast to troops via the Armed Forces Radio Service (AFRS).[121] He appeared as a special guest in the sisters' ABC Eight-to-the-Bar Ranch series,[122] while the trio in turn guested on his Songs by Sinatra series on CBS.[123]

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.[111]

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".[124] Summers and Swan note that despite being heavily involved in political activity in 1945 and 1946, in those two years Sinatra "sang on 160 radio shows, completed thirty-six recording sessions, and made four movies". By 1946 he was performing on stage up to 45 times a week, singing up to 100 songs daily, and earned $93,000 once in on week.[125] Sinatra released "Oh! What it Seemed to Be", "Day by Day", "They Say It's Wonderful", "Five Minutes More" and "The Coffee Song" as singles,[126] and launched his first album, The Voice of Frank Sinatra.[127] He was soon selling ten million records a year.[128] 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.[129]

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".[130] "Mam'selle", composed by Edmund Goulding with lyrics by Mack Gordon for the film The Razor's Edge (1946),[131] was released a single.[126] Sinatra had competition; versions by Art Lund, Dick Haymes, Dennis Day, and The Pied Pipers also reached the top ten of the Billboard charts.[132]

In 1948, when Sinatra featured as a priest in The Miracle of the Bells, due to press negativity surrounding his alleged Mafia connections at the time, Evans announced to the public that Sinatra would donate his $100,000 in wages from the film to the church.[133] He was involved in a violent incident with journalist Lee Mortimer, who 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, 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.[134] Sinatra's third album, Christmas Songs by Sinatra, was originally released in 1948 as a 78 rpm album set (C-167) and a 10" LP record featuring a collection of holiday songs. A compilation album was released in 1994 including the songs on the original release and a collection of Christmas songs from the Columbia years.[citation needed]

Sinatra in a Lucky Strike advert

Sinatra was the star of various radio shows of his own on NBC and CBS from the early 1940s to the mid 1950s. Sinatra hired arranger Axel Stordahl away from Tommy Dorsey before he began his first radio program in 1942 and kept Stordahl with him for all of his radio work.[135] Your Hit Parade was a popular weekly radio and television program from 1935 to 1958. Sponsored by American Tobacco Company’s Lucky Strike brand of cigarettes, the show featured the top ten songs of each week.[136] Sinatra had two stints as a regular member of the show’s cast; his first was from 1943 to 1945[137] While Sinatra left the program in 1945, he returned in 1946 and was paired with a new girl singer named Doris Day.[138] Sinatra left the program permanently on May 28, 1949.[139] Starting in September 1949, the BBD&O advertising agency produced a radio series starring Sinatra for Lucky Strike called "Light Up Time" – some 176 15-minute shows which featured Frank and Dorothy Kirsten singing – which lasted through to May 1950.[140][141]

Sinatra's Frankly Sentimental (1949), a compilation of eight recordings between 1946 and 1947,[142] was panned by Downbeat, who commented that "for all his talent, it seldom comes to life".[143] He released "The Huckle Buck" as a single, which made the top ten,[144] his last single release under the Columbia label.[126]

Sinatra's last two albums with Columbia, Dedicated to You and Sing and Dance with Frank Sinatra, were released in 1950. The original Sing and Dance with Frank Sinatra album, all arranged and conducted by George Siravo and his orchestra, except for track four, was released as a 10-inch 33 1/3-rpm LP and 78-rpm album set on October 16, 1950.[citation needed] The 7-inch 45-rpm EP and EP box sets of the album were released in October 1952,[citation needed] and Sinatra would later feature a number of the album's songs, including "Lover", "It's Only a Paper Moon", "It All Depends on You", on his 1961 Capitol release, Sinatra's Swingin' Session!!!.[citation needed]

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).[145] 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.[143] Cementing the low of his career was the death of publicist George Evans from a heart attack in January 1950 at just 48.[i] 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".[146]

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.[147] 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.[148] Sinatra was forced to cancel his remaining Copa performances and take a two week vacation with Gardner on the Spanish Mediterranean coast, to recover.[149] Evans once noted that whenever Sinatra suffered from a bad throat and loss of voice it was always due to emotional tension which "absolutely destroyed him".[150]

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.[151] Rejected by Hollywood, he turned to Las Vegas and made his debut at the Desert Inn in September 1951,[152] becoming one of its pioneer entertainers.[153] He also began singing at the Riverside Hotel in Reno, Nevada.[154] 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.[152] 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".[155]

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.[j] 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".[157]

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.[158] At the Desert Inn in Las Vegas he performed to half-filled houses of wildcatters and ranchers.[159] At a concert at Chez Paree in Chicago, only 150 people in a 1,200-seat capacity venue turned up to see him.[160] 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.[158][k] 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.[163] 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.[165] Columbia and MCA dropped him later that year.[166] Journalist Burt Boyer observed, "Sinatra had had it. It was sad. From the top to the bottom in one horrible lesson."[158] Sinatra would claim that it was he that quit Columbia, because of the "corny things — gimmicks" that Miller wanted him to do.[167]

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

Nelson Riddle, Sinatra's album arranger for Capitol Records

Sinatra's Academy Award for Best Supporting Actor win for From Here to Eternity in 1953 marked the beginning of a remarkable career revival.[168] He 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.[169] 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".[170] 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 [Gardner] 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".[171] 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.[172] 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.[173]

On October 4, 1953, Sinatra made his first performance at the Sands Hotel and Casino,[174] 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.[175] Sinatra typically performed there three times a year, and later acquired a share in the hotel.[l][178] 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.[179]

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".[180]

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".[181] 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.[182] 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",[182] which became staples of his later concerts.[183][42] 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".[184] 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.[185] That year he was also named "Top Male Vocalist" by Billboard, Down Beat and Metronome.[185][186][187] 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.[188][189][190][m] 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.[191] The Young at Heart album released by Day and Sinatra did not include the title song, which Sinatra recorded prior to his film work.[192][n] Sinatra also recorded a version of the song "Three Coins in the Fountain", a "powerful ballad" which was released as a single,[193] written by Jule Styne and Sammy Cahn for the Academy Award-nominated film of that year of the same name.[194]

In 1955 Sinatra released In the Wee Small Hours, his first 12" LP,[195] 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.[196] Riddle noted that Sinatra took "particular delight" in singing "The Lady is a Tramp", commenting that he "always sang that song with a certain amount of salaciousness", making "cue tricks" with the lyrics.[197] Also in 1956, Sinatra sang at Democrat convention, and performed with The Dorsey Brothers for a week soon afterwards at the Paramount Theatre.[198] His February 1956 recording sessions inaugurated the studios at the Capitol Records Building[199] 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.[200]

Dean Martin and Frank Sinatra in 1958

In 1957, Sinatra released Where Are You? (1957) – his first album in stereo, with Gordon Jenkins,[201] and Come Fly With Me (1957). On June 9, 1957, he performed in a 62 minute concert conducted by Riddle at the Seattle Civic Auditorium,[202] his first appearance in Seattle since 1935.[183] 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.[203] 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.[204] 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".[205]

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.[206] 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.[207] 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.[208]

In 1960, Nice 'n' Easy topped Billboard‍ '​s chart and won critical plaudits.[209][210] 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."[211][o] 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").[213]

Reprise years (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.[214] 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.[215] On September 11 and 12, 1961, Sinatra recorded his final songs for Capitol.[216]

In 1962, Sinatra and Count Basie collaborated for the album Sinatra-Basie.[217] 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.[218] Also that year, 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.[219] 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.[220] In 1964 the song "My Kind of Town" was nominated for the Academy Award for Best Original Song.[221] That year, when Bing Crosby joined the Reprise label, he stated: "Sinatra is a King. He's a very sharp operator, a keen record chief and has a keen appreciation of what the public wants. I'm happy to be associated with him after all these years".[222] Sinatra increasingly became involved in charitable pursuits in this period, and in July 1964 he was present for the dedication of the Frank Sinatra International Youth Center for Arab and Jewish children.[223]

Sinatra's phenomenal success in 1965, coinciding with his 50th birthday, prompted Billboard to proclaim that he may have reached the "peak of his eminence".[224] 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.[225] The album September of My Years, which including songs such as Van Heusen's and Cahn's "The September of My Years" and "It Gets Lonely Early" was released September 1965, and went on to win the Grammy Award for best album of the year.[226] One of the album's singles, "It Was a Very Good Year", won the Grammy Award for Best Vocal Performance, Male.[227] A career anthology, A Man and His Music, followed in November, winning Album of the Year at the Grammys the following year. A CBS News special about the singer's 50th birthday, Frank Sinatra: A Man and His Music, was broadcast on November 16, 1965, and garnered both an Emmy award and a Peabody Award.[228]

The Sands Hotel and Casino in 1959.

In 1966 Sinatra released That's Life, with both the single of "That's Life" and album becoming Top Ten hits in the US on Billboard's pop charts.[229] Strangers in the Night went on to top the Billboard and UK pop singles charts,[230][231] winning the award for Record of the Year at the Grammys.[232] 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.[233] 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.[234] 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.[235][p] Fuming, Sinatra began what The Los Angeles Times describes as a "weekend-long tirade" against the "hotel's management, employees and security forces",[237] during which there was a fight with Sands executive Carl Cohen, during which Sinatra lost two teeth.[238] As a result, Sinatra never performed at the Sands again while Hughes owned it, and began performing at Caesars Palace.[239]

Sinatra started 1967 with a series of recording sessions with Antônio Carlos Jobim. He recorded one of his most famous collaborations with Jobim, releasing the album Francis Albert Sinatra & Antonio Carlos Jobim, which was nominated for the Grammy Award for Album of the Year. It was one of the best-selling albums of the year, behind the Beatles's Sgt. Pepper's Lonely Hearts Club Band.[240] 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.[241] Also in 1967, a duet with daughter Nancy, "Somethin' Stupid", topped the Billboard pop and UK singles charts.[230][242] In December, Sinatra collaborated with Duke Ellington on the album Francis A. & Edward K..[243]

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.[244]

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.[245] "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.[246]

"Retirement" and return (1970-81)[edit]

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.[247] 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.[248] Watertown was one of the only recording sessions having Sinatra sing against pre-recorded tracks instead of a live orchestra.[249] On November 2, 1970, Sinatra recorded the last songs for Reprise Records before his self-imposed retirement.[250] One of the songs recorded during the session, "The Game is Over", was written by John Denver.[251]

Caesars Palace in 1970, where Sinatra performed from 1967-1970 and 1973 onwards

Sinatra was involved in another Las Vegas casino dispute while playing high stakes baccarat at Caesars Palace in the early morning hours of September 6, 1970.[q] When Sinatra began shouting, hotel executive Sanford Waterman came to talk with him. Witnesses to the incident said the two men both made threats, with Waterman producing a gun and pointing it at Sinatra. Sinatra left the casino after Waterman pointed the gun at him. Sinatra, who had begun an engagement at Caesars just days before the incident, returned to his Palm Springs home without fulfilling the rest of his three week engagement there. Waterman was booked on a charge of assault with a deadly weapon, but was released without bail.[253] The local district attorney's office declined to file charges against Waterman for pulling the gun, stating that Sinatra had refused to make a statement regarding the incident.[254]

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".[255] 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.[256]

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.[248] The album, arranged by Gordon Jenkins and Don Costa,[257] was a success, reaching number 13 on Billboard and number 12 in the UK.[258][259] 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.[260]

The following January, Sinatra returned to Las Vegas, performing at Caesars Palace despite previously vowing to perform there again.[261] 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.[262]

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.[263][264] The following August, Sinatra held several consecutive concerts at Lake Tahoe together with the newly-risen singer John Denver,[265][266] who became a frequent collaborator.[267] Denver later appeared as a guest in the Sinatra and Friends ABC-TV Special, singing "September Song" as a duet.[268] Sinatra covered the John Denver hits "My Sweet Lady" and "Leaving on a Jet Plane", arranged for him by Eumir Deodato.[269] 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.[270]

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.[271] Sinatra performed for the "Jerry Lewis MDA Telethon" that afternoon and before he performed he brought Martin out on stage.[272] He released an album that year, The Nearness of You.[273] 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.[274] 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.[275][276]

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.[277] The album garnered six Grammy nominations – winning for best liner notes – and peaked at number 17 on Billboard's album chart,[277] while spawning yet another song that would become a signature tune, "Theme from New York, New York",[278] 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).[279]

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".[280] 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.[281]

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".[282] 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.[283]

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".[284] 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.[285] 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.[286] 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.[287] 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.[288] He was forced to drop the case on September 19, 1984, with several leading newspapers expressing concerns about his views on censorship.[289]

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.[290] The album was a substitute for another Jones project, an album of duets with Lena Horne, which had to be abandoned.[291][r]

In 1987, Sinatra made a guest appearance opposite Tom Selleck in "Magnum, P.I.", playing a retired policeman who teams up with Selleck to find his granddaughter's murderer. Shot in January 1987, the episode aired on CBS on February 25.[292] 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.[293]

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.[294] 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.[17] 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.[17]

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.[295] His final public concerts were held in Fukuoka Dome in Japan on December 19–20, 1994.[296] 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.[297] Esquire reported of the show that Sinatra was "clear, tough, on the money" and "in absolute control".[298] 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".[297]

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?"[299] 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.[300]

In 1995, to mark Sinatra's 80th birthday, the Empire State Building glowed blue.[301] 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.[302] 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.[303] In recognition of his many years of association with Las Vegas, Frank Sinatra was elected to the Gaming Hall of Fame in 1997.[304]

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.[305] 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.[306] 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.[307] 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".[308] The following year he was given his leading roles in Higher and Higher[309][310] and Step Lively[311] for RKO Pictures.

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

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.[312][313] A major success,[314] 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.[315] Sinatra expressed "lifelong gratitude" to Kelly for tutoring him in acting and dancing and stated that he was instrumental in overcoming his doubts.[316] In 1946, Sinatra featured in a ensemble cast which included Robert Walker, Judy Garland and Lena Horne in the commercially successful Till the Clouds Roll By, a Technicolor musical biopic of Jerome Kern, directed Richard Whorf.[317][318]

In 1949, 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.[319] 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.[320] Both Double Dynamite (1951), an RKO Irving Cummings comedy produced by Howard Hughes,[321] and Joseph Pevney's Meet Danny Wilson (1952) failed to make an impression.[322][323] The New York World Telegram and Sun ran the headline "Gone on Frankie in '42; Gone in '52".[324]

Rebirth of career and acclaim (1953-59)[edit]

Sinatra as Maggio in From Here to Eternity (1953)

Fred Zinnemann's From Here to Eternity 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.[325] 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.[326] [s] 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".[328] 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.[329] 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".[330]

Sinatra in Suddenly (1954)

In 1954 Sinatra starred opposite Doris Day in the musical film Young at Heart,[331] 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",[332] 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).[333][t] 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.[335] Sinatra also featured alongside Debbie Reynolds in The Tender Trap,[336] 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.[337][338] Later in the year he was nominated for a BAFTA Award for Best Actor in a Leading Role for his role as hospital orderly in Stanley Kramer's debut picture, Not as a Stranger.[339][340] During production, Sinatra got drunk with Robert Mitchum and Broderick Crawford and trashed Kramer's dressing room.[341] Kramer vowed to never hire Sinatra again at the time, and later regretted casting him as a Spanish guerrilla leader in The Pride and the Passion (1957), a problematic production in Spain.[342] [343]

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

In 1956 Sinatra featured alongside Bing Crosby and Grace Kelly in High Society for MGM, earning a reported $250,000 for the picture.[344] 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.[345] In 1957, Sinatra starred opposite Rita Hayworth and Kim Novak in George Sidney's Pal Joey, for which he won for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy.[346] 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.[17] 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.[347] The song "All the Way" won the Academy Award for Best Original Song.[348]

Sinatra in Pal Joey (1957)

In 1958, Sinatra was one of the ten biggest box office draws in the United States.[349] He starred opposite Dean Martin,[350] 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".[351] 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,[352][353] 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.[354] 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, [355][356] filmed on Miami Beach, Florida over the winter of 1958.[357] "High Hopes", sung by Sinatra in the film, won the Academy Award for Best Original Song,[358] and became a chart hit, lasting on the Hot 100 for 17 weeks.[359]

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.[360] 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.[360] For his performance in Come Blow Your Horn he was nominated for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy.[361]

Sinatra as Tony Rome

Though Von Ryan's Express (1965) was a major success,[362][363] and he had also directed None but the Brave in 1965,[364] 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.[365][u] In the late 1960s, Sinatra became known for playing detectives, notably Tony Rome in Tony Rome (1967) and its sequel Lady In Cement (1968).[368][369] He also played a similar role in 1968's The Detective.[370]

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.[371] The film was panned by the critics.[372] 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. Santopietro noted that Sinatra gave an "extraordinarily rich", heavily layered characterization, one which "made for one terrific farewell" to his film career.[373]

Sinatra, the musician[edit]

While Sinatra never formally learned how to read music, he had a fine, natural understanding of it.[374] Early voice coach John 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".[51] Tommy Dorsey observed that Sinatra would "take a musical phrase and play it all the way through seemingly without breathing for eight, ten, maybe sixteen bars." Dorsey was a considerable influence on Sinatra's techniques for his vocal phrasing with his own exceptional breath control on the trombone,[375] and Sinatra regularly swam and held his breath underwater, thinking of song lyrics to increase his breathing power.[79] and

In the mid 1940s after hearing an air check of some compositions by Alec Wilder which were for strings and woodwinds, Sinatra inquired whether there were more works like this by Wilder and set about having them recorded. In 1945, Sinatra was the conductor at Columbia Records for six of Wilder's compositions: "Air for Oboe", "Air for English Horn", "Air for Flute", "Air for Bassoon", "Slow Dance” and "Theme and Variations".[v] The works combine elements of jazz and classical music; composer Wilder considered the Sinatra-led recordings the best renditions of his compositions-past or present.[374]

At a recording session, Sinatra listened as arranger Claus Ogerman ran through a composition. Sinatra told Ogerman he thought he heard "a couple of little strangers" in the string section. Ogerman made corrections to what were thought to be copyist’s errors. Composer Lyn Murray was with Sinatra in Las Vegas as he conducted the orchestra while rehearsing for an engagement there. Sinatra spent 21 hours conducting the orchestra. When Sinatra was though rehearsing and conducting, Murray said, "Every word of each lyric was laid out like a jewel on black velvet."[374]

Critic Gene Lees was also a lyricist and the author of the words to the Jobim melody "This Happy Madness"; he described the song as being quite difficult to sing. After hearing the song as a cut on the album Sinatra & Company, Lees could not describe his amazement that Sinatra caught every aspect of the lyrics he intended when writing them. Lees went on to say that Sinatra captured everything the song said and everything it did not.[376]

Personal life[edit]

Relationships and personality[edit]

Ava Gardner, Sinatra's wife from 1951 to 1957

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,[377] and gossip magazines published details of affairs with the likes of Marilyn Maxwell and Lana Turner.[378][w] Sinatra was married to Hollywood actress Ava Gardner from 1951 to 1957. It was a turbulent marriage, with many well-publicized fights and altercations,[380] and an abortion in November 1952,[381] and the couple formally announced their separation on October 29, 1953 through MGM.[382] 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.[383] Sinatra 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.[x][385] Sinatra took responsibility for Gardner's business affairs long after the split, and was still dealing with her finances in 1976.[386] Sinatra reportedly broke off engagements to Lauren Bacall in 1958,[387] and Juliet Prowse in 1962.[388] Sinatra was later married to Mia Farrow (m. 1966–1968),[389] and finally to Barbara Marx (m. 1976–1998; his death).[390] In a 2013 interview Farrow admitted that Sinatra may be the father of her son, Ronan Farrow (born 1986).[391][389]

Sinatra in 1957

Jo-Caroll Dennison commented that Sinatra had "great inner strength", and that his energy and drive was "enormous". [150] A workaholic, he reportedly only slept for four hours a night on average.[392] Impeccable with his dress[y] and cleanliness, while with the Tommy Dorsey band he developed the nickname "Lady Macbeth", because of frequent showering and switching his outfits.[394] In his spare time, Sinatra enjoyed listening to classical music, and would attend concerts when he could.[395] Throughout his life, Sinatra had mood swings and bouts of mild to severe depression,[396] admitting to an interviewer in the 1950s that "I have an over-acute capacity for sadness as well as elation".[397] 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".[398] Yet Sinatra was known for his generosity, particularly after his comeback.[z] Though Sinatra was critical of the church on numerous occasions,[400] and had an Albert Einstein-like view of God in his earlier life,[401] he turned to the Catholic Church for healing after his mother died in a plane crash late in 1976. He died as a practicing Catholic and had a Catholic burial.[402]

Alleged organized-crime links and Cal Neva Lodge[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".[403] In his 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.[404] Sinatra was present at the Mafia Havana Conference in 1946,[405] and when the press learned of Sinatra being in Havana with Lucky Luciano, one newspaper published the headline, "Shame, Sinatra".[406] 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. [407] She also quotes Jo-Carrol Silvers in saying that he "adored" Bugsy Siegel, and would boast about him to friends and how many people he had killed. [408] Kelley claims that Sinatra and mobster Joseph Fischetti had been good friends from 1938 onward, and acted like "Sicilian brothers".[409] She also states that Sinatra and Hank Sanicola were financial partners with Mickey Cohen in the gossip magazine Hollywood Night Life.[410]

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.[411] 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.[412] 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.[413] Sinatra denied Mafia involvement,[414] declaring that "any report that I fraternised with goons or racketeers is a vicious lie".[414]

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.[415] Sinatra's gambling license was temporarily stripped by the Nevada Gaming Control Board in 1963 after Giancana was spotted on the premises.[416][aa] 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.[418]

Politics and activism[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. His mother, Dolly Sinatra (1896–1977), was a Democratic Party ward leader.[28] Sinatra met President Franklin D. Roosevelt in 1944, an subsequently heavily campaigned for the Democrats in the 1944 presidential election.[419] He made national broadcasts on the radio in support, spoke at Carnegie Hall, and spoke at Madison Square Garden on October 29, 1944, a week before the election.[420] According to Jo Carroll Silvers, in his younger years Sinatra had "ardent liberal" sympathies, and was "so concerned about poor people that he was always quoting Henry Wallace".[421] 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.[422] His comments, while praised by liberal publications, led to accusations by some that he was a Communist, which he strongly denied.[423] In the 1948 presidential election, Sinatra actively campaigned for President Harry S. Truman.[424] In 1952 and 1956, he also campaigned for Adlai Stevenson.[424]

Of all the U.S. Presidents he associated with during his career, he was closest to John F. Kennedy.[424] Sinatra often invited Kennedy to Hollywood and Las Vegas, and two would womanize and enjoy parties together.[425] 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.[424][426] Sinatra's move toward the Republican party seems to have begun when he was snubbed by President Kennedy in favor of Bing Crosby,[427] 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.[ab] 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.[429] Sinatra was fuming and "deeply humiliated" at being rejected, smashing up the concrete of the heliport himself with a sledgehammer.[430] Despite the snub, when he learned of Kennedy's assassination he reportedly sobbed in his bedroom for three days.[424][ac]

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.[432] 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,[424] though it wasn't until July 1972 that officially changed allegiance when he supported Richard Nixon for re-election in the 1972 presidential election. During Nixon's Presidency, Sinatra visited the White House on several occasions.[424] In the 1980 presidential election, Sinatra supported Ronald Reagan and donated $4 million to Reagan's campaign.[433] He sponsored the initial fundraising campaign in the northeast, raising over $250,000 in Boston.[434] 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.[435] 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.[436]

Racial activism[edit]

Sammy Davis, Jr. at a 1963 Civil Rights Convention

From his youth, Sinatra displayed sympathy for African Americans and worked both publicly and privately all his life to help them win equal rights. He blamed racial prejudice on the parents of children.[437] Sinatra felt so strongly about prejudice that Orson Welles recalled one incident where he slugged the bartender of a saloon because he refused to serve his friend, a black musician.[438] He 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 went against policy by inviting Nat King Cole into the dining room,[439] and in 1961, when an African-American couple entered the lobby of the hotel and were blocked by the security guard, Sinatra claimed that they were his guests and let them in. After extensive pressure on the hotel management by Sinatra and Sammy Davis, Jr., the hotel soon began hiring black waiters and busboys.[440] Sinatra's stance, however, didn't stop the occasional racist jibe from him and the other Rat Pack members towards Davis, Jr. at concerts.[203]

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. 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.[441] When he changed his political affiliations in 1970, Sinatra became less outspoken on racial issues.[284]


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.[302] 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.[302]

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.[442][443] 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.[444] He had made no public appearances following a heart attack in February 1997.[442] Sinatra's wife encouraged him to "fight" while attempts were made to stabilize him, and his final words were, "I'm losing."[445] 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."[446] 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.[447][443]

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.[448] Gregory Peck, Tony Bennett, and Sinatra's son, Frank, Jr. addressed the mourners, who included many notable people from film and entertainment.[445][448] 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.[449][450] 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.[451] Significant increases in sales worldwide were reported by Billboard in the month of his death.[224]

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.[452] 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.[453]

In Sinatra's native New Jersey, Hoboken's Frank Sinatra Park, the Hoboken Post Office,[454] and a residence hall at Montclair State University were named in his honor.[455] 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,[456] and the Frank Sinatra Hall at the USC School of Cinematic Arts in Los Angeles, California, dedicated in 2002.[457] Wynn Resorts' Encore Las Vegas resort features a restaurant dedicated to Sinatra which opened in 2008.[458] Items of memorabilia from Sinatra's life and career are displayed at USC's Frank Sinatra Hall and Wynn Resort's Sinatra restaurant.[457][458] Near the Las Vegas Strip is a road named Frank Sinatra Drive in his honor.[459]

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.[460] 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".[461] 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.[462][463]

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.[464][454] 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.[465]

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.[466]

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.[467] A 1998 episode of the BBC documentary series Arena, The Voice of the Century, focused on Sinatra.[468] Alex Gibney directed a four part biographical series on Sinatra, All or Nothing At All, for HBO in 2015.[469]




Frank Sinatra co-wrote the following songs:

See also[edit]



  1. ^ The house at 415 Monroe Street no longer exists and burned down before Sinatra's death,[7] but at 417 is a small building with "From Here to Eternity" and an Oscar on the front sign.[8] It was opened as a museum by Ed Shirak in 2001, but had to be closed after five years due to maintenance issues. At 415 there is now an archway and a bronze plaque with his name and "The Voice".[7]
  2. ^ Dolly was reportedly arrested six or seven times and convicted twice for providing illegal abortions,[27][28] the first of which was in 1937.[29]
  3. ^ 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".[43]
  4. ^ Kelley claims that the jealousy exhibited by the group members often led to brawls in which they would beat up the small, skinny young Sinatra.[57]
  5. ^ Only one copy of this recording was made, a 78 rpm disc. Mane wrote "Frank Sinatra" on the record label and kept the recording in a drawer through the years, giving Sinatra a copy on a cassette tape as a gift in 1979. 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.[65]
  6. ^ "From the Bottom of My Heart" was US Brunswick No. 8443 and UK Columbia #DB2150.
  7. ^ the vocalist, not to be confused with the comedian Jack E. Leonard
  8. ^ 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."[90] 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.[91]
  9. ^ 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".[146]
  10. ^ 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.[156]
  11. ^ 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.[161][162] "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.[163] Initially, Sinatra went along with this approach, but eventually he came to resent Miller for the poor quality of material he was being offered.[164]
  12. ^ Kelley claims that Sinatra bought a two percent share in the hotel for $54,000. At one point the share reached nine percent.[176] He was reportedly ordered to sell his interest in the Sands in 1963, due to his association with mobster Sam Giancana.[177]
  13. ^ Sinatra was not very enthusiastic about the song initially. His friend, Jimmy Van Heusen, convinced him that the song would be a success.[188]
  14. ^ 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.[192]
  15. ^ 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."[212]
  16. ^ 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.[236]
  17. ^ Normal limits for the game are US$2,000 per hand; Sinatra had been playing for US$8,000 and wanted the stakes to be raised to US$16,000. Sinatra also wanted to be able to play for the higher stakes on credit.[252]
  18. ^ Horne developed vocal problems and Sinatra, committed to other engagements, could not wait to record.
  19. ^ Sinatra successfully later sued a BBC interviewer who claimed that he'd used his Mafia connections to get the part.[327]
  20. ^ 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.[334]
  21. ^ The film was later made by Stanley Kubrick in 1971 and is now considered to be one of the greatest films of all time.[366][367]
  22. ^ Mitch Miller played English horn and oboe on the Sinatra-led recordings.[374]
  23. ^ Turner later denied the claims in her 1992 autobiography, saying that "the closest things to dates Frank and I enjoyed were a few box lunches at MGM".[379]
  24. ^ 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.[384]
  25. ^ 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.[393]
  26. ^ Kelley notes that 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.[399] In another instance, after a heated argument with manager Bobby Burns, rather than apologize, Sinatra bought him a brand new Cadillac.[67]
  27. ^ 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. The two men never spoke again.[417]
  28. ^ 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".[428]
  29. ^ When Sinatra 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.[431]


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