Hoffman's first role was as a defendant in a 1991 episode of the television series Law & Order. He made his film breakthrough in 1992 when he appeared in four feature films, with the most successful film being Scent of a Woman, in which he played a backstabbing classmate of Chris O'Donnell's character. He had been stocking shelves at a city grocery at the time before landing the role and credits the film to kickstarting his career.

Hoffman has established a successful and respected film career playing diverse and idiosyncratic characters in supporting roles, working with a wide variety of noted directors, including Paul Thomas Anderson, The Coen Brothers, Cameron Crowe, Spike Lee, David Mamet, Robert Benton, Todd Solondz and Anthony Minghella; notably, he has appeared in four out of five of Anderson's feature films to date (Hard Eight, Boogie Nights, Magnolia, and Punch-Drunk Love).

He appeared in Last Party 2000, a documentary about the 2000 U.S. elections. Througho