White Men Can't Jump is a 1992 film starring Woody Harrelson and Wesley Snipes as basketball hustlers, and co-staring Rosie Perez as Harrelson's girlfriend Gloria Clemente. The film was written and directed by Ron Shelton and released in theaters on March 27, 1992 by 20th Century Fox.
Billy and his girlfriend Gloria Clemente (Rosie Perez) are on the run from mobsters called the Stucci Brothers, because of a large gaming debt. Sidney wants to buy a house for his family outside the rough Baldwin Hills, Crenshaw District neighborhood of Los Angeles, California, and start his own basketball coaching career.
Both players earn significant income through street basketball, and form a partnership to earn even more money. However Sidney double-crosses Billy by deliberately playing badly alongside him, making Billy lose $1700 to a group of Sidney's friends, who proceed to split the winnings among themselves. Gloria is incensed when she hears the story from Billy, and insists that they go to Sidney's place to get the money back. On the way, she tells Billy: "Sometimes when you win, you really lose, and sometimes when you lose, you really win, and sometimes when you win or lose, you actually tie, and sometimes when you tie, you actually win or lose. Winning or losing is all one organic globule, from which one extracts what one needs."
Billy is totally confused by this statement and is sidetracked by his concern about getting off the bus. Once they arrive at Sidney's place Gloria and Sidney's partner agree to split some of the money, and further agree that Sidney and Billy will team up for a major 2-on-2 tournament.
Though they initially disagree Sidney and Billy play together and win the grand prize of $5,000, largely due to Billy's ability to disrupt his opponents concentration; Billy's most notable claim is that he is in the zone, a location of frequent debate among streetballers at the time.
Sidney notices Billy's tendency not to slam dunk. Billy claims it is unnecessary grand-standing, but also believes that "...brothers (would) rather look good and lose than look bad and win." Sidney holds the view expressed in the film's title: White Men Can't Jump. Billy continues talking about how he can dunk but chooses not to. Sidney ignores him. Infuriated, Billy claims he is willing to bet his $2,500 on his ability to dunk, whereupon Sidney challenges him to dunk the ball at a local court, playing for his slice of the $5,000. In three attempts Billy fails, losing the $2,500. When Billy tells Gloria, she leaves him.
Gloria dreams of appearing on the quiz show Jeopardy!; she devotes nearly every waking moment to memorising obscure facts. Fortunately, one of Sidney's friends works as a security guard at the TV studio which produces the show. He agrees to get her on the show, if Billy can sink a half court hook shot, which he does. To begin with Gloria stumbles over sports questions (notably naming Babe Ruth as the NBA's leading rebounder), but makes a comeback with a pet topic: "Foods beginning with the letter 'q'". She wins $24,000 on her first episode. Gloria and Billy get back together.
Now it is Sidney who suffers misfortune as he is burgled and becomes more desperate for money. Billy is set to get a white-collar job and settle-down with Gloria. Despite Gloria's warning that if Billy gambles with her money "they are through", Billy decides to honor the obligation he owes Sidney; they play a final game against two hoops legends of the LA scene, The King and Duck Johnson. In a very tough game Sidney and Billy prevail, with Sidney throwing an 'over his head' alley-oop to Billy, who dunks for the winning basket.
Returning home, Billy discovers Gloria has kept her word and left him. He is initially confused: while he has won the game and the money, Gloria is gone; previously, she had stayed when he lost. Now he begins to understand the meaning of her earlier statement. He has been loyal to his friend and won the game and the respect of the L.A. pick-up scene, but has lost the girl he loves as a result.
The mobsters who are after Billy track him down, and he pays his debts. Now Billy asks Sidney to set him up with a real job. As closing credits are about to roll Billy starts arguing with Sidney over his dunk and challenges him to a game of one on one...