Sweet and Lowdown

Released 1999
Stars Sean Penn, Samantha Morton, Uma Thurman, Brian Markinson, Anthony LaPaglia, Gretchen Mol
Directed by Woody Allen

Emmet Ray is like a man with a very large dog on a leash. The dog is his talent, and it drags him where it wants to go. There are times in "Sweet and Lowdown" when Ray, "the second-best jazz guitarist in the world," seems almost like a bystander as his fingers and his instinct create heavenly jazz. When the music stops, he's helpless: He doesn't have a clue when it comes to personal relationships, he has little idea how the world works, and the only way he can recognize true love is by losing it.

Emmet Ray is a fictional character, but so convincing in Woody Allen's "Sweet and Lowdown" that he seems like a real chapter of jazz history we somehow overlooked. Sean Penn, whose performances are master classes in the art of character development, makes him into an exasperating misfit whose sins are all forgiven once he begins to play. With his goofy little mustache and a wardrobe that seems patterned on second-hand guesses about what a gypsy jazzman in Paris might wear, Emmet Ray looks like a square peg lacking even the round hole.

Here is a man, who, when we first meet him, is already considered peerless among American jazz guitarists, yet is running a string of hookers as a sideline. Who drinks so much that only sheer good luck spares him, night after night, from getting himself killed. Who is forgiven by his colleagues, most of the time, because when he plays, there is magic happening right there on the stage.

Summary by Roger Ebert