Bleek Gilliam (Washington) is a brilliant trumpeter and overall jazz musician, but spends too much time hopping between many lovers, specifically his girlfriend Indigo Downes (Joie Lee) and up-and-coming singer Clarke Bentancourt (Williams). He also has to contend with the hardships between himself and his band, the Bleek Quintet, and his wayward manager Giant (Spike Lee), whose nasty gambling habits eventually spells big trouble for him and his client.
This film was the second to last film to star comedian Robin Harrisnote , who played Butterbean Jones. The film is dedicated to his memory.
This film provides examples of:
- Babies Ever After: Bleek and Indigo get married and she gives birth to their son a few months later.
- Betty and Veronica: Indigo is the Betty (down-to-earth, earnest girlfriend) to Clarke's Veronica (the upscale and glamorous singer).
- Beauty Is Never Tarnished: Averted, after being beaten up the the loan sharks that attacked Giant, his face is seen as swollen and discolored, as it should be after having his jaw broken.
- Book Ends: The film begins and ends with a group of boys coming to the brownstone to ask for their friend to come out and play (and hilariously enough, although each scenario is set apart by a few decades, it's the exact same boys each time although Fridge Brilliance could come into effect if those 1990 era boys were the sons of the 1960s era ones).
- Facial Horror: Twice for Bleek in the aftermath of his beating; not only is the handsome man disfigured due to the injuries he suffered, but after he finally comes back, he is initially left unable to play the trumpet as well as he did before due to his broken jaw and busted lip.
- Missing Mom: Bleek's mother died years earlier but he remains close to his supportive father.
- No-Holds-Barred Beatdown: Giant and Bleek receive a brutal one in the film's climax.
- Slap-Slap-Kiss: Bleek and Indigo's relationship due to his serial cheating. She eventually forgives him, marries him and has his baby.