Hustle and Flow (2005) Directed by Craig Brewer

From Wikipedia: Hustle & Flow is a 2005 independent film written and directed by Craig Brewer about a Memphis hustler called DJay, played by Terrence Howard, who experiences a midlife crisis and is compelled to face his aspiration to become a rapper.

The film, like its own plot, has had a hard life. It experienced many years of near-misses and outright rejection from major studios and potential financiers before finally being backed by its longtime supporter John Singleton (who says in the DVD extras that he decided at last to put up the money himself because he was exasperated at his friends not getting what their film deserved). Once it got made, it was nominated for two Academy Awards: for Best Actor for Howard, and won an Academy Award for Best Original Song, for Three 6 Mafia’s “It’s Hard out Here for a Pimp”.