In 1993 a young Michael Rapaport made his film debut in Zebrahead, receiving great critical acclaim for his genuine and confident portrayal of a Jewish teenager growing up in a predominantly African-American Detroit neighborhood. The performance went on to garner him an Independent Spirit Award nomination and the film itself won the 1993 Sundance Film Festival’s Filmmaker’s Trophy.

In 2003, Rapaport wrapped production on the dramatic thriller 29 Palms. Executive-produced by Rapaport, the film co-stars Chris O’Donnell and Rachel Leigh Cook. In 2002 Rapaport starred in the independent dark comedy Comic Book Villains opposite Natasha Lyonne and Cary Elwes. He also starred opposite Woody Allen and Hugh Grant in the comic caper Small Time Crooks, gave a controversial performance alongside Damon Wayans and Jada Pinkett-Smith in Bamboozled, starred in the period drama Men of Honor with Robert DeNiro and Cuba Gooding Jr., co-starred with John Travolta in Lucky Numbers and appeared in the sci-fi thriller The Sixth Day with Arnold Schwarzenegger.

His additional film credits include Higher Learning, Kiss of Death, Mighty Aphrodite, Beautiful Girls, Metro, A Brother’s Kiss, Cop Land, Kicked in the Head, True Romance, The Pallbearer, Illtown, Palmetto and Deep Blue Sea. No stranger to television, Rapaport also appeared as a recurring guest on Friends as Phoebe’s (Lisa Kudrow) boyfriend.

Rapaport formed his own production company, Release Entertainment, which produced a series of ten short films for the Internet — 10 Items or Less — for Atom Films.