He started playing the drums at four and was performing locally in his own band by the age of eight, and playing music with other kids in the neighborhood, including childhood friends Victor Wooten and the other Wooten brothers,[1] who lived a few doors away and through whom he met Consuela Lee Moorehead, composer, arranger, music theory professor, and the founder of the Springtree/Snow Hill Institute for the Performing Arts.

He attended Shenandoah College and Conservatory of Music on a Classical Percussion scholarship and, upon leaving school, became a member of a local Top 40 band called The Squares with bassist Oteil Burbridge.

During this period he also formed long-term musical associations with Joe Henderson, Bobby Hutcherson, Buster Williams, James Moody, JJ Johnson, Andrew Hill, and others.

[3] His most recent album, Valse Sinistre, leading his band Freedom of Ideas, with Micah Thomas, Dezron Douglas and Dayna Stephens, came out on the Canadian Cellar Live label in August 2022.

A sideman on over 350 records, Drummond has played and recorded with, among others, Bobby Hutcherson, Nat Adderley, Ralph Moore, Buster Williams, Charles Tolliver, Lew Tabackin and Toshiko Akiyoshi, Hank Jones, James Moody, Sonny Rollins, Andy LaVerne, Lee Konitz, Dave Stryker, George Colligan, Ted Rosenthal, Bruce Barth, Joe Lovano, Andrew Hill, Larry Willis, Toots Thielmans, Freddie Hubbard, Chris Potter, Eddie Gómez, Stanley Cowell, Javon Jackson, and Sheila Jordan.