His family moved from the island of Jamaica to Brooklyn, New York City when Kelly was four, and he started his professional career as a teenager, initially as a member of R&B groups. After working in the big band and small groups led by Dizzy Gillespie, he was a member of Miles Davis' Quintet from 1959 to 1963.
Wynton Kelly was one of the most prolific sideman pianists of his era, performing on scores of jazz albums, and led albums under his own name for the Riverside and Vee-Jay labels. After leaving Davis's group, along with Paul Chambers and Jimmy Cobb, he formed a trio which worked regularly during the 1960s.
A superb accompanist loved by Miles Davis and Cannonball Adderley, Wynton Kelly was also a distinctive soloist who decades later would be a strong influence on Benny Green. He grew up in Brooklyn and early on played in R&B bands led by Eddie “Cleanhead” Vinson, Hal Singer, and Eddie “Lockjaw” Davis. Kelly, who recorded 14 titles for Blue Note in a trio (1951), worked with Dinah Washington, Dizzy Gillespie, and Lester Young during 1951-1952.
After serving in the military, he made a strong impression with Washington (1955-1957), Charles Mingus (1956- 1957), and the Dizzy Gillespie big band (1957), but he would be most famous for his stint with Miles Davis (1959-1963), recording such albums with Miles as Kind of Blue, At the Blackhawk, and Someday My Prince Will Come. When he left Davis, Kelly took the rest of the rhythm section (bassist Paul Chambers and drummer Jimmy Cobb) with him to form his trio