1. Bull Durham (1988)
Ron Shelton’s classic comedy about minor-league baseball remains the ultimate antidote to the syrupy nostalgia and late-inning theatrics of most movies about the sport. Irreverent, wise, and richly informed by Shelton’s own experience in the lower realms of the Baltimore Orioles organization, Bull Durham sees the minors for what they are: a training ground for raw young prospects who will most likely never mature, and a purgatory for long-in-the-tooth players whose veteran stability (and consistency) makes them useful before they’re put out to pasture. Kevin Costner plays a career minor-league catcher—save for 21 sweet days in the bigs—whose only real purpose is to bring along a dumb, arrogant fireballer (Tim Robbins) blessed with more talent than Costner ever had. Over the course of this final season in the sun, Costner breaks the minor-league career home-run mark—a record he (and the movie) treats with the proper amount of ambivalence. When his protégé finally gets called up, Costner’s season (and career) ends before the summer is even over, but fortunately for him, the consolation prize to an instantly forgotten legacy is the love of a good woman. Sometimes, the greatest victories are the ones nobody sees.
2. Rocky (1976)
If Rocky Balboa beats Apollo Creed in Rocky, no way the film wins Best Picture, right? In retrospect, it already seems ridiculous that Sylvester Stallone’s modest underdog sensation beat out a murderer’s row of fellow nominees that included All The President’s Men, Bound For Glory, Taxi Driver, and Network. But key to its victory was passing off fantasy for realism: The audience could believe in the story of a determined, blue-collar pug from Philly who puts up a good fight against the best heavyweight in the world, but it’s essential that he lose on points, or else Rocky is just another sports movie, not the pseudo-authentic portrait of heart and can-do-ness that inspired five sequels. But even then, Rocky hedges its bet: The decision in Apollo’s favor is relegated to background noise, overwhelmed by Rocky’s stirring cries of “Adrian!” and the funk-tinged swells of Bill Conti’s unforgettable score.
3. The Bad News Bears (1976)
In Michael Ritchie’s gloriously profane comedy about misfit Little Leaguers, Chris Barnes’ foul-mouthed kiss-off to the evil Yankees—”You can take your apology and your trophy and shove ’em straight up your ass!”—may be the most obvious victory his Bears score in their climactic championship loss, but it isn’t the biggest. In true sporting spirit, that notch in the moral-victory column belongs to the whole team—as well as coach Walter Matthau, who, by pulling star players Tatum O’Neal and Jackie Earle Haley in favor of their benchwarming teammates, ensures that they don’t become the same kind of competitive mini-monsters as the Yankees. It also saves the formerly apathetic Matthau from becoming the kind of overly invested manager who’d slap a kid in public.
4. Bring It On (2000)
Bring It On, the poppy, peppy, and at times sharply satirical cheerleading movie that spawned a string of straight-to-DVD sequels, follows some of the usual sports-movie beats: Underdog team is good enough to win championships, underdog team’s playbook is stolen by ruthless rivals and they can’t afford to go to the Big Game, underdog team rallies to take on those ruthless rivals in the Big Game, underdog team wins the Big Game. The difference is that Bring It On isn’t told from the perspective of the underdogs, The East Compton Clovers; instead the movie follows the Rancho Carne Toros, a.k.a. the ruthless rivals. Of course, the Toros didn’t know they were so ruthless. Apparently, the Toros’ former head cheerleader, a mean girl known only as Big Red, stole the Clovers’ thoroughly awesome cheers and taught them to her squad, leading to a number of National Championship titles. When Kirsten Dunst takes over as head cheerleader, she discovers Big Red’s deception and scrambles to come up with new, original cheers for her squad. After her decision to take the easy way out by hiring a choreographer yields thousands of uninspired spirit fingers, Dunst comes up with an original cheer routine and whips her team into shape the old-fashioned way: through a hard-work montage. Sure, at Nationals (a.k.a. the Big Game) the Toros come in second behind the triumphant underdog Clovers. But considering that the Toros performed a completely original routine for the first time, and that they “brought it” against the Clovers, they scored major integrity points.
5. Tin Cup (1996)
Eight years after Bull Durham, writer-director Ron Shelton once again made his kind of sports movie, recasting Kevin Costner as another wily veteran with a chip on his shoulder, this time a backwater golf instructor who squandered his chances to burn up the professional circuit. When he plays his way into an open tournament that pits him against a former rival and tour champion (Don Johnson), Costner’s self-destructive habits get the better of him once again. Neck-and-neck with Johnson on the final hole of the U.S. Open, the prideful Costner refuses to make the smart play by “laying up” on a hole with a water hazard, and he pays the price—again and again and again, on national television. But the genius of Tin Cup—indeed, the genius of Ron Shelton—is that there’s glory in failure. When Costner finally does hit this impossible shot, well after costing himself the tournament and a future in the PGA, it offers a kind of euphoria that transcends the cold, efficient business of winning.
6. Paper Lion (1968)
In 1963, writer George Plimpton spent a few weeks at Detroit Lions training camp, posing as a candidate for third-string quarterback. He wrote about the experience for the book Paper Lion, which was made into a movie starring a pre-M*A*S*H Alan Alda as Plimpton and actual Lions (such as future movie/TV star Alex Karras) as themselves. The movie follows the book pretty closely, showing Plimpton’s struggle to fit in with his teammates—who quickly caught on to the ruse—and his trouble with learning the playbook and enduring linebacker hits. Like the book, the movie Paper Lion ends with the ersatz QB taking a few snaps from scrimmage in a preseason game, and getting his block knocked off. There’s no Rudy moment here, but since Plimpton never intended to make the team, there’s nothing tragic about Paper Lion either. The skinny Harvard man takes his licks, and fails so colossally that he entertains the crowd.
7. Kingpin (1996)
The Farrelly brothers were at their creative and commercial height when they made Kingpin, a typically ramshackle, gross-out-heavy comedy starring Woody Harrelson as a one-handed bowler who trains gifted Amish kid Randy Quaid to challenge jerky champ Bill Murray. For most of its running time, Kingpin sticks to stomach-turning (but funny) bedroom and barnyard humor, but in its climactic sequence, the Farrellys thumb their nose at sports-flick clichés. Harrelson takes over for an injured Quaid in a million-dollar tournament, and makes a difficult 7-10 split that would seem to clinch victory, until Murray fires a turkey in his 10th frame and comes from behind to win the million. (“Finally, Big Ern is above the law!” he shouts triumphantly.) Kingpin still ends on a high, though. Not only is the final showdown between Harrelson and Murray ebulliently hilarious, but in the last scenes, we learn that Harrelson’s TV exposure has earned him a lucrative condom endorsement deal. That’s the loser’s way of winning.
8. Whip It (2009)
One of the most charming things about Drew Barrymore’s directorial debut is that its scruffy underdog heroes aren’t particularly focused on victory at any cost; they’re more about self-actualization and actually having fun. When mousy Ellen Page joins a roller-derby league, her teammates tease her and haze her, but regard her from the start with a supportive big-sister camaraderie that might be impossible in a sports team that actually cared about winning. She turns out to be more driven than they are, in part because she’s trying to show up aggressively nasty rival team leader Juliette Lewis, but in the end (spoiler!) her team still manages to lose the big match. Still, this sad turn of events doesn’t break their stride: They greet it with the same “we won just by playing the game and kicking ass” attitude they’ve always had, and the same ironic yet triumphant chant they’ve relied on before: “We’re number two! We’re number two!”
9. North Dallas Forty (1979)
Based on an autobiographical novel by Dallas Cowboy Peter Gent, the shaggy satire North Dallas Forty depicts the NFL (or its fictional stand-in) as a mercenary cesspool where players are treated like disposable parts, doped up and worn out while the owners and management—the real team—sit back and rake in the dough. Nick Nolte’s bench-warming wide receiver has been ground down by years of play, to the extent that only painkillers and physical therapy can get him through a game, but he’s still determined to get back on the field. When he’s suspended for smoking marijuana, he points out indignantly that the players are shot up with harder drugs on a regular basis. But the movie makes it clear that Nolte is better off as far from football as possible. The only way to win this game is not to play.
10. Friday Night Lights (2004)
Peter Berg’s film of H.G. Bissinger’s intimately reported non-fiction tale of sports in a small town proved the missing link between the journalism of the book and the deeply felt melodrama of the (even better) TV series. But the film makes several changes to the book, most notably in how it portrays the final playoff fate of the football team at the movie’s center. In real life, the team lost in the semifinals, after their opponent came from behind to defeat them. In the film, the loss comes to the same team in the title game, but the Panthers struggle valiantly, only to succumb at the end by the slimmest of margins. It’s all okay, though, because everybody learns a lesson about how to be a better sportsman and a better man. The film ends with hope for the future, a hope built atop dashed dreams.
11. Cool Runnings (1993)
One of the few genuine underdogs to ever compete in the Winter Olympics, the 1988 Jamaican bobsled team barely needed any Hollywood gloss to tell their story. Their saga overflowed with comedy and drama, from fish-out-of-water islanders floundering in the snow to the team’s determined walk to the finish line with their damaged sled, complete with dramatic applause. So 1993’s Cool Runnings—a very loose adaptation of history, with the team’s proud military men replaced by dreadlocked goofballs like Doug E. Doug—wisely leaves well enough alone when it comes to the big finish, even though it otherwise adds completely fictional sports-movie clichés at every turn, like a redemption story for John Candy’s disgraced coach, and villainous European pretty boys who mock the scrappy heroes at every turn. As in real life, the team crashes and is forced to walk the rest of the way—although in the film, they hoist their bobsled on their shoulders (you know, for drama)—and the film’s parting message is that simply trying your best is a victory in itself. That might normally be bullshit, but in this case, such a spectacular loss really was the best thing that could have happened: Had the filmmakers waited to make Cool Runnings until after the 1994 Olympics, when the Jamaicans actually finished ahead of heavy-hitters like the U.S. and Russia (though they still only came in 14th), it’s unlikely the film would have had the same impact.