Director's first film role was in 1998's He Got Game, directed by Spike Lee. This was followed by Summer of Sam in 1999 and Bamboozled in 2000, both films also directed by Lee. Her breakout performance came in the film Book of Shadows: Blair Witch 2 as the hard-core Goth girl, Kim Diamond. She went on to act in the independent films Unforeseen, Tony n' Tina's Wedding, Charlie's Party, Live Free or Die, Life is Short and A Crime with Harvey Keitel. Director reunited with Spike Lee for the film She Hate Me in 2004, and in 2006 played Stevie the bank robber in Lee's Inside Man.