Happy Gilmore 2 is a sports comedy film directed by Kyle Newacheck from a screenplay co-written by Tim Herlihy and Adam Sandler. The 2025 legacy sequel film picks up the story of Happy Gilmore as he has given up golf after a tragedy and taken up excessive drinking instead. Due to his alcoholism, Happy loses everything from his fortune to his house, and when his daughter wants to go to an elite ballet school, he must return to the golf course to earn the money. Happy Gilmore 2 stars Adam Sandler, Julie Bowen, Christopher McDonald, Benny Safdie, Bad Bunny, Ben Stiller, and Margaret Qualley. So, if you loved the bonkers story, hilarious comedy, and entertaining characters in Happy Gilmore 2, here are some similar movies you should check out next.
Happy Gilmore (Starz)
Happy Gilmore is a sports comedy film directed by Dennis Dugan from a screenplay co-written by Tim Herlihy and Adam Sandler. The 1996 film follows Happy Gilmore, an aspiring hockey player with extremely bad skating skills, who discovers that he is talented in the game of golf, and he must enter a golf competition to save his grandmother’s home. Happy Gilmore stars Adam Sandler, Christopher McDonald, Julie Bowen, and Carl Weathers.
The Waterboy (Rent on Prime Video)
The Waterboy is a sports comedy film directed by Frank Coraci from a screenplay co-written by Tim Herlihy and Adam Sandler. The 1998 film follows Robert “Bobby” Boucher, a socially inept young man with great tackling skills, as he is discovered by an eccentric football coach, but the only problem is that his mother doesn’t approve of his new hobby. The Waterboy stars Adam Sandler, Kathy Bates, Fairuza Balk, Jerry Reed, and Henry Winkler.
The Longest Yard (Hulu, Pluto TV, & Rent on Prime Video)
The Longest Yard is a sports comedy film directed by Peter Segal from a screenplay by Sheldon Turner. Based on the 1974 film of the same name by Tracy Keenan Wynn and Albert S. Ruddy, the 2005 film follows Paul “Wrecking” Crewe, a washed-up former NFL quarterback who is thrown into prison after causing mayhem while drunk and driving. He is soon forced to put together a football team comprising prisoners, which will go up against the prison guards. The Longest Yard stars Adam Sandler, Chris Rock, James Cromwell, Nelly, William Fichtner, and Burt Reynolds.
Dodgeball: A True Underdog Story (Hulu & Rent on Prime Video)
Dodgeball: A True Underdog Story is a sports comedy film written and directed by Rawson Marshall Thurber. The 2004 film revolves around a group of eccentric misfits who join hands to enter a Las Vegas dodgeball tournament to use the prize money to save their gym. Dodgeball: A True Underdog Story stars Vince Vaughn, Ben Stiller, Christine Taylor, and Rip Torn.
Billy Madison (Starz & Rent on Prime Video)
Billy Madison is a comedy film directed by Tamra Davis from a screenplay co-written by Tim Herlihy and Adam Sandler. The 1995 film follows Billy, an immature young man who must repeat school in order to get his hands on his father’s massive inheritance. Billy Madison stars Adam Sandler, Bradley Whitford, Josh Mostel, Bridgette Wilson, Norm Macdonald, and Darren McGavin.
Talladega Nights: The Ballad of Ricky Bobby (Rent on Prime Video)
Talladega Nights: The Ballad of Ricky Bobby is a sports comedy film directed by Adam McKay, who also co-wrote the screenplay with Will Ferrell. The 2006 film follows Ricky Bobby, a successful but immature NASCAR driver, but his good times come to an end when a French F1 driver beats him. Now he must train hard to win his place back. Talladega Nights: The Ballad of Ricky Bobby stars Will Ferrell, John C. Reilly, Sacha Baron Cohen, Gary Cole, and Michael Clarke Duncan.
Caddyshack (Philo & Rent on Prime Video)
Caddyshack is a sports comedy film directed by Harold Ramis, who also co-wrote the screenplay with Brian Doyle-Murray and Douglas Kenney. The 1980 film follows Danny Noonan, a young caddie at an exclusive golf course who must suffer the snobbery of rich golfers to earn money for college. Caddyshack stars Chevy Chase, Rodney Dangerfield, Ted Knight, Michael O’Keefe, and Bill Murray.
Blades of Glory (Netflix, Paramount+, & Rent on Prime Video)
Blades of Glory is a sports comedy film co-directed by Will Speck and Josh Gordon from a screenplay co-written by Jeff Cox, Craig Cox, John Altschuler, and Dave Krinsky. The 2007 film revolves around two Olympic ice skaters who go from being rivals to a duo after being debarred from men’s singles events. Blades of Glory stars Will Ferrell, Jon Heder, Will Arnett, Amy Poehler, William Fichtner, Jenna Fischer, and Craig T. Nelson.
The Benchwarmers (Rent on Prime Video)
The Benchwarmers is a sports comedy film directed by Dennis Dugan from a screenplay co-written by Allen Covert and Nick Swardson. The 2006 film revolves around a trio of guys who never got respect, both in their childhood and adulthood. To rectify that, they decided to form a baseball team to play against standard children’s teams. The Benchwarmers stars Rob Schneider, David Spade, John Heder, Jon Lovitz, Craig Kilborn, Molly Sims, and Tim Meadows.
The Internship (Hulu & Rent on Prime Video)
The Internship is a comedy film directed by Shawn Levy from a screenplay co-written by Vince Vaughn and Jared Stern. The 2013 film follows Billy McMahon and Nick Campbell, two middle-aged salesmen who are laid off from their jobs and decide to start fresh by getting an internship at Google. The Internship stars Vince Vaughn, Owen Wilson, Rose Byrne, Max Minghella, Dylan O’Brien, and Aasif Mandvi.