[3] In 1994, while in high school, Rolle began an involvement with Art Start as a student in the Media Works Project.
He graduated in 1996 from the New York City Public Repertory Company (an alternative arts high school), where he won the Playwrights Competition.
[2] In 1997, he taught the Media Works Project curriculum to teenagers coming out of Rikers Island prison, and in 1998 he led Art Start's anti-racism public service announcement (PSA) project, which received coverage from the Bravo cable network in the documentary Fire, Risk and Rhythm.
[2] Rolle founded the Hip Hop Project in 1999, with Art Start's support,[1] and which led to collaboration with Russell Simmons and won him praise from people like Doug E.
[3] He was director, actor, and writer for Tomorrow's Future theatre company; his work there included the play A Brooklyn Story.