Since his first slam in 1999, DeWolf won his way onto seven slam teams, competing on the finals stage at the National Poetry Slam on his first team. He has since become a National Poetry Slam Champion, the Berkeley Grand Slam Champion, a YouthSpeaks Mentor, a featured performer on HBO's "Def Poetry Jam" hosted by Mos Def, appearing in Season Three with his poem "Grim Fairy Tale", and taping for Season Five with Dave Chappelle and Lauryn Hill. DeWolf's style has been described as "raw and raucous." "He brings that same inimitable, avant-garde style to everything he does—poetry, playwriting, performance and his latest endeavor, filmmaking."