DeWolf is best known for his early career as a slam poetry champion, his award-winning films for Youth Speaks Bigger Picture Project, live tours with the performance trio The Suicide Kings, hosting the monthly Tourettes Without Regrets at the Oakland Metro OperaHouse, and for his work as a producer and performer on NPR's "Snap Judgment". DeWolf has appeared on HBO's "Def Poetry", "60 Minutes", UPN, "Inside Edition", and CBS. DeWolf directed, wrote and starred in the feature film "Smoked. The Movie" (2012).