The 11 Best Sports Films of the Last Two Decades

The 11 Best Sports Films of the Last Two Decades
Mark Wahlberg weighs in in "The Fighter".

Since 1991 --after such great 1980s sports films like Hoosiers, The Natural, and Chariots of Fire-- a lot of excellent film work has hit the screen. The best films often deal not only with the sport featured but the lives of every day people across all walks of life.

I've seen a lot of sports films and there are probably plenty I still need to see more. Besides, I can't narrow down a century of film into 10 best sports films, and couldn't pick only ten for the last 20 years.

But here's the eleven best I've seen in the last two decades.


11. Dogtown and Z-Boys (2001)

A dozen bored California surfers, mostly Venice kids, not only reinvent the skateboard but remake a once-forgotten-about suburban fad from the 1950s into an action sports revolution.

Narrated by Sean Penn, Dogtown depicts life in the more rundown “locals only” beach communities circa 1974, which consisted of mostly of surfing in the early morning tides and loitering. The Zephyr Team (aka Z-boys) spend one summer combating the boredom by building their own boards with the help of Jeff Ho, a surf shop owner. After  re-emerging in skateboarding competitions in LA, they transfigure it all into their own scene; one that spawns a generation of skateboarders like Tony Hawk and the creators of the X-Games.

Dogtown puts chronological perspective into skateboarding's up-from-the-bootstraps history that you never knew it had.


10. Jerry Maguire (1996)

Jerry Maguire, played by Tom Cruise, is a hot shot sports agent who gets fired from his job and questions everything he lives, says and believes.

While the film peers into exciting world of sports celebrity, it delves into Maguire’s vane superficiality as it unravels in the wake of his own personal choices.

This Cameron Crowe film not only was Oscar-nominated, but also springboarded the careers of Renee Zellweger, Bonnie Hunt, and Cuba Gooding, Jr., who himself won an Oscar for Best Supporting Actor.

Moreover, this film familiarized us with terms like “Qwon”, “Show Me the Money”, and with precocious toddlers in glasses. Jerry Maguire is curriculum 101 film for any sports enthusiast.


9. Fever Pitch (The 1997 BBC version)
A football-obsessed school teacher has spent the last 20-some years viewing life through the one lens: the day-to-day of his favorite team, north London's Arsenal Football Club. Having sublimated the grief of his parents’ divorce through English Football, he views every week of his life as another football match in pursuit of fortunes always hiding.

Before they were kings: Colin young Firth as a young soccer nut

Colin Firth, who usually plays the archetypical sullen Brit, is resounding as author Nick Hornby’s autobiographical noncommittal single man who’s really just a lad grown up. Hornby’s character then grows smitten a prim and proper lit teacher who dislikes him at first but warms up to his enthusiasm for life in general.

Fever Pitch is a nice portrayal of an irrational sports lover reluctantly coming to terms with the fact that, to the rest of the world, there are more important things than Saturday’s game.


8. Invincible (2006)

I’ll have to admit bias on this one. Not so much because I grew up a Philadelphia Eagles fan, but because I am a huge fan of the underdog. Even better, Invincible is based on a true story of a man walking on to his hometown NFL team.

In the drab and recession-laden mid-1970s, the lowly Philadelphia Eagles are so bad that their new head coach, Dick Vermeil, announces tryouts open to the public on live TV. While every Eagles-obsessed yahoo in town lines up, one standout athlete, a 30 year old bartender named Vince Papale is good enough to go pro.

Papale grapples not only with the challenge of just making the cut day-by-day, but also with his new role as a star and outcast in his own microcosm of working class Philadelphia.

Greg Kinnear and Mark Wahlberg are both convincing, and even if you’re a Giants or Cowboys fan, you will be inspired to root for Vince as the underdog that delivers on game day.


7. Hoop Dreams (1994)

The documentary Hoop Dreams starts off in the late 1980s when two Chicago boys are scouted for their basketball talents. One gets a scholarship to a prestigious private high school in the suburbs while the other roughs it through the public school system and an unstable home life. William and Arthur, both inner-city kids, dream of becoming NBA superstars like their idol, Chicago’s own Isaiah Thomas.

Following the kids over four years of life in high school and pursuit of college, the makers of Hoop Dreams weave together an eye-opening story about inspiration and triumph amidst the difficulties of city life and scant opportunity.

The film, which Roger Ebert regards as one of the best films he ever saw, is a refreshing look at sport on the street, removed from the glitz, glamour and marketing mash up of the professional big leagues.


6. Don King: Only in America (1997)
The great Ving Rhames plays a local Cleveland bookie and some time ex-con maneuvering his way to the top of the nascent and dynamic world of pro boxing.

Rhames, best known for his role as Pulp Fiction’s gang thug Marcellus Wallace, plays a different type of tough guy and hustler in the form of an animated and verbally combative Don King; a persona he nails. Only in America also cameos Jeremy Piven and the late Bernie Mac and soul singer Lou Rawls.

Rhames as King, signing George Foreman to fight Muhammad Ali.

For as much as other films like Any Given Sunday and Jerry Maguire have endeavored to depict the perceived evil of sports promoters, Only in America does so not by belaboring its players as bad people. Rather Don King’s character is flamboyant, human, and so exciting that, as he puts it “If you didn't have Don King, you'd have to invent him.”


5. Cinderella Man (2005)

In the last few decades there has been a drought of good films about the Great Depression that weren’t about bootleggers and mobsters. Cinderella Man recounts the true story of an on-his-way-out boxer and longshoreman whose family is down to their last penny.

James Braddock’s unlikely last hope is his boxing career. While slumming it to the dock every single day to find scarce work, he hides his injuries to take a crack at the younger up-and-coming professional fighters at first just for the pay. But his stamina and heart, and ability to withstand a beating (both in life and boxing) gifts him with a few knockouts and an underdog’s chance to challenge the great killer champion Max Baer for the title.

If you ever have spent a day of your life feeling useless or defeated, watch this film and it will put your attitude and your head straight.


4. The Fighter (2010)
Like Rocky, The Fighter tells the story of a boxer from the rough side of the inner city, taking a few last punches toward the big dream. But this one too, like Cinderella Man, is based on a true story.

Micky Ward, played by Mark Wahlberg, is a working class Irish-American boxer from Boston who has spent much of the late 1980s and early '90s punching above his weight in ruddy sports complexes and nothing bouts put together by his mother and manager. His misanthrope half brother, Dicky Eklund (played by Christian Bale) acts as his trainer but shows up hours late for practice sessions. Ward lives a humdrum life boxing on the side while paving roads in the city. Dicky was once considered the "Pride of Lowell" for having reached professional boxing's pinnacle, but since has fallen into a life of petty crime and crack addiction.

Ward meets his girlfriend, played by Amy Adams, and she encourages him to stand on his own feet and stop wasting time. Eventually Ward works his way toward the top while balancing the push and drive behind him from his new lady and the everyday mania of his toxic family.

Bale and Adams garnered Oscar awards for their roles in The Fighter, while Wahlberg, who had a hand in directing and casting, shines as an underdog that pulls it all together, making himself into a masterpiece from the rubble.


3. Big Fan (2009)
So you think you're a crazy sports fan? Without a doubt comedian Patton Oswalt, has you and all of your wildest tailgate pals outdone in his portrayal as Paul Aufiero, a lonesome, obsessed New York Giants fan. Oswalt shows he's more than just a punchline wizard here, slinging acting chops and studied creepiness that are reminiscent of Oscar winner Robin Williams in the 2002 psychological thriller "One Hour Photo".

Probably in his late 30s, Aufiero attends every Giants home game and tailgates but can only afford listen on a car radio from the Meadowlands' parking lot. He lives on Staten Island with his elderly mother and works the night shift at a garage. In his spare time he calls into local sports radio to talk football and reads his prepared pro-Giants diatribes about the dumb "cheese steak heads" in Philly and his favorite player, Giants linebacker Quantrelle Bishop.

Patton Oswalt plays a sports fan who really needs to get a life in Big Fan.

One day Paul and a friend spot Bishop in Staten Island and follow him into Manhattan, only to get beat up later by the Giants' star and his entourage of thugs. After waking from a coma he struggles to comprehend what happened under pressure from his brother, a personal injury lawyer, to sue the now-suspended NFL all-pro. Suffering ridicule from locals and being taunted by a Philadelphia Eagles fan, played by Michael Rappaport, who also calls into the New York radio show, Paul stages the most anti-social and far reaching stunt of his life.

Big Fan is an excellent, if extreme, illustration of how important major sports has become to much of America, in both an entertaining an disturbing fashion.


2. Seabiscuit (2003)

In another riches to rags 1930s-era film, a half-blind jockey too tall and a horse too small, wild, and lazy team up to recreate themselves as the new juggernaut in horse racing.

Based on another true story, the film starts with a narrative by the documentary voice of great historian David McCullough. In the way that Sputnik caused Americans to fear communism and the rise of the Soviet Union in the 1950s, Seabiscuit, a mere race horse, inspired an America sorely beaten down by The Great Depression. No one exactly knows how this horse achieved what it did, but the story is all about heart.

Tobey Maguire does well as an unsure and improbable horseback while Jeff Bridges plays the race team’s promoter and personal coach in an enthusiastic style reminiscent of champion football man Vince Lombardi. It's  another must-see whether or not you care about sports or horse racing at all.


1. Invictus (2009)

Invictus is, in my view, the best sports film since Rocky, which I believe was the greatest sports film ever made. Invictus is as good as Chariots of Fire, better than Raging Bull, and blows Hoosiers out of the water.

You need know nothing about rugby nor South Africa to dig in and enjoy this movie. Clint Eastwood directs, as Matt Damon, perhaps for the first time in career, acts so well that you forget you’re watching Matt Damon.

Damon portraits François Pienaar, the captain of South African Rugby. His team is talented but in wholesale disarray; listless, unmotivated and evocative of the Bad News Bears. Meanwhile, the nation’s black rugby fans cheer not for South Africa but for England.

At the same time, newly elected Nelson Mandela wrestles with the task of reuniting the country amidst reconciling black aspirations with white fears.

With South Africa hosting the soon-approaching World Cup, the rugby team’s management is fired while the new black government coalition tries to change the team’s mascot and team name, The Springboks, in attempt to erase all memory of Apartheid.

Mandela quietly calls on captain Pienaar to reset the tone and prepare the Springboks for the unlikely feat of winning the World Cup at home and uniting the nation.

Invictus gets its name from a poem by William Ernest Henley that Mandela holds dear as something that made him stand up when, imprisoned for 26 years, “all he wanted to do was lie down”. Like the poem, which speaks of the ability to take responsibility for one’s destiny, the film tells the story of South Africa’s steps forward in the work-in-progress of setting free the nation, both psychologically and sociopolitically from its checkered past.

Invictus has so many important facets at work in a brilliant, exciting, but well-tailored storyline, that you’ll digest it for days.


Honorable mentions (of films since 1991):
The Blind Side, Green Street Hooligans, Rudy, Rocky Balboa, Bend It Like Beckham, A League Of Their Own, Murderball, Searching For Bobby Fischer, Radio, Remember The Titans, The Rookie, Unforgivable Blackness: The Rise And Fall Of Jack Johnson, Million Dollar Baby, Dodgeball.

Follow @MySportsComplex

Andy Frye lives, breathes and writes about sports and here at ChicagoNow.

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  • I like your list. Hoop Dreams would have been at the top for me. But since Invictus is my favorite poem. Thumbs Up.

  • In reply to Evan Moore:

    Thanks, sir.

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