In 2006, Josh Tyrangiel, music critic for Time, wrote: "What makes Chestnut the best jazz pianist of his generation is a willingness to abandon notes and play space.

[2] Chestnut began learning the piano at the age of seven, and in his boyhood played at Mount Calvary Baptist Church.

[2] In 1985, Chestnut earned a degree in jazz composition and arranging from Boston's Berklee College of Music.

[4] In the late 1980s and early 1990s, Chestnut worked with Wynton Marsalis, Terence Blanchard, Donald Harrison, and other bandleaders.

[6] With Gerald Albright With Carl Allen With Carl Allen & Rodney Whitaker With Tiffany Austin With Gary Bartz With Kathleen Battle With Alexander Berenson With Dee Dee Bridgewater With Jeri Brown With Ronnie Burrage With Ann Hampton Callaway With Betty Carter With James Carter With Michael Carvin With Freddy Cole With Carla Cook With Elvis Costello and the Brodsky Quartet With Dee Daniels With Michael Dease With Dr. John and the Donald Harrison Band With Cynthia Felton With The Dizzy Gillespie All-Star Big Band With Jimmy Greene With Mark Gross With Roy Hargrove With Donald Harrison With Vincent Herring With Laird Jackson With Denise Jannah With George Kawaguchi With The Keystone Quartet With Kevin Mahogany With Wynton Marsalis With Christian McBride With Bette Midler With Charnett Moffett With George Mraz With Roy Nathanson With Chiara Pancaldi With Madeleine Peyroux With Morris Robinson With Jackie Ryan With Ameen Saleem With Andy Scott With Jimmy Scott With Marilyn Scott With Bud Shank With Jae Sinnett With Billy Taylor With Joris Teepe and The Don Braden Quintet With Tim Warfield With Sadao Watanabe With Kim Waters With Rodney Whitaker With Phil Wilson's Rainbow Band With Steve Wilson With Joh Yamada With Dave Young