How many cameos can they pack into Happy Gilmore 2?

The answer is... the limit does not exist.

Set nearly 30 years after the original 1996 comedy, Happy Gilmore 2 brings back Adam Sandler’s title character who returns to golf to pay for his daughter’s ballet school tuition. Original cast members like Christopher McDonald (Shooter McGavin), Julie Bowen (Virginia Venit), Ben Stiller (Hal L.) reprised their roles, anchoring the film in its comedic roots.

Along with the original cast members, fans will recognize many more faces in Happy Gilmore 2. The movie is stacked with cameos from all areas of entertainment... sports, pop culture, music and more.

These guest appearances helped Sandler tap into the film's nostalgic appeal and energized longtime fans with surprise appearances. The cameos also helped position the sequel as a pop culture event, bridging generations through familiar faces. Many of the celebrities were quick to jump onboard thanks to Adam Sandler’s longstanding industry friendships and the playful, low-pressure atmosphere of a Sandler-led production.

Golf Legends Unite on Screen for Happy Gilmore 2

True to its golf‐centric story, the film features nearly two dozen professional golf legends showing up as themselves.

These include Jack Nicklaus, Rory McIlroy, Bryson DeChambeau, Jordan Spieth, Scottie Scheffler, Bubba Watson, and more. Basically everyone who's anyone in golf was a part of this production. In one scene, Lee Trevino even reprises his role from the original film with a trademark silent head‑shake at Happy’s antics — a cheeky callback to fans.

Music, Comedy, and Unexpected Inserts

The celebrity roll call continues across music and pop culture. Eminem plays the son of the heckler from the first movie and delivers the classic insult “jacka**” with a comedic twist. Post Malone appears as commentator “DJ Omar Gosh” alongside Verne Lundquist and Dan Patrick, delivering colorful commentary during tournament scenes. Kid Cudi (credited as Scott Mescudi) plays an FBI agent at the film’s end, rounding out the eclectic mix. Bad Bunny appears in a major supporting role as Happy’s new caddie, Oscar, bringing Latin trap charisma to the golf course.

Sports, Internet, and Friendly Faces

Beyond golf and music, the film includes a wide array of cameos from sports and digital media. NFL superstar and Taylor Swift's beau, Travis Kelce plays a memorable and somewhat antagonistic waiter. His brother, Jason Kelce's Instagram post sums it up well: “I’ve never loved and hated a waiter so much.”

Other athletic appearances include Reggie Bush, Nikki Garcia, Kelsey Plum, along with many more. Meanwhile, internet influencers and comedians—Alix Earle, Sean Evans, Jon Lovitz, Steve Buscemi, Rob Schneider, and longtime Sandler friends like Jonathan Loughran—round out the chaotic, inside‑joke‑infused ensemble.

Happy Gilmore 2 throws nearly fifty cameo appearances into the mix—blending golf legends, music icons, athletes, old friends, and internet personalities into one star‑packed comedy playground. It’s less about plot and more about celeb cameos and nostalgic callbacks, offering fans a wild scavenger hunt of familiar faces.