Born in Newport News, Virginia, Drummond grew up listening to his father's extensive jazz record collection (including Max Roach, Miles Davis, James Moody, Horace Silver, Freddie Hubbard, Sonny Rollins and The Three Sounds). Encouraged by his father, also a drummer and saxophonist, he was given his first drum at the age of four and was playing in local bands (including the elementary school band, where he learned to read music) by the time he was eight. After graduating from Shenandoah Conservatory of Music, where he studied classical percussion for two years before switching to jazz, Drummond moved to New York, at the behest of Al Foster in 1988, and was almost immediately recruited to the young band Out of the Blue (OTB), recording Spiral Staircase for Blue Note Records, before becoming a member of Horace Silver's Sextet.
Since then, Drummond's highly musical, versatile and powerful playing has been called upon in the studio and on the bandstand by the jazz world's elite, including Joe Henderson, Bobby Hutcherson, Carla Bley (as a member of Carla Bley and the Lost Chords), Chris Potter, Lee Konitz, Eddie Gomez, Buster Williams, Nat Adderley, George Cables, Charles Tolliver, Andrew Hill, Steve Kuhn, Hank Jones, Joe Lovano, Christian McBride, Joe Locke, NEA Sheila Jordan, Larry Willis, Javon Jackson, Archie Shepp, Charles McPherson, Tony Malaby, Eric Reed, Eddie Henderson, Marty Ehrlich and international artists Franco Ambrosetti (Switzerland), Karin Krog (Norway), Sadao Wantanabe (Japan), Toots Thielmans (Belgium), Barney Wilen (France), Tommy Smith (Scotland), Yakov Okun (Russia) and Tony Lakatos (Hungary).
Drummond, while continuing to maintain a busy touring schedule, is also a highly respected educator. He is currently Professor of Jazz Drums at the Juilliard School of Music and NYU in New York and gives private lessons and workshops around the world.