Charles's film debut was in fellow Baltimore native John Waters' Hairspray in 1988. The following year, he starred alongside Robin Williams and Ethan Hawke in the Oscar-winning Dead Poets Society. Subsequent film roles have included Don't Tell Mom the Babysitter's Dead, Threesome, Pie in the Sky, Muppets from Space, S.W.A.T, Four Brothers, After.Life, Crossing the Bridge, and Brief Interviews with Hideous Men.