Sweet and Lowdown
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Sweet and Lowdown is a 1999 film which tells the story of an arrogant, obnoxious, alcoholic jazz guitarist named Emmet Ray who may just be the best guitarist in the world. (Or second, if you count his idol, Django Reinhardt.) Although the story is told as a documentary, the main character, Emmet Ray, is fictional. It stars Sean Penn, Samantha Morton, Uma Thurman and Woody Allen.
The movie was written and directed by Woody Allen. The movie is a fine example of Allen's directorial style and is revered as one of his best works.
It was nominated for Academy Awards for Best Actor in a Leading Role (Sean Penn) and Best Actress in a Supporting Role (Samantha Morton).