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Entertainment

‘Happy Gilmore 2’: The wildest celebrity cameos, from Travis Kelce to Ken Jennings

Last updated: July 26, 2025 3:59 pm
Oliver James
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‘Happy Gilmore 2’: The wildest celebrity cameos, from Travis Kelce to Ken Jennings
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Spoiler alert! We’re discussing major plot details from the sequel “Happy Gilmore 2” (streaming now on Netflix).

Contents
Bad BunnyBenny SafdieTravis KelcePlease Don’t DestroyEric André and Margaret QualleyEminem, Post Malone and Kid CudiGuy FieriHaley Joel OsmentSteve BuscemiKen JenningsSean Evans from ‘Hot Ones’Marcello Hernández

It’s all in the hips.

Adam Sandler’s oafish pro golfer is back on screen for the first time in nearly 30 years, in a new movie that follows the titular Happy Gilmore as he attempts to get back in the game and raise his five kids after the death of wife Virginia (Julie Bowen) in a hurtling golf ball accident. Christopher McDonald, as Happy’s nemesis Scooter McGavin, and Ben Stiller, as abusive orderly Hal L, have also returned.

Here are some of the most memorable A-list appearances from actors, musicians and athletes throughout the new movie:

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Bad Bunny

The Puerto Rican hitmaker continues to make inroads into acting, after 2022’s “Bullet Train” and Darren Aronofsky’s “Caught Stealing” (in theaters Aug. 29). Here, he plays Oscar, a good-natured busboy-turned-caddie for Happy.

Benny Safdie

After co-directing Sandler in 2019’s nail-biting “Uncut Gems,” Safdie chews the scenery as main antagonist Frank Manatee, the conniving owner of a sports drink company.

Travis Kelce

Benito Antonio Martínez Ocasio, left, and Travis Kelce in “Happy Gilmore 2.”

The Kansas City Chiefs tight end (and beau to Taylor Swift) makes an amusing cameo as a strict restaurant manager, whom Oscar dreams of covering in honey and feeding to a bear.

Please Don’t Destroy

The “Saturday Night Live” viral sketch trio appears throughout the movie: Martin Herlihy, who is also the son of the film’s co-writer, Tim Herlihy, plays an amateur golfer who mercilessly taunts Happy when he comes out of retirement. Ben Marshall and John Higgins also make blink-and-you’ll-miss-it cameos as irreverent, shirtless spectators during a game.

Eric André and Margaret Qualley

Margaret Qualley, left, Martin Herlihy and Eric André in “Happy Gilmore 2.”

Like Herlihy, the stand-up comedian and “The Substance” actress pop in as unimpressed putters who fall victim to a fiery golf cart crash at the hands of the inebriated Happy.

Eminem, Post Malone and Kid Cudi

The rappers all have small but memorable roles in the new film: Eminem, as a bearded heckler named Donald Jr.; Malone, as outlandish golf commentator DJ Omar Gosh; and Cudi, as an FBI agent who apprehends Stiller’s character at the end of the movie.

Guy Fieri

The “Diners, Drive-ins, and Dives” favorite drops in late in the movie as a golf tournament official who gets the crowd fired up.

Haley Joel Osment

Joseph Vecsey, left, and Haley Joel Osment in “Happy Gilmore 2.”

The Oscar-nominated child star, best known for “The Sixth Sense” and “A.I. Artificial Intelligence,” has a substantial supporting role as Happy’s cocky golf rival Billy Jenkins.

Steve Buscemi

The Hollywood veteran has appeared in many of Sandler’s movies, including “The Wedding Singer” and “Billy Madison,” and has a minor part here as Happy’s eccentric neighbor.

Ken Jennings

The “Jeopardy!” host plays himself at the start of the film, as a long-retired Happy is distressed to learn that none of the game show’s contestants have any idea who he is.

Sean Evans from ‘Hot Ones’

Sean Evans in “Happy Gilmore 2.”

Frank Manatee goes on a promotional tour in support of his sports drink brand, which includes an interview with celebrity wings master Evans, as well as real-life podcasters Bobby Lee and Alix Earle.

Marcello Hernández

Marcello Hernández, left, Adam Sandler and Benito Antonio Martinez Ocasio in “Happy Gilmore 2.”

The “Saturday Night Live” heartthrob, who’s beloved for his viral “Domingo” sketches, is in and out as Oscar’s cousin, Esteban.

This article originally appeared on USA TODAY: ‘Happy Gilmore 2’ cast: Travis Kelce, Eminem, more A-list cameos

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