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Adam Sandler's sports comedy expertise returns with Happy Gilmore 2, nearly three decades after the original. In the aftermath of the first film, Happy (Sandler) has won several major golf championships. But since accidentally killing his wife while playing, he has quit the sport. However, a comeback is imminent, as Happy must find a way to fund his youngest daughter's ballet education.
Happy Gilmore 2, which was released directly on Netflix, received positive reviews for Sandler's quintessential comedic bits. His interactions with all kinds of celebrities who make surprising cameos are hilarious and unexpected. From sports personalities like Bubba Watson to entertainers like Eminem, there is no dearth of appearances.
Disclaimer: The list is in no particular order, and all opinions in this article belong to the writer. Spoilers for Happy Gilmore 2 ahead.
Eminem, Bubba Watson, and other best cameos in Happy Gilmore 2
1) Eminem
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While the Grammy award-winning singer-songwriter has a short cameo in Happy Gilmore 2, it was one of the more iconic ones. He plays the son of Donald, played by Joe Flaherty, the bitter heckler in the original movie whose comedic catchphrase involved yelling "Jack*ss!" every time Happy took a swing. Flaherty passed away in 2024, but the movie found a way to pay tribute to his character.
Eminem plays into the manic chaos of his character's father. He gives Happy an attitude and heckles him, knowing Happy will end up in jail for fighting him. However, Happy's sons show up and throw the heckler into a pond, where his hilarious empty threats are met with loud chomping from the alligators.
2) John Daly
Happy Gilmore 2 is a comedy about a golfer on a mission, so it makes perfect sense for Happy's life to coincide with some iconic golfers who have played the game. One of the many cameos includes John Daly, the two-time Major champion nicknamed the "Wild Thing" for his attitude on and off the course.
While he is known for his unbelievable driving distance from the tee, his role in the movie involves spending his retirement days lounging in the Gilmore family's garage. He plays himself and is Happy's friend and mentor, who goes to him for advice after hitting rock bottom in his personal life.
3) Guy Fieri
The American restaurateur and Emmy Award-winning culinary show host, with programs like Guy's Grocery Games, makes a quick but memorable cameo in Happy Gilmore 2. His signature frosted tips and sunglasses make it easy for fans to recognize him in the climax sequence.
Fieri plays the championship tournament starter and signals that the game is underway. As one of the many real-life personalities who played a small role in the film, he gets the crowd hyped up and ready for the clash.
4) Travis Kelce
The popular tight end for the Kansas City Chiefs plays a comically evil role in Happy Gilmore 2 as a waiter at the club restaurant the night before the Tour Championship. He shares screen space with Bad Bunny's Oscar and was praised by Sandler for his acting chops.
Kelce's character puts on a nice guy persona for the rich and famous patrons at the restaurant, but his true self comes out when he fires Oscar over a tiny error. This makes Oscar envision Kelce's character getting devoured by a bear in a later scene. The star's cameo adds humor to the already funny premise.
5) Post Malone
In a blink-and-you-will-miss-it moment, the popular singer and rapper Post Malone appears as DJ Omar Gosh. As the Maxi Tour Challenge is underway, many star golfers and celebrities show up one after the other. Gosh ends up on the commentary team with Verne Lundquist and Jack Beard.
He is heavily dressed and accessorized in Happy Gilmore 2, but the Grammy artist is instantly recognizable in the role. He throws in hilarious quips and personal commentary about the game. Next to the more well-known commentators, his actions appear more exaggerated and add to the film's comedic premise.
6) Scottie Scheffler
Another golfer who has a bigger cameo in Happy Gilmore 2 is Scottie Scheffler. He plays himself and is one of the first ones to tee off in the Maxi Tour Challenge, but his game is cut short after a physical altercation with actor Oliver Hudson (who also has a cameo) leads to his arrest.
Art imitates life for Scheffler's character, and makes light of an infamous time in 2024. Scheffler was arrested and charged with felony assault of a police officer and for breaking other traffic rules. So when he says, "Not again!" as he is handcuffed, fans can't help but laugh out loud.
7) Stephen A. Smith
Every sports fan knows analyst Stephen A. Smith. His booming voice and big personality are instantly recognizable in Happy Gilmore 2, as he breaks down Happy's consecutive days of success in the Tour Championship, and eventual failure after the first three games.
He plays himself, so the exaggerated commentary increases the stakes and amps up the movie's humor. Other sports commentators and presenters who appear are Chris Berman, Jim Gray, and Dan Patrick. Their appearance adds a realistic touch to Happy's sporting journey.
8) Nelly Korda
Shooter McGavin (Christopher McDonald), the antagonist in the first edition, returns to call a begrudging truce with Happy in Happy Gilmore 2. He works with Happy to take Maxi Golf down. But since his loss to Happy in 1996, the character is revealed to have been in psychiatric care at the Westford State Mental Hospital.
On the parole board deciding if Shooter's mental health is okay for release are three people: Dr. Hertz, Dr. Young, and Dr. Silver. Dr. Young is none other than Nelly Korda, the current #1 ranked golfer on the LPGA tour. The movie gives her a different role from her off-screen career, making it a quick and fun cameo.
9) The Sandlers
Adam Sandler's running gag is adding his family members in cameo roles. Fans previously saw them in movies like Just Go With It, Grown Ups, and Jack and Jill. So they have become some of the best Happy Gilmore 2 cameos. Sandler's wife, Jackie, has a brief cameo as his daughter Vienna's ballet teacher, Monica. She submits Vienna's dance tape to a Parisian ballet school and gets her a spot there.
His daughter, Sunny Sandler, plays his daughter in the movie too. Her dream of ballet school is why Happy goes back to golf in the first place. His other daughter, Sadie Sandler, plays Charlotte, who is Happy's friend at the Healing Alkies for Life program, and helps him quit alcohol.
10) Ben Stiller
While Ben Stiller's role has a lot more scenes than what a cameo entails, his role in the larger scheme of Happy Gilmore 2 becomes one because of how many familiar faces appear. He reprises his role as Hal L. but returns as the power-hungry and abusive head of Healing Alkies for Life (HAL).
In the original, Stiller was an evil manager of a retirement home where Happy's grandmother lived, where he forced the elderly to perform manual labor to his benefit. Looks like his character went from one evil job to the next.
Happy Gilmore 2 is streaming exclusively on Netflix.
