Sweet and Lowdown(1999)
Woody Allen immerses himself in the world of vintage jazz in this period mock-biography of a musician gifted in his art but a sad student in life. Emmet Ray (Sean Penn) is a 1930s jazz guitarist considered one of the finest musicians ever to touch a fretboard, second only to the legendary Django Reinhardt. For all the passion and sensitivity of his music, Emmet is a louse off-stage; he earned his living as a pimp before gaining fame, and he throws his money away on flashy clothes and big cars, going through women like guitar picks. He also has another charming hobby: shooting rats at the city dump. But when Emmet meets Hattie (Samantha Morton), a shy, mute woman who earns her living doing laundry, he discovers that she loves his music, and he promptly falls for her. However, his inability to be faithful, his arrogant conviction that a musician should never marry, and his belief that he can do better than Hattie eventually doom their relationship. Emmet later marries Blanche (Uma Thurman), a beautiful and refined woman with a career as an author, but she is no more interested in fidelity than he is, and in time he realizes how foolish he was to give up Hattie. Jazz guitarist Howard Alden plays Emmet's solos on the soundtrack, while several authorities on jazz discuss "Emmet's" music, including Nat Hentoff, Douglas McGrath, and one Woody Allen.