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Starting out at the age of 15, McKenna played with Boots Mussulli (1947), Charlie Ventura (1949) and Woody Herman's Orchestra (1950–51). He then spent two years in the military, and re-joined Ventura (1953–54).
He worked with a variety of top swing and Dixieland musicians including Gene Krupa, Joe Venuti, Stan Getz, Zoot Sims, Al Cohn, Bob Wilbur, Eddie Condon, and Bobby Hackett but became primarily a soloist after 1967, especially in the Northeast United States. McKenna performed with Louis Armstrong at the 1970 Newport Jazz Festival.
He started to be recognized in his own right during the 1970s, but chose to play in his local area rather than travel extensively. He preferred playing in clubs and hotels over getting center stage in major venues. He could be found playing in hotel piano bars in Massachusetts, including a decade-long run at Boston's Grand Dame Copley Plaza Hotel, that ended in 1991, when the Plaza was sold. The new owners briefly turned the Plaza Bar into a cabaret, but the new format was never as popular as Mckenna and ended within a year. Unfortunately, the damage was done and, because McKenna was much in demand, he only returned to the Plaza for a single night.
Because of his fondness for staying close to the melody, McKenna often said, “I’m not really a bona fide jazz guy”. Instead, he claimed, “I’m just a saloon piano player.” Regulars at the Copley Plaza Bar (now the Oak Room) rebuffed this modest remark by telling McKenna that he was “just a saloon player” like Billie Holiday was “just a saloon singer”. McKenna was a loyal Boston Red Sox fan who, to the amusement of fans and fellow musicians alike, would often listen to games on his transistor radio while performing. Since Mckenna did not drive, he often told friends that the best thing about staying at the Plaza six nights a week was being able to walk to his beloved Fenway Park. In a fitting tribute, Red Sox radio announcer Joe Castiglione took time on-air during a game to say a few words about the passing of one of Boston's great, largely unsung talents. McKenna retired around the turn of the millennium due to increasing mobility problems brought on by his long battle with diabetes.
McKenna was also known as a wonderful accompanist, recording with such singers as Rosemary Clooney, Teddi King and Donna Byrne and recording a PBS special with Tony Bennett.
Dave McKenna died in 2008 from lung cancer. Survivors included his wife, Frances (Wiggins) McKenna (now deceased), of Oak Island, N.C.; two sons, Douglas of Cape Cod; Stephen and his wife Hiya and daughter, Caitlin, all of PA. He also leaves a brother, Donald; two sisters, Jean O’Donnell and Patricia Savard, all of R.I.
Musical style 
His musical presentation relies on two key elements relating to his choices of tunes and set selection, and the method of playing that has come to be known as "three-handed swing".
McKenna liked to make thematic medleys, usually based around a key word that appears in the titles, such as teach, love, women's names, dreams, night or day, street names, etc. There may be ballads and up-tempo songs blended together with standards, pop tunes, blues, and even TV themes or folk material.
McKenna's renditions usually began with a spare, open statement of the melody, or, on ballads, a freely played, richly harmonized one. He often stated the theme a second time, gradually bringing more harmony or a stronger pulse into play.
The improvisation then began in earnest on three levels simultaneously, namely a walking bass line, midrange chords and an improvised melody. The bass line, for which McKenna frequently employs the rarely-used lowest regions of the piano, is naturally being played in the left hand, often non-legato, to simulate an actual double bassist's phrasing, the melody in the right. The chords are interspersed using the thumb and forefinger of the right hand or of both hands combined, if the bass is not too low to make the stretch unfeasible. Sometimes he also adds a guide-tone line consisting of thirds and sevenths on top of the bass, played by the thumb of the left hand.
His famous four-to-the-bar "strum" is achieved by the left hand alone, playing a bass note (root/fifth/other interval) plus third and seventh, leading to frequent left-hand stretches of a tenth, which is why these voicings frequently appear arpeggiated, with the top two notes being played on the beat, the bass note slightly before. These voicings are often subtly altered every two beats, for variety. This playing style is frequently mistaken for a stride piano, which it is clearly not, as it is of a four-beat nature, as opposed to the two-beat "oom-pah" of true stride piano, as exemplified by Fats Waller, James P. Johnson, and the like. McKenna usually reserves all-out stride for sections where a bassist would play half notes, i.e. ballads and Dixieland-tinged material. The result is the sound of a three piece band under one person's creative control.
McKenna can weave a spontaneous melodic line, usually with lots of chromaticism and blues licks, over the bass line. The bass can be anything from single notes to repeated chords like a rhythm guitar to a full-blown stride piano, the latter often reserved for the height of a song's development.
The characteristic that perhaps most distinguishes McKenna's playing is his sense of time. One of the most commonly cited difficulties of solo jazz piano is the need to provide a compelling time feel, in part by emulating the rhythmic landscape normally provided by three or four players in a small group. By conceiving of multiple "parts" and playing them with distinct volume levels and time feels (often with right hand chords ahead of the beat and the melody behind the beat), McKenna showed a unique ability to reproduce the small group sound on the piano.
His recordings on the Concord record label attest to both the excitement and tenderness of his playing. His contribution to the development of jazz piano as a solo voice will not be forgotten by musicians or the history books. Art Tatum, often considered the greatest soloist in jazz piano history, praised McKenna as someone he considered a complete musician.
McKenna has had an extensive recording career from 1958 to 2002, and recorded for ABC-Paramount Records (1956), Epic (1958), Bethlehem (1960) and Realm (1963). McKenna made several recordings for Chiaroscuro Records in the 1970s, including his comeback album "Solo Piano". McKenna debuted with Concord in 1979, where the majority of his catalogue rests, including one volume of Concord's 42-disc series recorded live inside Maybeck Recital Hall. McKenna's last recording, "An Intimate Evening With Dave McKenna" was released on Arbors Records in 2002.
Selected discography 
- Giant Strides, 1979, Concord Records
- Bill Evans: A Tribute, 1982, Palo Alto Records
- A Celebration of Hoagy Carmichael, 1983 Concord Records
- Dancing in the Dark and Other Music of Arthur Schwartz, 1986 Concord Jazz
- My Friend the Piano, 1987 Concord Jazz
- No More Ouzo for Puzo, 1989 Concord Jazz
- Christmas Ivory, 1997 Concord Jazz
- An Intimate Evening With Dave McKenna, 2002 Arbors Records
- Keepnews, Peter (October 20, 2008). "Dave McKenna, Pianist Known for Solo Jazz Work, Dies at 78". NY Times. Retrieved 2008-10-20.
- All Music
- New England Jazz History Database – Dave McKenna Search