The long-awaited sequel is jam-packed with celebrity walk-ons—some hilarious, some awkward, and a few that had fans pausing to make sure they really saw who they thought they saw.
From global music icons to nostalgic Hollywood throwbacks, these cameos dominated the conversation around Happy Gilmore 2.
Bad Bunny steals the spotlight
Bad Bunny’s cameo isn’t just a blink-and-you ’ll-miss-it moment—he’s practically part of the story. Playing Oscar, Happy’s eccentric new caddy, the global reggaeton superstar adds actual personality and screen time to the film.
He’s one of the few celebrity appearances that feels like a real character instead of a random name-drop, and his chaotic dynamic with Adam Sandler is surprisingly fun to watch. For fans who didn’t expect him to lean into golf comedy, this cameo was a pleasant surprise.
Eminem pops up, vanishes
Slim Shady’s cameo is short but instantly recognizable. Eminem appears as Donald Jr., the son of the notorious heckler from the original movie, giving a nod to one of the franchise’s funniest side characters. His scene may last only a few seconds, but that was enough for the internet to light up with memes and screenshots. It’s one of those cameos you can’t help but rewind just to make sure you didn’t imagine it.
Post Malone gets loud
Post Malone doesn’t just show up—he brings his signature chaos with him. Playing DJ Omar Gosh, the Maxi League’s commentator, the chart-topping artist dials everything up to 11. His wild energy and over-the-top delivery match the absurdity of Happy Gilmore 2 perfectly. Whether you love Posty or not, you can’t deny he makes the tournament scenes a lot louder, and maybe even a little more entertaining.
Travis Kelce vs. the bear
NFL star (and Taylor Swift’s boyfriend) Travis Kelce gets what is easily the movie’s most viral cameo. In a ridiculous gag, he’s tied to a pole, covered in honey, and mauled by a bear—a setup tailor-made for social media.
Kelce’s comedic timing isn’t exactly refined, but the sheer absurdity of the scene makes it impossible to forget. It’s a classic Sandler-style bit: over the top, unnecessary, and guaranteed to get a reaction.
Steve Buscemi is weird and wonderful
Veteran actor and Sandler favorite Steve Buscemi shows up as Happy’s unhinged neighbor, and his deadpan delivery is flawless as always. Even though his screen time is brief, Buscemi brings an offbeat energy that perfectly fits the movie’s tone.
It’s the kind of cameo that feels effortless, proving once again that Buscemi doesn’t need much to steal a scene.
Guy Fieri goes full Flavortown
The “Mayor of Flavortown” himself, Guy Fieri, crashes the movie as a flashy Maxi Golf host. With his spiky hair, sunglasses, and over-the-top personality, Fieri basically plays himself—turning the tournament into a full-on food network spectacle. It’s pure Guy Fieri, which makes it both absurd and oddly fitting.
Fans of his TV persona will enjoy seeing him turn golf into Flavortown for a few minutes.
Ken Jennings, trivia king
Trivia nerds got a treat when Jeopardy! legend Ken Jennings appeared as himself. It’s a self-referential bit that feels tailor-made for Jennings’ personality, and it adds a fun layer for viewers who grew up watching him dominate on TV.
While his cameo won’t have casual fans rolling on the floor laughing, it’s the kind of Easter egg that makes you smile if you catch it.
Haley Joel Osment makes a comeback
The former child star of The Sixth Sense makes a nostalgic return as rival golfer Billy Jenkins. Seeing Haley Joel Osment pop up in a Sandler movie was a surprise for many fans, and his presence adds a touch of early-2000s Hollywood nostalgia.
He throws himself fully into the role, making his character feel more than just a quick wink to the audience.
John Daly in his natural habitat
Golf rebel John Daly doesn’t need to act much in this movie, which is exactly why his cameo works. Living in Happy’s garage as his beer-guzzling buddy and mentor, Daly feels like he was born to play this role. He brings authentic golf-world credibility, but also the kind of unpolished charm that fits perfectly in a Happy Gilmore sequel.
Rory McIlroy brings the star power
One of the world’s most recognizable golfers appears as himself in the movie’s climactic tournament scenes. Rory McIlroy’s presence gives the tournament a dose of real-life star power, and golf fans were thrilled to see him on screen.
It’s not a joke-heavy cameo, but it lends credibility to the film’s golf universe—something the first movie built its legacy on.
Who did we miss? Who’s your fave?
There were so many cameos in Happy Gilmore 2, it was hard to keep track. Which ones made you laugh, cringe, or hit rewind? Did we forget your favorite? Whether you loved the big names or the deep-cut callbacks, there’s no denying this movie is a full-blown cameo circus—and that’s exactly why everyone’s talking about it.
