Drumming began his career writing for the Washington City Paper, and later wrote for Entertainment Weekly and Salon.
He was part of a group of hires by editor David Carr[2] that included several young black writers who went on to become voices of their generation: hired alongside Drumming that year were eventual New Yorker magazine staffer and history professor Jelani Cobb, MacArthur Genius Ta-Nehisi Coates, and performance artist and playwright Holly Bass.
[3] From 2002 to 2007,[4] Drumming worked as an editor and music critic for Entertainment Weekly,[5] later moving to Salon.
Set on November 4, 2008, the night of Barack Obama's historic election as the first black President of the United States,[8] Big Words revolves around three friends who 15 years earlier had had "a promising hip-hop group and are now dealing with the challenges of being in their late 30s.
In a 2015 segment of This American Life, the two discussed the trajectory of their friendship over the next two decades of their personal lives and respective careers in media.