White Men Can't Jump is an Odd Couple comedy from 1992 starring Wesley Snipes, Woody Harrelson, Rosie Perez and Tyra Ferrell. It's about two basketball hustlers, Sidney Deane (Snipes) and Billy Hoyle (Harrelson) who work the playground courts of Los Angeles. When Billy ends ups hustling Sidney, Sidney proposes the two of them team up to play in a tournament and to hustle other players as a warm-up beforehand. Written and directed by Ron Shelton of Bull Durham and later, Tin Cup, the movie boasts his signature snappy dialogue and a real handle on athletes and their egos. Also bizarrely got an In Name Only video game adaptation for the ill-fated Atari Jaguar.
Bittersweet Ending: Billy and Sidney have gotten enough money so Sidney can move his family to a better neighborhood and Billy can finally pay off the Stucci brothers; not only that, but Billy and Sidney finally seem to be back on good terms. However, Gloria has most likely left Billy for good.
Book Ends: The singing group at the beginning of the movie shows up at the end.
Bookworm: Gloria, constantly pouring over almanacs.
Catch Phrase: "It's hard goddamn work making you look this bad!"
Hoist By Their Own Petard: When Billy and Sidney lose $1700 during a hustle they initiated, which just makes their tenuous money situations even worse. Subverted when Gloria sniffs out that Sidney actually just hustled Billy by playing bad on purpose.
Hustler: Both Billy and Sidney are somewhere between this and Con Man.
Nice Job Breaking It, Hero: Billy does this three times. First, this is the entire source of the problem between him and the Stucci brothers; they paid him to throw a game, but one of the opposing players insulted his ability, he took offense, and ended up winning a game he was supposed to lose, which made the Stucci brothers upset, and now he's on the run. Secondly, after Billy and Sidney have won the tournament, Sidney insults his jumping ability, so Billy bets Sidney his winnings that he can, in fact, dunk the ball; naturally, he loses, and this causes Gloria to break up with him. Finally, after Billy and Gloria have gotten back together, and Sidney's apartment has been robbed, Sidney comes up to Billy asking him to play a game with him so he can win enough money to move. Billy leaves, which gets Gloria upset because Billy had promised to stop playing (plus he used her Jeopardy winnings as collateral), and she ends up leaving him for good.
Sidney gets a pretty big one himself. Billy probably would not have lost Gloria if Sidney had done a better job explaining what was going on. If he had told her about the burglary and wanting his family out of Vista View, she would likely have cut him a break. Sidney instead pressures him into taking the game against King and Duck, and then he clams up and watches Billy hang himself by going against the very advice HE gave him to reconcile with her. Even if Sidney was newly desperate, this makes him look like a pretty big Jerkass. His throwing Billy's choice back at him in the pentultimate scene doesn't help either.
Obfuscating Stupidity: Billy's entire act; he dresses up in goofy clothes, does exaggerated workout routines and generally acts like an idiot so people will immediately think he isn't much of a player.
Gloria: 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 mechanism, from which one extracts what one needs.