Billy Hoyle Woody Harrelson is a former college basketball player who makes his living by hustling streetballers who assume he cannot play well because he is white. Sidney Deane [Wesley Snipes] is a talented but cocky player who has beaten Billy twice.
Billy and his live-in girlfriend, Gloria Clemente [Rosie Perez], are on the run from the Stucci brothers, mobsters to whom he owes a gambling debt. Gloria’s goal is to be a contestant on the television game show Jeopardy! and make a fortune, while Sidney aims to buy a house for his family outside the rough Baldwin Village neighborhood. He proposes a business partnership with Billy in which they will hustle other players by setting them up to pick Billy as Sidney’s teammate. At first, their system is very successful, but when they unexpectedly lose a game, it turns out that Sidney had double-crossed Billy by deliberately playing badly to avenge his earlier loss to him.
Gloria and Billy go to Sidney’s apartment and appeal to his wife Rhonda [Tyra Ferrell], hoping to broker a truce. The women agree to share the money, provided Sidney and Billy team up for a major two-on-two outdoor tournament. Despite their constant bickering, Sidney and Billy win the grand prize of $5,000, largely due to Billy’s ability to disrupt his opponents’ concentration. Sidney is pleased with the outcome, but he cannot help mocking Billy about his inability to slam dunk.
Billy insists that he can indeed dunk and bets his share of the $5,000 on his ability to dunk but fails. When he tells Gloria, she leaves him. Desperate to get her back, Billy goes to Sidney for help. Sidney has a friend who works as a security guard at the TV studio that produces Jeopardy! His friend agrees to use his connections to get her on the show if Billy can sink a hook shot from beyond the half-court line, which he does. Gloria initially stumbles over sports questions but makes a comeback with a pet topic, “Foods That Begin With the Letter Q.” She wins $14,100 on her first episode.
Billy sings Gloria a song he has composed and wins her back. As Billy and Gloria discuss their future, Sidney approaches Billy for help: His apartment was burglarized and his winnings were stolen. Gloria is expecting Billy to get a steady job, but Sidney informs him that two hoops legends of the L.A. streetball scene, Eddie “The King” Faroo [Louis Price] and Duck Johnson [Freeman Williams], are playing downtown. Sidney asks Billy to partner with him to play against them. Billy agrees, offering to gamble his share. Gloria warns that if Billy gambles with her money, they are through, even if he and Sidney win. Billy sides with Sidney, feeling he must honor the obligation he owes him for getting Gloria on Jeopardy!. Gloria respectfully breaks up with Billy due to this situation. Billy and Sidney play against King and Duck and prevail, the winning point coming when Sidney lobs an alley-oop pass to Billy, who dunks it.
Billy returns home and is crushed to find that Gloria has in fact left him. The mobsters who are after Billy find him, and he pays his debts. Sidney remarks that Billy and Gloria may be better off without each other. Billy is fed up and finished with basketball hustling, and asks Sidney if he could offer him a job at his construction company, which Sidney agrees to help Billy out. The film ends as Billy and Sidney launch into another basketball argument and return to the court where they first met to play a one-on-one game, this time as friends.
