The Funniest Sport Films Ever, Arranged by Sport

Considering the ups, the downs and the drama of sports, it is hardly surprising that they are one of the central themes of Hollywood, and comedy is no different. The sports comedy genre is a rich and storied one and as the central theme, some sports are more often utilized than others. Let’s take a look at some of the best.

Ice Hockey - Slap Shot

Ice Hockey – Slap Shot (1977)

One of the greatest sports movies ever, Paul Newman shines as aging hockey player Reg Dunlop who tries to keep his team from moving to a different city by playing “old-time hockey”. The best moments might be the on-ice antics, especially by way of the Hanson brothers – but the laughs are also at times more subtle and clever.

Honourable mentions: Goon (2011), with Sean William Scott, Jay Baruchel, and Liev Schreiber, was a great hockey movie that inspired a solid sequel this year. The Mighty Ducks (1992) was a Disney movie perhaps directed more at kids, but it certainly was popular with that demographic and provided two sequels.

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Boxing – The Great White Hope (1996)

By nature of the sport’s violence and gritty culture, boxing tends to lend itself more to dramas like Raging Bull and Rocky so boxing comedies are rare indeed. The winner here, then, is The Great White Hope where Samuel Jackson plays a Don King-type promoter trying to drum up interest in a fight between a massive underdog (Peter Berg) against a dominant champ (Damon Wayans). Co-stars include Jamie Foxx, Jeff Goldblum, and Cheech Marin.

Baseball – Major League (1989)

Perhaps the sport with the most comedy contenders, we’re giving a slight edge to Major League, a great film about a hapless Cleveland Indians team whose owner fills the roster with wash-ups and screw-ups in an attempt to have an unsuccessful team in order to move to Miami. Great writing and some great performances by Charlie Sheen, Tom Berenger,  James Gammon and Bob Ueker.

Honourable mentions – Bull Durham (1988) with Kevin Costner, Susan Sarandon and Tim Robbins is another baseball comedy classic that has some serious sizzle to go along with the chuckles. The Bad News Bears (1976) (Walter Matthau, Tatum O’Neal) is perhaps the original misfits-who-overcome-the-odds sports story but is truly funny and refreshingly politically incorrect.

Dodgeball – Dodgeball: A True Underdog Story

Dodgeball – Dodgeball: A True Underdog Story (2004)

Not surprisingly, there aren’t many movies about the sport of dodgeball. This movie exalts the childhood favorite to a lofty position and has it played by the expected cast of weirdos expertly played by the likes of actors like Ben Stiller, Vince Vaughn, Stephen Root and Missy Pyle. The good guys might not win the final game but they manage to make a nice amount of money by finding somewhere that takes bets on a wide variety of sports. Perhaps a place that offers more than just sports betting but also online casino entertainment like Oddschecker, which also provides free spins and bonuses.

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Auto Racing – Talladega Nights: The Ballad of Ricky Bobby (2006)

This was Will Ferrell’s first sports-related movie and his first movie with John C. Reilly. It also Sasha Baron Cohen’s arrival party for most North American audiences. The first two play buffoonish NASCAR drivers and the movie provided us classic catchphrases such as “hammered-drunk” and “come at you like a spider monkey”. Good stuff.

Bowling - Kingpin

Bowling – Kingpin (1996)

Here’s Woody Harrelson for the third time, Bill Murray for the second and Randy Quaid for the first. The comedy is rough around the edges but the film has some of the Farrelly Brothers’ finest material. Bill Murray is at his scene-stealing best throughout and the finale is pure genius.

Honourable mention – The Big Lebowski (1998) isn’t necessarily a bowling movie but the sport does figure prominently and the movie is so good it deserves inclusion on any list of tops!

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Figure Skating – Blades of Glory (2007)

One of Will Ferrell’s best, this hilarious absurdity co-stars Jon Heder (Napoleon Dynamite), Will Arnett and Amy Poehler with cameos from some of figure skating’s biggest names. Keeps the laughs coming from start to finish.

Basketball – White Men Can’t Jump (1992)

Movies around basketball have been typically dramas and there have been some classics; Hoop Dreams, The Basketball Diaries, Hoosiers, to name just a few. White Men Can’t Jump was the first comedy that paired Woody Harrelson and Wesley Snipes – Money Train would be the second.  The two play a couple of basketball hustlers that team up to make more money.

Honourable mentions – Semi-Pro (2008) is not Will Ferrell’s finest sports comedy but does offer some laughs and also stars Woody Harrelson who is obviously an avid basketball fan in real life. Space Jam (1996) was Michael Jordan’s lone feature film endeavor and co-starred Bill Murray and other NBA superstars like Charles Barkley and Patrick Ewing. The movie was a fairly cutting edge for the time infusing live action with Loony Tunes animated characters like Bugs Bunny and Porky Pig which, obviously, means the movie is aimed at kids but they’ll definitely enjoy it.

Football – The Longest Yard (1974)

Far superior to the Adam Sandler remake in 2004, this starred Burt Reynolds at the height of his powers as a former pro forced to build a football team in prison.

Honourable mention – Jerry Maguire (1996) is more of a romance film starring Tom Cruise, Cuba Gooding Jr. (who won an Oscar for his efforts) and Rene Zellweger and gives some interesting insights into the life of a sports agent.

Golf – Caddyshack

Golf – Caddyshack (1980)

Often hailed as the funniest sports film of all-time, Caddyshack easily wins the title as funniest golf movie. Brilliantly written and directed by the late, great Harold Ramis, the laughs are endlessly provided by many sources, however, Bill Murray, Chevy Chase, and Rodney Dangerfield shine the brightest. Must see.

Honourable mention – Happy Gilmore (1996). Yes, Adam Sandler actually gets a positive mention for his portrayal as a failed hockey player who finds success on the golf course. Great cameo by Bob Barker!

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