Every ‘Happy Gilmore 2’ Cameo, Ranked
Warning: Contains spoilers.
At this stage in his career, when Adam Sandler goes out to a prospective star of one of his projects, he probably doesn’t hear “no” a lot; it’s probably a lot likelier that he has to give a polite pass to the prospective stars who come to him. So it’s no surprise that Happy Gilmore 2 is loaded with celebrities, to the point where secondary and tertiary roles are filled by faces you know. Bad Bunny may be one of the biggest musical acts in the world right now; that doesn’t mean he can’t show up to play Happy’s new golf caddy. Oscar nominee Haley Joel Osment shows up as a new golf rival to Happy (having presumably been cast before his recent public disgrace). Margaret Qualley has worked multiple times with acclaimed director Yorgos Lanthimos; doesn’t mean she’d pass on a chance to play a snotty millennial golfer.
But what about the fame-os who appear in Happy Gilmore 2 less to play characters than to participate in a stunt? Let me count them down…
Don't Miss
First, though, I’ll note that this thing features what feels like 40 real pro golfers, probably half as many real sports commentators, several wrestlers and a basketball player. I’ll leave the ranking of everyone in that category to people who know who they are, which I do not. However, I’ll make two exceptions for outstanding achievement in this category.
John Daly: The unconventional golf star (to whom Happy bears more than a passing temperamental resemblance) is portrayed here as down on his luck; he’s living in Happy’s garage, but promises it’s only temporary since he’s made a down payment on a tent. Daly gives Happy actually good advice, and gets the pleasure of acting opposite Steve Buscemi as Bad Neighbor Pat. He also lets Happy trick him into drinking hand sanitizer Happy implies is actually liquor in a hand sanitizer bottle, then just develops a taste for it. He’s seated virtually the entire time he’s on screen.
Verne Lundquist and Jack Beard (Jack Giarraputo): Verne Lundquist was a real sportscaster; he’s still alive but he’s retired. Jack Giarraputo has produced multiple Happy Madison films, including this one, so this casting seems to be a favor/inside joke. I’m only giving them an honorable mention here because I love these Maxi Golf League broadcast jackets.
Now, onto the official ranking…
Bobby Lee
When sports drink creator Frank Manatee (Benny Safdie) goes on a podcast tour promoting his Maxi Golf League, his first stop is Bad Friends, on which Bobby Lee is a co-host with fellow comic Andrew Santino. Lee doesn’t get much to do except say “wow” about the promo Frank has just screened for them, but still, fuck that guy. By the way, it looks like they shot in Lee and Santino’s real podcast studio. I wonder if Lee ever stopped by the movie set any of the days when Sandler’s real daughters, Sunny and Sadie, were shooting.
Rob Schneider
In the original Happy Gilmore, Happy gets through his bouts of rage on the course by imagining himself in his happy place: His crush and eventual girlfriend Virginia (Julie Bowen) walks toward him in a teddy and garters, a huge pitcher of beer in each hand. Also, for unknown reasons, there’s a Little Person dressed as a cowboy offering support. Evidently, someone decided that visual gag wasn’t cool in 2025, because the cowboy in Happy’s new happy place is played by Schneider, doing his catchphrase from The Waterboy, “You can do eet!”
Kind of surprised Schneider would be party to such a “woke” casting decision, but whatever: glad he was able to make time in his busy schedule of getting booed offstage at hospital fundraisers.
Sean Evans
Naturally, Hot Ones — the most extreme talk show — is another stop on Frank’s promo tour for his extreme golf league. Evans is fine, but he’s just so ubiquitous. I feel like he’s so ready to cameo he probably sleeps in a lav mic.
Alix Earle
Another podcaster. Everything I know about this woman, as they say, has been against my will, but she does okay with her two lines, “That’s deep” and “Why is golf so boring and dumb?”
Actually, on the latter, I’m not 100 percent sure she doesn’t say, “What is golf so boring and dumb.”
Post Malone
Speaking of people who could stand to be a little less available: this guy. He plays DJ Omar Gosh, joining Lundquist and Beard at the Maxi Golf League broadcast desk. If he’s not in an actual Nudie suit, what we can see looks enough like them that I can’t be mad at his look.
Andrew Santino
Being the less offensive host in a scene with Bobby Lee isn’t a high bar, but Santino does clear it — until you remember that he regularly co-hosts a podcast with Bobby Lee and has for the past five years.
Ben Marshall
Like the original, Happy Gilmore 2 was co-written by Sandler and Tim Herlihy. If the latter name seems familiar to you, it may be because you know his son Martin as one-third of Please Don’t Destroy. Martin also appears in the film as Fitzy; with Qualley’s character Sally and Eric André’s Steiner, they make up a golf threesome to which Happy is added when he returns to a public course for what seems like the first time since Virginia’s death. The scene goes on long enough that Martin is basically playing a tertiary character in the movie, but his dad did find room for his buddies: Ben Marshall, the redheaded PDD guy, shows up in a brief sequence at Happy’s second tournament, joining four other dudes to spell “Happy’s” on their chests and “Wasted” on their backs. Look away to read a text, and you missed him.
John Higgins
Aaaaaand John Higgins, the third member of Please Don’t Destroy, is in the same scene, right next to Marshall. The only reason they aren’t tied is that Higgins did a better job drawing my eye; I had to rewind to confirm that Marshall was even in it.
Guy Fieri
I didn’t know what a “starter” is in golf. I looked it up. I think in the time it took me to copy and paste the link, I forgot. Regardless: the Food Network host plays the starter for a face-off between PGA golfers and the Maxi Golf League team, and wears a horned helmet to do so. I like to think it was his own.
Oliver Hudson
Oliver Hudson is also a podcaster — he co-hosts Sibling Revelry with his sister Kate, another star in the hyper-specific Netflix sports comedy category — but he’s not part of Frank’s promo montage; he plays Harley, one of the golfers in Frank’s stable who’s submitted to a surgical procedure to increase the range of motion in his hips. When he yells at his opponent, real golfer Scottie Scheffler, to miss his drive, Scheffler uses his newly acquired jerseying skills to take him out of commission instead. Harley remains unconscious for the rest of the movie, and Hudson fully commits to making him look nearly dead.
Travis Kelce
The man who may or may not be engaged to Taylor Swift shows that his above-par (pun slightly intended) Saturday Night Live performances weren’t a fluke. He acquits himself well as a country club waiter who’s mean to busboy Oscar (Benito Antonio Martinez Ocasio, aka Bad Bunny). After Oscar’s been hired on as Happy’s caddy, the Waiter reappears in Oscar’s happy place, as Oscar paints him with honey and leaves him tied to a post for a bear to have his way with — and if all that wasn’t already a Pornhub search term, it may be now.
Eminem
Since Joe Flaherty has died, Donald — the paid heckler from the original movie — couldn’t return. However, his disruptive spirit lives on in Donald Jr., played by Eminem. (Given the quality of his fake beard, disruptive spirit gum may also be involved.) Where could Eminem possibly summon the sense memory to play a loud jerk? We may never know.
Nick Swardson
The reason Frank has found a platoon of journeyman golfers willing to undergo his hip loosening surgery is that he has a proof of concept: Ben Daggett (Nick Swardson), the only golfer who could hit as far as Happy can. Ben had a severed ligament that was only discovered on an X-ray when some of the guys Ben hustled at a driving range shoved a golf shoe up his ass. A cautionary tale, to be sure, but Swardson makes the very most of his silent period scenes.
Jon Lovitz
As Happy is psyching himself up to go back on the PGA Tour, one of his training stops is a driving range, where he tests his precision by using his own drives to skeet shoot the balls of the “Dapper Man” next to him, played by Jon Lovitz. After Season 2 of Tires, this is the second Lovitz performance I’ve seen this year where he makes the most of limited screen time playing a guy appalled by a stranger’s boorish behavior. Is there a way for him to become a cameo artist full-time?
