Drummond learned jazz at an early age from his father (a drummer and a jazz enthusiast) and started playing in pop soul bands at the age of eight. He studied at Shenandoah Conservatory, and performed around Newport News, before moving to New York at the behest of Al Foster in 1986. Since then Drummond has performed and/or recorded with some of the greatest jazz musicians in the world, including oe Henderson (1988-89), Horace Silver(1989), Bobby Hutcherson (1990 to the present), Buster Williams (1990-93), Charles Tolliver (1991), Hank Jones (1991), Nat Adderley (1991), John Swana (1991, 1993), Vincent Herring (1991-93), James Moody (early 1990s), Steve Kuhn (from 1992 to the present), Sonny Rollins (1994-95), Chris Potter (1998), Ralph Moore (from 1989), John Faddis (1989-91), Walt Weiskopf (1990 to 2002), Andy LaVerne (1994), Lee Konitz (1995 -2006), Dave Stryker (1996), George Colligan (1997), Ted Rosenthal, Geri Allen, Bruce Barth, Jonny King, David Hazeltine, Joe Locke, Sheila Jordan (1995 to the present), Andrew Hill (1997-2000), Archie Shepp (1999-2002), Larry Willis (2006 to the present), Eddie Henderson (1996 to the present), Javon Jackson (1997 to the present) and Freddie Hubbard (mid-1990s). He is currently a member of Carla Bley and the Lost Chords (2001 to the present), the Larry Willis Band, the Steve Kuhn Trio and his own New York-based trio, Freedom of Ideas, which represents an amalgamation of all of the musical experiences he has had over his long career. He is currently also Professor of Jazz Drums at the Juilliard School of Music and NYU in New York.
As a much in demand sideman, Drummond has played on over 200 recordings. He has recorded six CDs as a co-leader (with The Drummonds, Native Colours and the album Mysterious Shorter with Nicholas Payton, Bob Belden, John Hart and Sam Yahel), and three CDs as a leader: Native Colours, The Gift and Dubai (Criss Cross Jazz). Jazz Times magazine said of The Gift, "the recording has a richness and total lack of clichés ... imaginative, satisfying and memorable" and of Dubai, his third solo release, "Drummond's nimble, pianoless quartet spins jazz on the head of a pin with stunning results."