Kelly grew up in Brooklyn after his family moved from Jamaica, and he was playing professionally while still a teenager — gigging with rhythm and blues bands before he'd fully formed his jazz vocabulary. That early R&B work stuck. Even at his most sophisticated harmonically, there's a looseness and a groove in his playing that most bebop pianists never quite managed. He swings without making a production of it.

The Miles Davis association is the first thing most people encounter, and it's not a bad entry point. Kelly appears on Kind of Blue (1959), but only on one track — "Freddie Freeloader" — while Bill Evans handles the rest of the album. That says something about what Davis was after: Kelly for the blues-drenched, straight-ahead feeling; Evans for the impressionistic, harmonically open stuff. Kelly never seemed bothered by the comparison, and he shouldn't have been. His contribution to that record hits differently than Evans's does, and both are essential.

After leaving the Miles Davis group in 1963, Kelly took Paul Chambers and Jimmy Cobb with him and formed the Wynton Kelly Trio. This is where he really stretches out. Albums like Wynton Kelly! (1961) and Full View (1967) show a pianist who was confident enough to let a lot of air into his playing — he doesn't fill every bar, and the rhythm section breathes with him. The trio had a chemistry that comes through clearly on record, and they were reportedly an extraordinary live band.

He also spent several years as Wes Montgomery's working trio on the road and on records. Smokin' at the Half Note (1965) is the document of that partnership, and if you haven't heard it, stop reading and go find it. Montgomery's guitar and Kelly's piano fit together in a way that sounds completely natural — neither one is accommodating the other, they're just playing the same language. It's the kind of record that makes you wonder why musicians ever play with anyone else once they find this kind of connection.

Kelly died in 1971 at 39 from an epileptic seizure, which is one of jazz's genuinely painful what-ifs. He was still developing, still working, and the trio was as tight as ever. What he left behind is substantial — dozens of sideman appearances, a handful of excellent trio records, and a reputation among pianists as someone who understood swing at a cellular level. He never chased trends, never tried to sound modern for its own sake. He just played, and it was almost always exactly right.