In Brooklyn, New York in 1969, four boys approach Minifield "Bleek" Gilliam's
Brownstone apartment and ask him to play baseball with them. His mother Lillian insists that he continue his trumpet lesson, greatly annoying him, but his father "Big Stop" fears that Bleek will become a sissy, and a family argument ensues. Bleek resumes practicing, and his friends depart. Twenty years later, an adult Bleek performs at the Beneath the Underdog jazz and comedy nightclub with his successful jazz ensemble, The Bleek Quintet. One night, his childhood friend Giant, also the band's manager, advises him to dissuade his tenor
saxophone player Shadow Henderson from grandstanding with long solos. The next morning, Bleek awakens with his girlfriend, schoolteacher Indigo Downes. During a game of catch with Big Stop, he explains his reluctance to commit to a stable romantic relationship. That afternoon, another woman named Clarke Bentancourt visits him. She suggests relieving Giant as manager; responsively, he suggests sexual intercourse (which he refers to as "mo' better"), but becomes upset when she bites his bottom lip. After betting on baseball games with his bookie Petey, Giant encounters Bleek at the club with most of the other band members, but scolds pianist Left Hand Lacey for arriving late with his French girlfriend. Later, in the office of the club's Jewish owners Moe and Josh Flatbush, he explains how the Quintet keeps the establishment profitable, and unsuccessfully attempts to renegotiate their contract. Undeterred by Petey's worries about his rising debt, Giant places several new bets the following morning. While he is visiting Shadow's residence to deliver a record that Bleek borrowed a year earlier, Shadow discloses his infidelity towards his girlfriend. In bed that night, Clarke denies Bleek's request to let her perform at the club. Bleek meets with the Flatbush brothers, who reject his demands for higher financial compensation for the other members despite the band's success, citing their current deal. That night, both ladies arrive, wearing identical red gowns he purchased for them. He attempts to reconcile with each woman, but both soon abandon him after he mistakenly calls each of them by the other's name during their alternating periods of intercourse. However, tension rises with Shadow who has feelings for Clarke. During a bicycle ride together in the park, Giant promises Bleek to manage the ensemble more effectively and efficiently, and then requests a loan to liquidate his debts. Bleek declines, and later two loan sharks apprehend Giant, breaking his fingers because of his unfulfilled payments. Bleek doubts Giant's claims that his injury stems from hitting a pothole while on his bicycle, but Left loans him five hundred dollars. When the loan sharks stake out Giant's home, Bleek agrees to house him temporarily and help him raise the money but relieves him as manager. Missing both his girlfriends, Bleek leaves messages for each, but discovers Clarke's new relationship with Shadow and dismisses him from the band. The loan sharks track down Giant at the club, drag him outside into an alley, and assault him while Bleek is performing. Overhearing and noticing the commotion, he heads outside to intervene and is assaulted to the point of hospitalization when he is smacked across the face with his own trumpet, permanently injuring his lip and ending his performing career. Over a year later, the recovered Bleek re-encounters Giant, who has become a doorman at the Dizzy Club and stopped gambling, while Clarke is now a vocalist with his former group, now dubbed The Shadow Henderson Quartet. Shadow invites him onstage, and they play together. Unable to perform correctly due to scarred lips, Bleek walks offstage, donates his trumpet to an understanding and supportive Giant, and visits Indigo's house. Indigo berates him for ignoring both her telephone calls and her requests to visit, but he implores her to marry him and save his life. Eventually, the pair marry, move in with Big Stop, and have a son named Miles, who commences trumpet lessons starting at age 5. One day, Miles, now ten years old, wants to play outside with his friends, but Indigo implores him to finish his daily lesson. However, unlike his own father, Bleek relents and permits Miles to conclude his session early. ==Cast==