The last bunch of albums by John Scofield, Bill's most regular employer, can be heard as a vivid example group interplay as the guitarist, bassist Dennis Irwin and (depending on the recording) saxophonists Joe Lovano or Eddie Harris, and keyboardist Larry Goldings are held together by Bill's distinctive glue much in the tradition of a swinging Jack DeJohnette, a lightning-quick Roy Haynes, an idiosyncratic Ed Blackwell, inspirations all. Bill's respect goes out to a number of other drummers, including Philly Joe Jones, Elvin Jones, and early Tony Williams. No doubt, they've shared what might be heard as Bill's enlarged notion of what their craft is: namely, that they are musicians first, drummers and percussionists second.
After graduating he enrolled at the University Of Northern Iowa in Cedar Falls, playing in the Jazz and marching bands as well as the orchestra. He then transferred to college in Wayne, New Jersey, where he studied with Dave Samuels, Rufus Reid and Harold Mabern. It was here that he met future collaborator, saxophonist Joe Lovano. While still in college he made his recording debut with saxophonist Scott Kreitzer and recorded two further collections with pianist Armen Donelian. After graduation in 1988 he moved to Brooklyn, New York, where he set up home.

There he began the slow process of establishing his reputation by regular appearances at jam sessions and by word of mouth, leading to his first gigs with the Larry Goldings Trio. At one of their regular sessions at Augie's Club in Manhattan, Maceo Parker attended and invited him to contribute to a forthcoming recording date (for Roots Revisited ). Afterwards he was invited to join John Scofield's band, which also included Lovano, who was featured on both of Stewart's early solo albums. The first, Think Before You Think, was issued on the Japanese label Jazz City and featured Dave Holland on bass and Marc Copland on piano in addition to Lovano. The second, Snide Remarks, featured pianist Bill Carrothers, trumpeter Eddie Henderson and bassist Larry Grenadier. This boasted nine original Stewart compositions, highlighting a sophisticated compositional technique that Lovano once analogized as being that of 'a melody player within the concept of rhythm'.

The list of Jazz Artists Bill has performed with includes John Scofield, Pat Metheny, James Brown, Larry Goldings, Peter Bernstein, Joe Lovano, Scott Kreitzer, Maceo Parker, Tim Hagans, Andy LaVerne, Steve LaSpina, Lee Konitz, Marc Copland, Don Grolnick, Fred Wesley, Ron McClure, Seamus Blake, Kevin Hays, Armen Donelian, Larry Grenadier, Bill Carrothers, Steve Wilson, and many more.