In the 1930s, Emmet Ray (SEAN PENN) is a gifted, but troubled jazz guitarist who's considered to be the best in the world, second only to the legendary Django Reihhardt. While the thought or site of that man sends Emmet into a paranoid tizzy, he otherwise spends his time boozing it up, pimping for some young women and generally living life by his own terms.
As such, he loves women but hates the thought of settling down. Thus, once free of his latest "girlfriend," Emmet heads out with his buddy Bill Shields (BRIAN MARKINSON) where they meet a young mute woman, Hattie (SAMANTHA MORTON), and her friend. While Emmet isn't happy to have a woman who can't speak, they sleep together and soon become something of a romantic item.
Yet, Emmet's lackadaisical demeanor and boozing ways puts both his paying gigs and relationship with Hattie in jeopardy. Over time, he eventually meets another woman, Blanche (UMA THURMAN), a writer with a desire to know what goes through the minds of people in various professions. Although they quickly get married, she eventually has a fling with Al Torrio (ANTHONY LaPAGLIA), a bodyguard with a dangerous reputation that titillates her.
As Emmet continues in the shadows of Django's reputation, he begins to realize that his life isn't as ideal as he would like, and that he may have thrown away his best chances at happiness.