His film roles include Zebrahead (1992), True Romance (1993), Higher Learning (1995), Metro (1997), Cop Land (1997), Deep Blue Sea (1999), The 6th Day (2000), Dr. Dolittle 2 (2001), Big Fan (2009), and The Heat (2013).

Rapaport's stepfather, comic Mark Lonow, who owned The Improv with Budd Friedman, helped him get into the stand-up world.

[citation needed] In October 2008, Rapaport announced that he was directing a documentary about hip hop act A Tribe Called Quest.

[12] The film, Beats, Rhymes & Life: The Travels of A Tribe Called Quest, was released in 2011 and received mostly positive reviews.

[citation needed] On February 12, 2010, Rapaport participated in the NBA All-Star Weekend's Celebrity Game and was named the MVP because of his defense on football player Terrell Owens, the MVP of the last two Celebrity Games, despite scoring just four points and having only a single rebound.

The film was about the 1970s championship-winning New York Knicks led by Earl Monroe, Walt Frazier, and Willis Reed.

After the October 7, 2023 Hamas-led attack on Israel, Rappaport appeared in many independent activist shorts supporting the release of hostages taken by Hamas and its affiliates.

[25][10] In 2005, Rapaport wrote an article for Jane magazine about having to evict the actress Natasha Lyonne from a property he was renting to her during a period of heavy drug use on her part.

[27] In June 2018, Rapaport, while on an American Airlines flight from Houston to Los Angeles, stopped another passenger attempting to open an emergency door mid-flight.