With COVID-19 shutting down schools, businesses and seemingly everything else across the country, both movies and sports are experiencing an unprecedented hiatus. This is as good a time as ever to stay home and try to enjoy both sports and movies as best we can and the best way to do that will be combining the two. We’ve been breaking down the top choices for films to enjoy based on each major sport, starting with baseball and today we’ll be talking about my top 10 choices for the greatest sports comedies of all time. Feel free to share your own personal favorites as well, there is plenty to discuss.
10. Blades of Glory (2007)
When a rivalry between the world’s best men’s figure skaters, sex addicted, improvisational Chazz Michael Michaels played by Will Ferrell and germophobic, precise Jimmy MacElroy played by Jon Heder, breaks into a fight on the awards platform, they’re banned from the event for life. Three years later, the desire for a gold medal and a careful reading of the rules lead them to compete as skating’s first male-male pair. Can they overcome mutual dislike, limited time to prepare, their coach’s secret past and the dirty tricks of their main opponents, the Van Waldenberg siblings?
Ferrell and Heder and the rivalry between their two characters are obviously the focus of Blades of Glory but like with many sports comedies, I think it comes down to the quality of the supporting characters. Craig T. Nelson does a phenomenal job playing the two stars’ coach and Will Arnett and Amy Poehler stand out as the Van Waldenberg siblings. Jenna Fischer and William Fichtner have big roles as well and this mix of talent thrown into the film’s silly premise make for a fun time at the movies.
9. Semi-Pro (2008)
In 1976 in Flint, Michigan, Jackie Moon’s, played by Will Ferrell, American Basketball Association team languishes in last place with few fans in the seats. Jackie dreams of a merger with the NBA. A tough-minded point guard named Monix, played by Woody Harrelson, is at the end of his career after playing for the champion Boston Celtics but accepts a trade to Flint to be close to Lynn, the love of his life played by Maura Tierney. Clarence “Coffee” Brown, played by Andre 3000, dreams of stardom. He’s the Tropics’ best player but doesn’t value teamwork. When the trio learns that a merger with the NBA is in the works that won’t include the Tropics, they pull the team together to try to achieve the impossible. Can dreams come true in Flint?
Semi-Pro often flies under the radar when discussing sports comedies. While it’s not Ferrell or Harrelson’s best sports movie, they still work together great in Semi-Pro to give us plenty of laughs. Andy Daly and Will Arnett are following the team throughout the season as the Tropics’ radio crew and provide jokes from the sidelines as well. The film can get a bit silly from time to time but finishes strong in the final game of the season when the Tropics make their mark on the game of basketball forever in the Flint, Michigan Mega Bowl.
8. The Longest Yard (2005)
Paul Crewe, played by Adam Sandler, was a revered football superstar back in his day, but that time has since faded. When a messy drunk driving incident lands him in jail, Paul finds he was specifically requested by Warden Hazen, played by James Cromwell, a duplicitous prison official well aware of Paul’s athletic skills. Paul has been assigned the task of assembling a team of convicts to square off in a football game against the sadistic guards. With the help of fellow convict Caretaker, played by Chris Rock, and an old legend named Nate Scarborough, played by Burt Reynolds to coach, Crewe is ready for what promises to be a very interesting game.
The Longest Yard is a remake of the 1974 film by the same name. The 1974 version also starred Reynolds and he provides that connective tissue for the most recent entry in the franchise. It was tough to choose which version of the movie should make the list, but I think a stacked cast of talented actors puts the new version over the edge. Watching Crewe, Caretaker and Scarborough put together a team that includes names like Nelly and Michael Irvin to play in a game called by Verne Lundquist is a blast and now is as good a time as any to seek out a football broadcast.
7. Kingpin (1996)
Roy Munson, played by Woody Harrelson, was the state bowling champion in 1979. Unfortunately, soon after he earned that honor, his hand was removed after trying to cheat the wrong guys. For the last 17 years he has been living a very unhappy life selling bowling equipment, with a rubber hand. And now he meets Ishmael, a young Amish man played by Randy Quaid who is a natural born bowler. After convincing Ishmael to come with him and use his talents to win money on the professional bowling circuit to help save his family’s farm, the two head out and start winning tournaments.
If it wasn’t for The Big Lebowksi, this may be the only film you think of when you think of bowling. Kingpin features a classic story of redemption as Roy tries to make up for past failures and overcome his lifelong rival, Ernie McCracken played by Bill Murray.
6. The Waterboy (1998)
Bobby Boucher, played by Adam Sandler, is 31, lives at home with his mother, played by Kathy Bates, and is the waterboy for the University of Louisiana Cougars. One day he is fired and ends up being the waterboy for a down-and-out college team, the South-Central Louisiana State University Mud Dogs. During an incident at practice, Bobby demonstrates himself to be a ferocious tackler, and he is brought on to the team to play linebacker. Thanks to him, the Mud Dogs’ fortunes soar but his mother doesn’t approve of him playing football or of the girl Bobby keeps growing closer to.
Sandler is the main star the film and the Mud Dogs but Kathy Bates’ performance as Mama Boucher is what puts The Waterboy this high on the list. Her relationship with Bobby gives a very silly, lighthearted film some added weight and culminates in a powerful scene just before Bobby leads one of the most historic comebacks in college football history.
5. Talladega Nights: The Ballad of Ricky Bobby (2006)
NASCAR stock car racing sensation Ricky Bobby, played by Will Ferrell, is a national hero because of his “win at all costs” approach. He and his loyal racing partner, childhood friend Cal Naughton Jr., played by John C. Reilly, are a fearless duo knows as Shake and Bake by their fans for their ability to finish so many races in the no. 1 and no. 2 positions. When flamboyant French Formula One driver Jean Girard, played by Sacha Baron Cohen, challenges Shake and Bake for the supremacy of NASCAR, Ricky Bobby must face his own demons and fight Girard for the right to be known as racing’s top driver.
I think growing up in the south makes this movie noticeably better. Growing up in a world that is in love with NASCAR gives you the necessary context to love Talladega Nights. Ferrell and Reilly have near perfect on-screen chemistry and continued to work together after their time as Shake and Bake. As with most great sports comedies, the supporting characters truly stand out. Ricky’s parents, Jane Lynch and Gary Cole are phenomenal, and Cohen has a perfect balance of silliness and dry humor as Girard. Just remember, If you ain’t first, you’re last.
4. Slap Shot (1977)
In the fictional small town of Charlestown, the local mill is about to lay off 10,000 workers, indirectly threatening the existence of the town’s minor league hockey team, the Charlestown Chiefs. After discovering that the team is to be folded, player-coach Reggie Dunlop, played by Paul Newman, lets the Hanson Brothers, the club’s recent acquisitions, loose on their opponents. The brothers’ actively violent and thuggish style of play excites the fans. Dunlop retools the team, using violence to draw big crowds. The team’s new style produces unintended consequences that affect not only Dunlop, but the Chiefs’ star player, Ned Braden, played by Michael Ontkean, along with the rest of the team.
Slap Shot is the go-to answer for a lot of people when you ask about their favorite hockey movies. There isn’t as much depth in the hockey genre as there is in some other sports but that doesn’t mean this film hasn’t earned its spot on the list. Director George Roy Hill does a great job of controlling the pace and energy of the film that is help together by a stellar comedic performance from Paul Newman.
3. Dodgeball: A True Underdog Story (2004)
Peter LaFleur, played by Vince Vaughn, is a charismatic underachiever and proprietor of a rundown gym called Average Joe’s. The facility’s clientele of less-than-average Joes includes: a self-styled pirate played by Alan Tudyk, a scrawny nerd who dreams of impressing an unattainable cheerleader played by Justin Long, an obsessive expert of obscure sports knowledge played by Stephen Root, a dim-witted young man and a cocky know-it-all who, of course, really knows nothing. Peter’s humble gym catches the eye of White Goodman, the ego-maniacal owner of Globo Gym played by Ben Stiller, a gleaming monolith of fitness. White intends to take over Average Joe’s, and Peter’s non-existent bookkeeping is making it all too easy for him. A foreclosing bank has stationed attorney Kate Veatch, played by Christine Taylor, inside Average Joe’s to finalize Globo’s takeover but Peter’s boyish charms win her over and Kate joins his team of social rejects to beat the odds and try to save Average Joe’s. How? With dodgeball.
Ben Stiller’s performance as White Goodman makes Dodgeball a sports comedy classic. The entire film is cast perfectly but Stiller, who is also the director of the film, steals every scene he’s involved in. Rip Torn is outstanding as an older Patches O’Houlihan and Gary Cole and Jason Bateman will forever be the true “ESPN8 the Ocho” crew as Cotton McKnight and Pepper Brooks. All of the technical aspects of the film are well-made, and the story is well-written but it’s the individual characters and their quirks that make Dodgeball great.
2. Happy Gilmore (1996)
Happy Gilmore, played by Adam Sandler, has long aspired to be a hockey player. Despite a powerful slapshot, Happy’s volatile behavior excludes him from being accepted by any hockey team. Furthermore, Happy’s grandma is being evicted from her home after failing to pay her taxes. After playing with some golf clubs and learning he can hit golf balls far distances, he decides to join the PGA Tour in an effort to win money to buy back his grandma’s home. Happy’s bad-boy image attracts a loyal following, but also attracts the attention of Shooter McGavin, played by Christopher McDonald, the favorite to win the PGA Tour who is worried that Happy’s rise to stardom will undermine his shot to win.
Happy Gilmore is one of those movies that we always stop to watch in my house when we see it on TV. It’s an endlessly rewatchable film packed with fun characters including Carl Weathers as Chubbs, an infamous cameo appearance from Bob Barker and maybe the most underrated character in the film, Hal, the iron-fisted retirement home nurse played by Ben Stiller. Happy is one of my favorite Sandler characters but what brings this one home for me is McDonald’s unforgettable, villainous performance as Shooter McGavin. Let’s get one thing straight, this is Shooter’s tour.
1. Caddyshack (1980)
Danny Noonan, played by Michael O’Keefe, is a young caddy at Bushwood Country Club who has no idea about where his future will lead. His best chance at getting his life on track is to earn a caddy scholarship from Judge Elihu Smails, played by Ted Knight, the owner of the country club. Al Czervik, played by Rodney Dangerfield, is a rude, and overly eccentric millionaire who has interests in purchasing Bushwood. Judge Smails shows a quick disliking towards Al and soon there is a conflict between the Judge and Al, the Judge and Danny, and even between the Judge and Ty Webb, played by Chevy Chase, the charming golfer who is slowly helping Danny figure out his real goals. On the outside of this conflict is Carl Spackler, played by Bill Murray, the golf course’ grounds keeper, whose goal is to eliminate a rampaging gopher that is chewing up holes throughout the golf course.
There is never not a good time to watch Caddyshack. Everything fits together perfectly, the cast, the writing and the direction of the late, great Harold Ramis. Dangerfield, Chase, Knight and Murray carry most of the comedic load throughout the film but there are so many smaller supporting characters that stand out, like Lou Loomis and Dr. Beeper. The combination of the big stars providing laughs and memorable supporting characters moving around them makes Caddyshack arguably the greatest sports comedy of all time.
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