The Thinking Drummer's Pocket
Stewart grew up in Des Moines, Iowa, which is not exactly where you'd expect one of jazz's most distinctive drummers to come from. But he absorbed the tradition seriously — Tony Williams, Elvin Jones, Jack DeJohnette — and then figured out his own way through it. By the time he arrived in New York, he had a voice that was already pretty fully formed, which is unusual for someone that young. He wasn't reinventing anything; he was just doing it better than most people around him.
His association with John Scofield is probably what brought him to the attention of a lot of listeners. The two have a genuinely symbiotic thing going — Scofield's bluesy, off-center guitar lines seem to breathe differently when Stewart is behind the kit. Stewart knows when to push, when to sit back, and when to drop something completely unexpected into the middle of a phrase without wrecking the groove. That's not a small thing. Plenty of technically gifted drummers can't do it.
He also built a deep working relationship with Joe Lovano and Brad Mehldau, among others, and his discography as a sideman is genuinely impressive in its range. He shows up on records across a wide span of the post-bop world and somehow sounds right in all of them. That adaptability isn't blandness — he's recognizably himself on every session. He just happens to be the kind of player who makes other musicians sound better, and they know it.
As a leader, Stewart has made records that deserve more attention than they typically get. Snide Remarks (1996) and Telepathy (1997) are good places to start — they're not flashy records, but they're smart ones, full of the same conversational quality that defines his sideman work. He writes his own tunes, and they tend to have the same slightly sideways logic his drumming does. Nothing about them announces itself too loudly, which might be why they slip under the radar of people hunting for big statements.
If you're coming to Stewart fresh, the easiest recommendation is just to put on almost anything John Scofield recorded in the 1990s and listen specifically to the drums. You'll hear someone who seems to be thinking about music in complete sentences rather than just keeping time. He's not trying to overwhelm you. He's trying to make the music work, and he does it consistently well enough that it's genuinely surprising more people don't talk about him in the same breath as the drummers who get all the press.