Happy Gilmore 2: Every (Exhaustive) Cameo, From Least to Most Surprising
In terms of awe-inspiring star power, it seems unlikely that any movie will ever beat the 60+ Hollywood cameos that Robert Altman managed to squeeze into his 1992 classic The Player, but Happy Gilmore 2 certainly has the numbers for a podium finish.
Before I start getting into all that and mixing up my sports metaphors, I should say that the film, aside from being a comedy, is much more of a golf movie than its predecessor. It’s also, in some ways, a movie about Sandler’s life and career. In my recommendation for JustWatch, I described it as a “heartfelt victory lap”—another non-golf sports metaphor, but a fitting one just the same.
Ranked from least to most surprising, let’s race through Happy Gilmore 2’s bulging Rolodex (which is a thing people still used when the original movie came out) of stars, assess what they add to the movie, and which other films and TV shows you'll know them from.
All The Men’s Golfers
If you’re a fan of podcasts, I’d recommend listening to the Happy Gilmore Rewatchables episode before diving into the new one. Not only is Benny Safdie one of the hosts (there to promote the Sandler-starring Uncut Gems, long before being cast as the villain in Happy Gilmore 2), but there is also a small list of critiques, which are all pretty much addressed in the sequel. One of these is that the first movie needed—with all due respect to Mark Lye and Lee Travino—more golfers.
Happy Gilmore 2 more than makes up for it with a whopping 22 real players appearing in the sequel—in a way that kind of validates Gilmore’s place (and the original movie’s place) in the golf world. Leading the men’s side of the golfing cameo draw are the four greats who Happy joins in the Maxi tournament: Rory McIlroy (charming if a little wooden), Scottie Scheffler (kinda hilarious), Brooks Koepka (and his wife Jena Sins), and Bryson DeChambeau.
Next up is a role for Will Zalatoris, who simultaneously plays himself and a grown-up version of Happy’s original caddy from Part One—one of many links to the previous movie. John Daly also gets a big role as a man who, for some unexplained reason, lives in Happy’s garage. Justin Thomas also comes off well as the first pro Happy plays against.
In addition, there’s a clubhouse scene featuring the legends Fred Couples (who does a good comedic bit involving dessert), Nick Faldo, 85-year-old Jack Nicklaus, Corey Pavin, and a returning Travino alongside current stars Jordan Spieth, Xander Schauffele (who keeps making “that’s what she said” jokes), Rickie Fowler, Keegan Bradley, and Collin Morikawa. Bubba Watson pops up for a few seconds, and Hunter Mahan also appears, but only as Sandler’s stunt/golf double.
All The Women’s Golfers
On the women's side of the golfing cameos draw, Nelly Korda (the current LPGA #1) and Nancy Lopez appear on the parole board of the mental hospital where Shooter McGavin is being held, and, later on, can be seen watching the Maxi tournament on TV. Paige Spiranic, a golf influencer, also appears as an employee in a sports shop where Happy goes to buy new gear, offering another little moment of comic relief.
Perhaps the funniest of them all is British player Charley Hull, who pops up for a few seconds as the owner of the miniature golf course where Chubb Peterson’s son, Slim (played by Sandler regular Lavell Crawford in yet another cameo), is working—until she calls him a “big pork chop” and fires him.
All The Other Sports Stars, From American Football to the WWE
Filling out the other sports roles in Happy Gilmore 2—and adding to the movie’s sense of chaos—are the retired American Football star Reggie Bush and professional wrestlers Rebecca Quin, aka Becky Lynch (who gets to twist her fellow countryman Rory McIlroy’s nipples), and Nikki Garcia, aka Bella— who all appear on the the opposing side in the Maxi tournament. Another WWE star, Maxwell Jacob Friedman, has fun playing the bulkiest of Sandler’s four sons.
Elsewhere, Taylor Swift’s boyfriend and Kansas City Chief Travis Kelce shows he has some acting chops, playing a bossy shift manager at the country club (where his dad, Ed, can also be seen). WNBA star Kelsey Plum pops up as a course manager while 224cm Serbian basketball giant Boban Marjanović plays the son of Happy’s former boss, Mr Larson, who Richard “Jaws” Kiel memorably played in the first film—another callback that fans will appreciate.
Sportscasters Verne Lundquist, Jim Grey & Dan Patrick
Another one for fans of the original film is real-life former sportscaster Verne Lundquist, who delightfully returns (and delightfully is still alive at 85 years old) alongside Jack Giarraputo (more on him in a moment) in the commentary box. He even gets to don an eccentrically colourful shirt for the Maxi tournament. Dan Patrick, another real sportscaster who fans of Sandler movies will recognise, also pops up later on riding an exercise bike, as does another veteran, Jim Grey.
Tim Herlihy
Another returning cameo that Sandler fans will love is the movie’s co-writer, Tim Herlihy (and yes, that’s SNL comedian Martin’s dad), who has worked with Sandler on a wide range of movies going back to Happy Gilmore, Big Daddy, and Little Nicky. In Happy Gilmore 2, he plays the third member of the parole board at Shooter’s hospital.
Dennis Dugan & Jack Giarraputo
The two other longtime collaborators from Sandler’s Happy Madison production company who appear are director Dennis Dugan, who reprises his role from the first movie as the league’s commissioner, and producer Jack Giarraputo, also reprising his role as a sportscaster from Happy Gilmore—these two don’t add much to the plot, but it’s nice to see so many of Sandler’s behind-the-camera collaborators getting in on the action.
Rob Schneider
Incredibly, Happy Gilmore was one of Sandler’s only Happy Madison movies in which Rob Schneider didn’t appear, so if you’re a fan of Schneider’s many cameos, you’ll appreciate the corrective. Sandler makes up for it here by adding a Schneider appearance in the “Happy Place” to say his immortal four-word catchphrase (you know the one) in a wisely recast role.
Steve Buscemi
Another actor who has been popping up in Sandler movies since Airheads and Billy Madison—and who we really don’t see enough of these days—is the legend, Steve Buscemi. If you’re a fan of the actor, it’s a real nostalgic hit to see him pop up in a Sandler movie again.
In Happy Gilmore 2, playing Happy’s slightly unhinged neighbour, he gets to imitate Sunny’s dance moves, pee in a postbox, and fight John Daly on a couch. Give the man an Oscar already!
Blake Clark
Another Sandler regular, Blake Clark (whose long career of bit parts includes voicing Slinky the Dog in Toy Story 3 and 4), appears in a role not dissimilar to his Farmer Fran from The Waterboy. This is one that only the most dedicated Sandler followers will notice.
Jon Lovitz
Yet another Happy Madison regular that Sandler fans will be happy to see is the great Jon Lovitz. The actor appears as the snooty golfer at the driving range who foolishly attempts to mimic Happy’s signature swing.
Jonathan Loughran
And finally, the last of the Happy Madison crew to appear is Jonathan Loughran, who again, only Sandler megafans will probably notice. Loughran is best known for playing Lyle Robideaux, Sandler’s crosseyed teammate in The Waterboy. In Happy Gilmore 2, Loughran reprises his role as a character who is officially called the “Crazy Eyed Orderly” in Part One.
All The Sandlers
For all the arguably mid-tier comedies that Sandler has made with Netflix over the years, it’s endearing how often he’s found ways to get his family involved—it’s actually something I’ve always liked about his approach to work and stardom.
These include shooting films in locations that the whole family wanted to visit together and even casting his daughters, Sunny and Sadie Sandler, in the recent You Are So Not Invited to My Bat Mitzvah. Both appear again here: Sunny as Happy’s daughter, who is hoping to get into dance school in Paris (basically the catalyst for the whole movie), and Sadie as Cudi’s partner in the FBI. Sandler’s wife, Jackie, plays Sunny’s dance instructor while his mother, his brother-in-law, and mother-in-law, Judy, Cristopher, and Lila, all pop up in tiny roles. It’s a family affair!
Cameron Boyce
The most touching addition to the film's cameo brigade is the late Cameron Boyce, a child star who played Sandler’s son in Grown Ups and Grown Ups 2. The young actor, who passed away tragically in 2019, can be seen on the television screen in Wyatt and Plum’s golf shack.
All The Music Stars, From Bad Bunny to Eminem
One of the most significant of all the Happy Gilmore 2 cameos is Bad Bunny, who has more than enough screen time to warrant exclusion from this list, but it would be strange not to mention him all the same. As Oscar, he begins as Kelce’s unlucky employee in the country club but ends up as Happy’s loyal caddy—a callback to the vagrant Happy hires in the first movie.
Elsewhere, some cameos rarely last for more than a few seconds. Post Malone appears as the hilariously-named sports commentator DJ Omar Gosh. Kid Cudi plays an FBI agent. Singer-songwriter Andrew Wyatt appears opposite Plum at the golf course and, most deceptively of all, Eminem shows up under a fake beard and wig to play the son of Joe Flaherty’s character in part one—you know, the guy who tries to run Happy over and unsuccessfully invites Shooter to join him at the local Red Lobster.
Marcello Hernandez
The comedian and current SNL cast member Marcello Hernandez appears as the brother of Oscar (Bad Bunny). At first, he is mistakenly hired to be Oscar’s caddy and later offers to be a moving target for Sandler’s training session with his team. It’s one of the smaller cameos, but all of his bits land.
All The Podcasters, YouTube Stars & TV Hosts
Any movie looking to show that its characters’ actions are reverberating in the real world now looks to the stars of the smallest screen. The role once played by late-night legends like David Letterman and Conan O’Brein is now increasingly the realm of podcasters and YouTube stars, but Happy Gilmore 2 finds space for both the new and the old—and each of these helps to bring Happy’s story into the real world.
We get Sean Evans from Hot Ones, influencer Alix Earle, sports analyst Stephen A. Smith, ESPN host Chris Berman, Check Out That Stat host Treasure Wilson, Bad Friends hosts Bobby Lee and Andrew Santino, the rapper Cam’ron, and his Talk With Flee crew, and Jeopardy! host Ken Jennings.
Guy Fieri
The peroxide blonde patron saint of greasy food appears in an aptly cast cameo as the main announcer of the trashy Maxi tournament. He is unmistakable, even though this one is almost a blink and you miss it.
Eric André, Margaret Qualley & Martin Herlihy
Three of the most prominent cameos come from this unlikely trio of comedian, actress, and SNL star. André, Qualley and Herlihy are the first players Happy goes up against on his golf comeback, appearing on the course where Wyatt and Plum work and proceeding to get into all kinds of funny shenanigans together. These include Qualley dancing to 'Get Low' in a bunker and André crashing a golf cart in a moment that could easily have appeared in Jackass Forever. If you’re a fan of those movies, you’ll know what I mean.
