“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.”
These are the words of Gloria Clemente, the tempestuous sage played by Rosie Perez in White Men Can’t Jump. And they are also the words of Ron Shelton, who sees sports as one big organic globule from which he can extract comedy, romance, and a little bit of philosophy. Shelton’s experiences as a minor-league ballplayer informed the wonderful details of farm club life in his 1988 breakthrough film, Bull Durham, but his perspective on failure is what sets him apart. Where other sports movies are about inspirational figures and miraculous comebacks, his movies are about men whose personal shortcomings prevent them from making it big. Bull Durham ends before the season is even over, with Kevin Costner’s journeyman catcher quietly retiring after helping a more talented younger player make the bigs. Shelton’s great Tin Cup ends with Costner’s never-was golfer wrapping up a tournament run with an epic meltdown that seems like a loss, but is really a win. And White Men Can’t Jump ends with a streetball triumph that seems like a win, but is really a loss.
In any sport, there are plenty of never-wases—athletes who tethered themselves to dreams of professional glory, but didn’t have the talent or the temperament or the good fortune to make it all the way. When Costner’s catcher talks about his brief stint in the majors on the team bus, his teammates gather around to hear stories of baseball cathedrals where new balls are used for batting practice. Most of them are not going to see even that much action, but this is all they’ve ever thought about doing, so what could possibly be their Plan B? In White Men Can’t Jump, we don’t learn the backstory of Sidney Deane, the preternaturally confident street ball king played by Wesley Snipes, but we do discover that Billy Hoyle, the sharpshooting geek played by Woody Harrelson, did some college hoops in Louisiana. It doesn’t seem like he was scouted. Perhaps he didn’t even finish school. Whatever the case, he didn’t make it.
And so now, Sidney and Billy are working the courts like Paul Newman in The Hustler, running a con where Sidney pretends like Billy is a stranger and has his opponents choose anyone around to be his teammate. They invariably choose Billy because he’s a goofy-looking white guy they assume they can run off the court. The scam works, but there’s no honor among thieves in this world, so Sidney has no moral reservations about running his own con on Billy and taking him for every dime. And Billy, who’s terrible with money, find his own ways to blow his newfound winnings, like betting Sidney that he can dunk a basketball.
One of the grace notes of White Men Can’t Jump is its attention to the practicalities of the hustle, which often fall to Sidney and Billy’s significant others—Sidney’s wife Rhonda, played by Tyra Ferrell, and Billy’s girlfriend Gloria, who’s hard at work studying for her own dream of appearing on Jeopardy. There’s a sense that both men love basketball too much to leave it behind, but only Sidney has the skills to do something else for money, serving as a contractor on various home construction projects. Billy has no other skills, and can’t get beyond his current cycle of losing any money he wins, and begging for second chance after second chance from Gloria, who loves him, but also considers him a project she might have to abandon.
The moral of Ron Shelton’s movies is those who take from the sport are better off than those who let the sport take from them. Costner’s characters in Bull Durham and Tin Cup never come close to realizing their ambitions as athletes, but they have the good sense to appreciate the wisdom, friendship and love they’ve gained from their experiences and they’re content to leave the dream behind. Sidney Deane seems like he’s getting close to that moment, too: He and Rhonda want to move away from Vista View apartments—where there ain’t no Vista, there ain’t no Views, and there sure as hell ain’t no vista of no views. Basketball is a means to an end for him, and there’s a sense that he’ll find his way there. Billy Hoyle, on other hand, knows no other life but the hustle. For him, a win is almost always a loss in disguise, because it’s the precursor to a mistake he can’t stop making. He’s a lovable loser. But, in the end, he’s not just played the chump. He is the chump.