In honor of the soon to be released Uncle Drew, I thought it only right to create a Top 5 for sports comedies.

Semi-Pro

Flint may be known for many things but the best thing to ever come from Flint is the Tropics. In this 2008 film, Will Ferrell, Woody Harrelson, and André Benjamin are on a struggling ABA team in the league’s final year. Adding in the history of basketball with the ABA-NBA merger cements the legitimacy of this film by covering an aspect seldom portrayed. Of course, when you have Will Ferrell, Jackie Moon, as the lead you can expect hijinks to ensue which this comedy has in spades. The notable moment of this film is when Ferrell fights a live bear in a caged octagon—talk about the greatest halftime show ever!

Despite this film being a comedy, Harrelson brings a dose of drama playing a washed-up alcoholic whose best years of basketball are behind him. The added tension of the merger adds to the excitement as the team needs to climb out of the cellar to even think of dreaming about playing in the NBA. The humor when it stems from basketball is also one of Semi-Pro’s strengths which can be seen when Moon creates, one of the greatest basketball moves, the alley-oop. If Uncle Drew can hold up as well as this fellow basketball comedy the movie has done something right.

Dodgeball: A True Underdog Story

Though dodgeball is rarely thought of when someone says sports, Dodgeball: A True Underdog Story is an instant thought that comes to mind when speaking of the sports/comedy genre. In this 2004 film, Vince Vaughn’s everyman character Peter LaFleur faces off against Ben Stiller’s arrogant tycoon White Goodman. The directorial debut of Rawson Marshall Thurber has smart writing displaying comedy utilizing satire, irony, and slapstick humor. The plot of a small company gym, Average Joe’s, fighting off the vulture-like qualities of the publicly owned Globo Gym is an interesting underdog story. Add in a solid supporting cast that really fills out the team and highlights the everyman motif and you have yourself a solid dodgeball team.

This film has notable celebrity cameos with Lance Armstrong, David Hasselhoff, Chuck Norris all playing crucial roles in the film. Any movie that has both Chuck Norris and The Hoff has to be on any “best of” list. The overall zaniness promotes the humorous aspect of this film lead by two comedy greats. Despite being more than a decade old this film holds up great and may have even gotten better with age. What once was panned by critics has gone on to become a beloved cult classic that may even produce a sequel.

The Waterboy

Adam Sandler movies have recently become nearly unwatchable but at the turn of the century he was putting out hit after hit. Two of these were great sports film with The Waterboy only making this list instead of Happy Gilmore because it is overshadowed by Caddyshack (and Sandler, unfortunately, wearing a Bruins jersey — I’m showing my Whalers bias here). In this football romp, a Cajun in the Louisiana bayou discovers his football prowess as he learns there is more to life than the swamp. This film is essentially a rag to riches story with loads of Cajun spice mixed with a fish out of water story.

The humor is the classic Adam Sandler routine of a simpleton fighting through adversity with slapstick driven comedy before his shtick got old. Sandler bull rushing while screaming is hilarious no matter how many times it’s done or who is tackled with my favorite being Colonel Sanders-like professor. Henry Winkler proves to be a good mentor for Sandler’s character, Bobby Boucher, as well as bringing his own comedic skills to the film. Overall, this film sums up why Adam Sandler took America by storm putting out great hits back in the late 90s with The Waterboy being one of his best films.

Major League

Baseball is said to be America’s pastime so the best comedy featuring the sport had to make this list. Major League features the Cleveland Indians where the new owner strips the team of its roster in order to move the team to Miami. The humor in this film may not be for everyone as it is driven entirely by baseball, but fans of the sport know how great this movie is. This film plays a lot on self-depreciation, which is heavily featured in Midwestern fanbases, with there even being a “free admission to anyone who was actually alive the last time the Indians won a pennant” promotion.

Featuring a stacked cast with a young Charlie Sheen and Wesley Snipes the cast is star driven and includes baseball personalities such as Bob Uecker Major League driving a line between fantasy and reality. This film is more grounded compared to the others on this list which gives it appeal as viewers can imagine it actually happening. Throw in Wild Thing as the soundtrack to this film and there are many aspects that make it an entertaining watch. While this new film holds up a proposed reboot of the series may have trouble holding up to its predecessor.

Caddyshack

The cast for this film is just ridiculous bringing together comedy greats like Chevy Chase, Rodney Dangerfield, Ted Knight, and Bill Murray. With this cast, you would anticipate that the humor in this film aces every joke which it does with expert comedic timing and slapstick. The banter between these greats delivered much of its humor as Caddyshack poked around the golf course. The interactions between a stuffed gopher puppet and Murray mirrored Looney Tunes with hijinks ensuing without managing to catch it. Dangerfield proves why he was one of the best comedians ever with jokes that stick well almost 40 years after the release. There are many plots in this which makes the film too unfocused at times but the core plot shines through delivering much delight.

The movie benefited from having a great soundtrack which heavily featured Kenny Loggins creating the theme song “I’m Alright” instantly becoming a classic. This lighthearted romp was great as it showed Country Clubs from the perspective of the working class which satirizes that way of living. You can forget about Caddyshack being the best sports comedy, this film has serious contention for best comedy period.

Whether Uncle Drew will live up to these films is still to be seen but if it’s better than Shaq’s Kazaam, it will be tolerable.

Let us know your thoughts. Do you think Uncle Drew will be a slam dunk?

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