|Genres||Punk rock, hardcore punk, indie rock, folk punk, emo|
|Labels||Vermiform Records, Lookout! Records, Kill Rock Stars|
|Associated acts||Universal Order of Armageddon, Born Against, (Young) Pioneers, Men's Recovery Project, The Great Unraveling, Skull Kontrol, Wrangler Brutes, Oldest|
Headley played drums in the Baltimore-area hardcore/emo band Universal Order of Armageddon from 1992–1994. With Universal Order of Armageddon band mate Tonie Joy, he also joined the final lineup of the political hardcore band Born Against in 1993.
Later that year, he moved to Richmond, Virginia, and co-founded the group (Young) Pioneers, with whom he remained for several years. Through the remainder of the 1990s, he had brief stints in Men's Recovery Project and The Great Unraveling, followed by more extended time in Skull Kontrol and Wrangler Brutes.
In May 2013, Headley won the prestigious "Outstanding Pastry Chef" from the James Beard Foundation for his work at the New York restaurant, Del Posto.