Standing on a 1969 Brooklyn, New York, sidewalk, four African American boys call to Bleek Gilliam to join them for a baseball game. Bleek’s mother, Lillian, orders him to tell his friends he is practicing his trumpet and send them away. The boys, including a small kid nicknamed “Giant,” call Bleek a “sissy” and leave. When Bleek complains how much he hates the trumpet, his father, “Big Stop” Gilliam, promises to throw a baseball with him after practice. Twenty years later, Bleek plays trumpet in his own group, The Bleek Quintet, at the Beneath the Underdog jazz and comedy club. Bleek’s boyhood friend, Giant, who is now his manager, suggests that Bleek fire Shadow Henderson, the group’s tenor saxophonist, because he hogs the stage. When Bleek warns Shadow to stop grandstanding, tension grows between them. In the morning, Bleek awakens Indigo Downes, one of his girl friends, and hurries her out the door. Donning his New York Yankees shirt and a baseball mitt, Bleek tosses a ball with his father. Big Stop Gilliam asks which of Bleek’s girl friends he likes the best, and warns him not to bring any babies into the world until he finds out. At home, Bleek cleans his trumpet and practices until Clarke Betancourt, another girl friend, rings his door buzzer. Bleek admonishes Clarke for arriving an hour early, because she knows he practices every day until two p.m. She criticizes the way he over-regulates his time, but Bleek reminds her that music comes first in his life. Clarke wonders why, if Bleek loves music so much, he keeps the incompetent Giant as his manager. When Bleek wants to make love, Clarke insists that what Bleek does has nothing to do with love, only sexual gratification. As they have sex, which Bleek calls “mo’ better,” Clarke bites his lower lip, and Bleek becomes angry because it might affect his trumpet playing. Meanwhile, Giant bets on baseball games with his bookie, Petey. Elsewhere, in the Beneath the Underdog office, Jewish owners Moe and Josh Flatbush discuss last night’s receipts. Moe declares that he trusts only numbers, because numbers, unlike people, do not lie. That night, as mostly white fans line up outside the club, Giant asks the bouncers, “Eggy” and “Born Knowledge,” why they keep customers on the sidewalk until the last moment. Eggy explains that having a crowd outside generates excitement and advertises success. As pianist “Left Hand” Lacey arrives late backstage with his girl friend, other band members berate him for bringing a woman into their dressing room. Lacey accuses them of criticizing her for being white. While the Bleek Quintet performs in front of a full house, Giant tells the Flatbush brothers it is time to raise the musicians’ pay, because the club is making a lot of money. The owners remind Giant that he signed a contract, and they never renegotiate. When Bleek goes home after the show, Indigo Downes waits on his doorstep. She does not like going to clubs, and would rather listen to records at home. Indigo asks what Bleek would do if he could no longer play music, and he says he would curl up and die. At a breakfast café the next morning, Petey, the bookie, reminds Giant that his bets were losers and refuses to take any new ones until he pays his considerable debts. Giant goes to Bleek’s apartment and announces he is going to demand more money from the Flatbush brothers, or else. Later, as Bleek and Clarke have sex, she asks why he refuses to let her sing with his group, because Shadow has told her she has a great voice. Bleek gets out of bed and composes a new tune, refusing to listen to Clarke’s complaints. At the club, Bleek’s band members demand a raise, and if Giant cannot deliver, they want new management. Giant gets a backstage telephone call from Petey, demanding immediate payment. During a break, when Bleek tells the Flatbush brothers he needs more money, they inform him that since Giant negotiated the quintet’s original deal, they cannot renegotiate with him. However, if their cousin took over as the group’s manager, maybe a new arrangement could be possible. On the other hand, if Bleek breaks his contract, the Flatbush brothers will sue him. Sitting at the bar, Giant watches Clarke and Indigo walk into the club only moments apart, wearing identical red gowns Bleek bought them in France. He alerts Bleek backstage. Shadow Henderson sits at Clarke’s table, asks why she keeps seeing Bleek, and tells her he wants her to sing in his band as soon as he puts it together. Seeing Clarke talking with Shadow, Bleek slips over to Indigo’s table to divert her attention, but Indigo has already seen Clarke and realizes that Bleek is having sex with her. Bleek joins Clarke as soon as Shadow leaves her table, but she is angry that Indigo is there. Backstage, Bleek relinquishes Clarke to Shadow if he wants her. In the days after, as Bleek alternately makes love to Clarke and Indigo, the two women become indistinguishable. Clarke gets angry when he accidentally calls her Indigo, and Indigo is indignant when he calls her Clarke. Each woman asks why is he still having sex with the other, but Bleek ignores their anger by playing his trumpet. Soon, both women leave him. During a bike ride in the park, Giant promises Bleek to do a better job as manager. When Giant returns to the neighborhood, Madlock and Rod, two enforcers, grab him and break some of his fingers. With his hand bandaged, Giant tells Bleek he hit a pothole on his bike. He asks everyone if he can borrow money, and all except Left Hand turn him down. He loans Giant several hundred dollars. Bleek laments that only white and Japanese people come to hear the combo play jazz, because African Americans have turned away from their own music, but Shadow blames the problem on Bleek’s refusal to “play to” a black audience. Meanwhile, Giant goes to pay Petey the money he owes, but changes his mind at the last minute. Shadow visits the record store where Clarke works, but when he tries to buy several compact discs, his credit card is declined. He confesses he really came to see her. That evening, after the show, Giant joins Bleek outside and asks to move in with him for a while. Bleek agrees to help raise money to pay Giant’s bookie, but he will have to get help for his gambling problem. Bleek also fires him. Later, Bleek telephones Indigo and leaves a message on her answering machine. She listens without picking up. Elsewhere, as Shadow makes love to Clarke, Bleek telephones and leaves a message. Clarke’s first reaction is to answer the phone, but Shadow convinces her to let Bleek talk to the machine. At the club, Giant tells Bleek that Shadow is having sex with Clarke, and when Shadow arrives and wants to talk about money, Bleek hits him. The other band members separate them. Madlock and Rod grab Giant in the bathroom and drag him into the alley. Bleek sees them from the stage, takes a break, and goes outside. The enforcers have beaten Giant, and as Bleek tries to pull them away from his friend, they beat him unconscious with his trumpet. Bleek’s dad visits him in the hospital, and recalls how proud he was when Bleek, as a boy, stood his ground in fights. While recuperating at home, Bleek listens to John Coltrane albums and remembers the days he courted Indigo. A year later, Bleek goes to the Dizzy Club where Clarke Betancourt is singing with The Shadow Henderson Quartet. Walking with a cane, Giant greets Bleek outside. He has stopped gambling and works as the club doorman. The quartet is Bleek’s old band. Shadow brings Bleek to the stage, but when he tries to play a solo, his upper lip, scarred from the beating, ruins his performance. He hurries out of the club, gives his trumpet to Giant, and walks away. Giant promises not sell the horn because Bleek will someday want it back. When Bleek goes to Indigo’s house, she berates him for not returning her telephone calls and refusing to let her visit. He recounts a story about a married couple on a falling airplane who had sex in their final moments because they loved each other. Bleek asks Indigo to marry him and save his life. She fights, then embraces him, and he carries her upstairs. Giant, Shadow, the other members of the band, and Clarke all attend Bleek and Indigo’s wedding. The couple moves in with Big Stop Gilliam and have a son named Miles. At age five, Miles begins practicing with the trumpet. When neighborhood boys come to the window wanting to play ball, Indigo sends them away because Miles has to practice.