“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 and losing is all one big organic globule from which one extracts what one needs.” —Rosie Perez, White Men Can’t Jump

The quote above, from the wise, tempestuous Gloria Clemente in White Men Can’t Jump, is the closest thing to a thesis statement that writer-director Ron Shelton has ever written. For my money, he’s made the best baseball movie (Bull Durham), the best golf movie (Tin Cup), and this, the best basketball movie, in part because he doesn’t view winning and losing like everyone else does. To the extent that he’ll allow himself the “big game” moments that define virtually every other sports movie, Shelton cannot abide victory as a have-it-all triumph where the crowd roars and the hero is carried off on his teammates’ shoulders. Sports themselves may be a pursuit where “winning isn’t everything, it’s the only thing,” but for Shelton, movies needn’t be the same mechanism. Too much happens off the scoresheet. 

An early example of the Ron Shelton touch comes in a Bull Durham scene where Crash Davis (Kevin Costner) advises young fireballer Ebby Calvin “Nuke” Laloosh (Tim Robbins) to relax on the mound and stop trying to strike everybody out. “Strikeouts are boring,” he says. “Besides that, they’re fascist. Throw some ground balls. It’s more democratic.” Shelton has an allergy to athletes with killer instincts, and champions those who stumble through life more modestly, picking up wins and losses, and maybe a little perspective. Bull Durham ends midway through the season, with Nuke getting called up to the majors and Crash consequently losing his purpose as a minor-league veteran assigned to whip the kid into shape. His consolation is retiring with the minor-league home-run record and walking off with the only woman (Susan Sarandon) who even cares about the achievement. In the brilliant Tin Cup finale, Costner’s big triumph on national television doubles as a meltdown that underlines why a man of his talent could never make it as professional golfer. 

White Men Can’t Jump offers two Shelton heroes for the price of one, street-ball hustlers who exist on the fringes of the sport, making the rent one pick-up game at  a time. Sidney Deane (Wesley Snipes) and Billy Hoyle (Woody Harrelson) are among the legions of basketball players who, due to lapses of talent or temperament, simply weren’t good enough to make it in the pros. Shelton doesn’t account for how Sidney got to hustling on the courts of Venice Beach and greater Los Angeles, and Billy’s backstory is mumbled out in embarrassment, something about playing college hoops in Louisiana, which didn’t work out. White Men Can’t Jump is a vastly entertaining movie, funny and sexy and full of memorable trash talk, buddy chemistry, and high-stakes/low-stakes action, but there’s always that feeling that Sidney and Billy are living in that “organic globule” where wins and losses are ambiguous, and always contingent on factors off the court. 

Before the first “Your mama” joke is even dropped, Shelton establishes the world of White Men Can’t Jump as the minor leagues without the league, folded into a beach landscape of bodybuilders and street musicians, with players who stake whatever loose cash can be stuffed into their sweatsocks. Sidney is the king of this particular pond (“I don’t mean to brag… but I’m the greatest!”), but he cobbles together a living from off-the-books construction jobs, too, and returns to a crummy Crenshaw apartment called Vista View. (His wife Rhonda, played by fiery Tyra Ferrell, says “There ain’t no vista. There ain’t no view. And there certainly ain’t no vista of no view.”) Billy has it considerably worse, lodging with Gloria in a $29/night motel while dodging the “Stucci brothers,” two-bit gangsters looking to collect the $8,000 he owes them for having too much pride to throw a game. Billy has a particularly bad penchant for losing when he wins. 

But athletes are, by nature, more prideful than pragmatic, which is why Sidney and Billy are still chasing glory on the court instead of reaching the hard conclusion that basketball isn’t going to work out, and it’s time for a more sensible living. Meanwhile, they’re running cons around the city, with Billy effectively mining the assumption that white players—particular the brand of Middle American dork Harrelson has played since Cheers—are too slow and clumsy to go with the two-on-two flow of street-ball. After conning Sidney on his home turf and returning triumphant to Gloria, bearing takeout food and a wad of cash for the Stucci jar, Billy is surprised to get an offer from his vanquished foe to work the courts around the city in the lead-up to a two-on-two tournament with a $5,000 grand prize. It’s an uneasy partnership to say the least, rife with arguments over aesthetics (“You’d rather look good and lose than look bad and win,” Billy tells Sidney), the music of Jimi Hendrix, and competing egos, especially when it comes to Billy’s hyper-sensitivity about his girlfriend. Then Sidney turns the tables and cons Billy right back, leading to a dejected Billy declaring, “I don’t hustle with people who are dishonest.” 

The best scenes in White Men Can’t Jump nearly all involve Perez’s delightfully pugnacious Gloria, who works hard at two projects throughout the film—making a solid man out of Billy, and studying to appear on Jeopardy!—and only succeeds at one. The second-best scenes find Shelton delving into the street-ball subculture with the same eye and ear for the colorful and the profane that he brought to Bull Durham a few years earlier. The language is all macho aggression: Some of it is tactical, intended to psych opponents off their game, and some of it is chest-thumping disses for their own sake. As self-destructive as he is off the court, Billy’s verbal game is as elevated as Sidney’s. Not only does he get the best “your mama” joke in the movie—“[Let’s] gather up all these bricks and let’s build a shelter for the homeless, so your mother has a place to live”—but deploys it both to agitate his future opponents and embarrass Sidney for the sport of it. There’s an element of “white guys drive like this/black guys drive like that” comedy that’s very 1992, but it’s countered by a frankness of racial dialogue that’s absent now, but was present in studio films like this and Spike Lee’s Jungle Fever from the year before.

The other 1992 element of White Men Can’t Jump is the buddy-movie dynamic between Sidney and Billy, though Shelton makes it more sophisticated than other movies where rivals have a love/hate relationship before landing on grudging respect and friendship. We learn as the movie goes on that Billy is flat wrong about his race-based assumption that Sidney would rather look good and lose than look bad and win, though style is certainly part of his game. In the Shelton style, both men are flawed in ways that have kept them—and will forever keep them—from making the big time. But throughout the course of the film, a distance opens up between Sidney’s hidden pragmatism and Billy’s foolishness with money and women. Sidney is upwardly mobile, cobbling money from multiple jobs, and if it takes scamming Billy to do it, hey, “You either smoke or get smoked.” Billy cannot handle having his ego questioned, and it costs him time and again—on his debt to the Stucci brothers, on a side-bet with Sidney over whether he can dunk, on a game against the fabled duo of “The King” and “Duck” that Gloria’s speech on winning and losing keenly foreshadows. Sidney understands Billy far better than he understands himself; for all his wonderful swagger in the basketball scenes, Snipes is just as good in quieter moments, like reaction shots where he sees Billy’s destiny far clearer than his friend does. 

“He’s full of shit and he’s a good guy,” says Billy of Sidney, confused about his own affection for his partner, just before learning Sidney’s taken all of his money on a con, and will take all of his money again on a bet later on. In the organic globule of White Men Can’t Jump, this is what counts for friendship and fair play, and the rousing finale sticks Billy in the position of choosing Sidney and the game over love and stability. Guys like him are doomed to snatch defeat from the jaws of victory. And while they show up in sports—and life—all the time in the real world, virtually the only time they show up in sports movies is when Ron Shelton sits down behind a keyboard.

Tune in tomorrow for Noel and Tim’s Forum on White Men Can’t Jump’s refreshingly confrontational race-based humor, the protagonists’ limitations, and the movie’s powerful opening 10 minutes. And on Thursday, the staff and friends run down the scores on basketball movies in our periodic By The Numbers feature.