Emmet Ray (Sean Penn) is jazz guitarist who achieved some acclaim in the 1930s with a handful of recordings for RCA Victor, but who faded from public view under mysterious circumstances. Though a talented musician, Ray's personal life is a shambles. He is a spendthrift, womanizer and pimp who believes that falling in love will ruin his musical career. Due to his heavy drinking, he's often late or even absent for performances with his quintet. After music, his favorite hobby is shooting rats at garbage dumps. Ray idolizes famed guitarist Django Reinhardt, and is said to have fainted in his presence and to have fled a nightclub performance with severe stage fright upon hearing a false rumor that Reinhardt was in the audience.
On a double date with his drummer, Ray meets Hattie, a shy, mute laundress. After overcoming some initial frustration due to the difficulties of communication, Ray and Hattie form an affectionate relationship. However Ray is convinced that a musician of his stature should never settle down with one woman—particularly a working-class woman like Hattie. On a whim, Ray marries socialite Blanche Williams (Uma Thurman). However, Blanche sees Ray mainly as an colorful example of lower-class life and a source of inspiration for her literary writings. She reports that Ray is tormented by nightmares and shouts out Hattie's name in his sleep.
