En 1958, Art Kane, alors photographe debutant de "Esquire", reussit un beau matin d'ete a reunir devant un immeuble de Harlem cinquante-sept musiciens de jazz. Dans la foule on reconnait Count Basie, Lester Young, Gerry Mulligan, Dizzy Gillespie, Thelonious Monk, Roy Eldridge, Sonny Rollins, Charles Mingus, Art Blakey, Art Farmer, Gene Krupa, Rex Stewart, Jo Jones, Hank Jones, Johnny Griffin. En 1989, Jean Bach, productrice de radio realisa un documentaire a partir de cette photo et retrace de grands moments de la legende du jazz.
Adam Johnson is a talented African-American jazz cornetist, plagued by ill health, racism, alcoholism and a short temper, as well as guilt over the deaths years before of his wife and child. The result is a caustic personality that wears even on those who care the most about him, such as his best friend Nelson, and Vincent, a young Caucasian trumpeter whom Adam mentors. Arriving unexpectedly at his New York home drunk after walking out on his jazz quintet, Adam finds prominent Civil Rights worker Claudia Ferguson and her grandfather, Willie, who is himself a well-known jazz trumpeter, in his apartment. The two have been given access to the apartment by Nelson, but despite having authorized this, the drunken Adam is rude to both, that including making a vulgar pass at Claudia.
Emmet Ray (Sean Penn) is a 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.
The film follows a group of jazz musicians in the 1960s who play in small clubs and face constant financial hardships. Of the group, only one of them will go on to achieve success.
Dale Turner, a famous African-American tenor saxophone player in Paris in the 1950s is befriended by Francis, a struggling French graphic designer specialized in film posters, who idolizes the musician and who tries desperately to help him to escape alcohol abuse. As he succeeds, the budding friendship they develop changes their lives forever.