Boogie Nights
This Paul Thomas Anderson film was a 1997 gem that threw Cheadle into the spotlight, albeit briefly, as a comic actor. He didn't have much screen time, but what he had, he showed off every bit of his timing.
The film, set in the backdrop of America's seedy pornographic industry, is a story of a young, well-equipped lad (Mark Wahlberg) achieving dubious stardom with the help of low-rent Hefnerian father figure Jack Horner (Burt Reynolds). The film is about the hope that porn can be art, and the little-known realities the industry faces.
Cheadle plays Buck Swope, a second-tier actor, basically called in as the sidekick when the leading 'performer' is inadequately unable to work the scene, and his goal in life is to be a hi-fi salesman.
He provides the film's brightest, lightest moments, and is one of the most memorable facets of a very good movie.