Adam Sandler is back on the big screen with the sequel to one of his most iconic films: Happy Gilmore. This new chapter not only brings back the chaotic charm of the original, but also features a massive lineup of celebrity cameos—from the worlds of music, sports, and film.
The most talked-about? Bad Bunny, who plays the caddie to Sandler’s character. The Puerto Rican superstar even joined the cast on Late Night with Seth Meyers to promote the film, adding even more buzz to the release.
However, el Conejo Malo is far from the only familiar face. The film includes over 70 cameos, adding a layer of fun and nostalgia to this cult comedy—just in time for its 30th anniversary.
Adam Sandler and rapper Bad Bunny during an interview with host Seth Meyers July 22, 2025 (Lloyd Bishop/NBC via Getty Images)
Premiering on Netflix on July 25, Happy Gilmore 2 also brings back beloved characters like Shooter McGavin (Christopher McDonald) and Virginia Gilmore (Julie Bowen), making it a must-watch for longtime fans and newcomers alike.
Happy Gilmore Cameos That Stole the Show (Spoiler Alert)
Eminem
One of the most buzzed-about cameos is from Eminem, who plays Donald Jr., the son of the infamous heckler who shouted “Jackass!” in the original film. In a direct nod to that scene, Donald Jr. yells the same insult during a tournament—only to get thrown into a gator-infested pond by Happy’s kids.
The Detroit rapper brings his signature sharp humor and chaotic energy, blending seamlessly with the film’s irreverent tone.
Bad Bunny and Travis Kelce
Meanwhile, Benito steals several scenes as Oscar Mejías, a golf club waiter who unexpectedly becomes Happy’s caddie. He may not know much about golf, but his charisma and flair make him an instant fan favorite. His on-screen rival? None other than NFL star Travis Kelce, and Taylor Swift‘s current boyfriend, who plays a hot-headed server constantly clashing with Oscar.
La escena de Travis Kelce y Bad Bunny en Happy Gilmore 2
But Bunny isn’t just part of the cast—he’s also involved behind the scenes. The reggaeton icon voices the lead character in the Latin American dub of Happy Gilmore 2, giving the film an extra layer of global appeal.
Post Malone
The singer makes a memorable appearance as DJ Omar Gosh, a fur-covered, over-the-top tournament commentator who brings pure chaos and flair to the play-by-play. He shares the broadcast booth with legendary sports commentators Verne Lundquist and Jack Giarraputo, creating a surreal blend of music, sports, and comedy.
🤠 Post Malone sur le tournage du film Happy Gilmore 2
— Post Malone 🛞 France (@Post_MaloneFR) July 28, 2025
Kid Cudi
Cudi shows up as an FBI agent who arrests Ben Stiller’s character, Hal. After the premiere, Cudi called the role “one of the top 5 moments” of his career in a social media post.
Framing this photo of Kid Cudi and Adam Sandler at the Happy Gilmore 2 premiere.
Rapper Cam’ron also makes an appearance, following Happy’s return to golf alongside his Talk with Flee podcast crew. Music producer Andrew Watt has a quick cameo too, playing one of the starters at the local golf course where Happy tries to get back into shape.
Just watched Happy Gilmore 2. Wasn’t expecting much but it made me chuckle and it made me tear up a bit (I blame the whisky).
An impressive list of Himself in the credits too 🤣 pic.twitter.com/vEIKeANz5t
But it’s not just musicians—Happy Gilmore 2 is packed with surprise appearances from across the entertainment world. You’ll spot golf legends like Rory McIlroy and Scottie Scheffler, TV personalities like Steve Buscemi and Guy Fieri, and even members of Adam Sandler’s real-life family: his wife Jackie, daughters Sunny and Sadie, and his mother Judith.
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