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‘Happy Gilmore 2’ ultimate cameo guide — from Haley Joel Osment to Post Malone
“Happy Gilmore 2” landed on Netflix on Friday, July 25, almost 30 years after Adam Sandler’s failed hockey player turned unorthodox golf sensation stunned the world by trouncing top pro Shooter McGavin (Christopher McDonald) and winning back his beloved grandma’s house. Less than 24 hours after its release, the long-awaited sequel is already breaking the internet.
Netflix’s latest original is packed with familiar faces and cameos that have everyone talking. Sandler reprises his role as the hot-headed golfer, and he’s joined by an even more star-studded cast than the original, including Christopher McDonald as Happy’s nemesis Shooter McGavin, Ben Stiller as Hal L, and Julie Bowen as Virginia Gilmore.
All the sequel’s hype has even landed the original 1996 film in the Netflix top 10 list as viewers eagerly revisit one of the most enduring ’90s comedy classics. Just be sure to watch the first “Happy Gilmore” sooner rather than later; you only have until August 1 to fit in a double feature, as it’s one of 48 movies leaving Netflix next week.
As in the first film, “Happy Gilmore 2” includes several jaw-dropping cameos that you’ll have to see to believe. The sequel introduces a ton of new characters, including Sandler’s daughter Sunny as Happy’s daughter Vienna, Bad Bunny as Sandler’s caddy Oscar, and dozens of real-world golfers, musicians, and celebrities that Sandler somehow roped into appearing in the film.
Every cameo in ‘Happy Gilmore 2’
With so many celebrity cameos popping up left and right, it’s practically impossible not to miss one or two. Just be warned: We’re discussing major plot details from “Happy Gilmore 2,” so there’s plenty of spoilers ahead!
From Haley Joel Osment as a surgically-enhanced golf pro to Travis Kelce as a golf fanboy waiting tables, here’s who to look out for in “Happy Gilmore 2” this weekend.
Bad Bunny as Oscar Mejías
With Happy coming out of retirement and back on the green, he needs a new caddy to be his right-hand man. The Puerto Rican hitmaker Bad Bunny plays Oscar, a good-natured busboy who takes on the job. It’s the popstar’s latest movie cameo after we saw him in 2022’s “Bullet Train” and 2021’s “F9: The Fast Saga.”
Steve Buscemi as the neighbor
Long-time Sandler collaborator Steve Buscemi makes an early cameo in “Happy Gilmore 2.” After Happy loses his grandma’s house for a second time following Virginia’s death, he and his daughter are forced to move to a seedier side of town. Buscemi plays their new oddball neighbor.
Post Malone as DJ Omar Gosh
In the film’s climax, the final tournament commentators are joined by a flamboyantly dressed fictional celebrity, DJ Omar Gosh, played by none other than music star Post Malone, who remains unmistakable even through all that bling.
Eminem as Donald Jr.
Joe Flaherty played Happy’s biggest heckler Donald in the original film, and now his son, played by rapper Eminem, is back to take up the mantle.
Haley Joel Osment
The ’90s child star plays rival golfer Billy Jenkins, who sports a powerful swing like Happy.
Benny Safdie as Frank Manatee
A co-director on “Uncut Gems” alongside Sandler, Benny Safdie plays the main villain in “Happy Gilmore 2”: Frank Manatee, the halitosis-stricken mind behind Maxi Golf, a new stunt-based golf association intended to rival the long-established Tour Championship league. His inclusion is a knowing wink to fans of Sandler’s other works.
Ken Jennings as himself
While watching TV early on, Happy is surprised to see his name appear as an answer on an episode of “Jeopardy.” And who better to host the show than real-life game-show host Ken Jennings?
Cam’ron
The rapper makes an appearance as himself.
Kid Cudi
The rapper plays an FBI agent.
Margaret Qualley, Eric André, and Martin Herlihy
When he’s at a new low, Happy is grouped with three amateur golfers in what they think will be a game-changing golf lesson. They’re played by comedian and actor Eric André, “The Substance” star Margaret Qualley, and “Saturday Night Live’s” Please Don’t Destroy in-house sketch troupe member Martin Herlihy.
Guy Fieri
The Food Network star plays a character named Maxi Starter.
Sean Evans
The star of First We Feast’s iconic talk show Sean Evans plays himself.
Bobby Lee
Comedian Bobby Lee also plays himself.
Dan Patrick as Pat Daniels
The legendary sportscaster appears as the host of Sports Hole with Pat Daniels, who breaks the news of Happy’s drunken hijinks at the municipal course.
Kym Whitley as Bessie
The comedian plays an overenthusiastic friend of Happy’s.
Marcello Hernandez as Esteban
Another “Saturday Night Live” cast member, Hernandez plays a character named Esteban.
John Daley as himself
A real-life unorthodox golf legend known for his anti-establishment attitude, John Dayly, seems a perfect fit for the world of “Happy Gilmore.” We see him spending his retirement squatting in Happy’s garage, where he seems to fill a pseudo-uncle type role in Happy’s family.
Travis Kelce as the waiter
Kansas City Chiefs tight end and Taylor Swift’s boyfriend shows off his acting chops in a memorable scene that involves a shirtless Kelce, a jar of honey, and a very hungry bear.
Kelsey Plum and Andrew Watt
When Happy returns to the municipal golf course to test his swing after a decade of boozing and inactivity, he’s greeted by the course starters, who are played by WNBA star Kelsey Plum and Grammy-winning producer Andrew Watt, widely known for his work with legends like the Rolling Stones, Elton John, Ozzy Osbourne, and Pearl Jam, earning him the nickname “the Rock Hall of Fame whisperer.”
The Tour Championship golfers
Pro golfers Tony Finau, Will Zalatoris (who also played the caddy Happy chokes out in the original), Justin Thomas, Bubba Watson, Scottie Scheffler, Bryson DeChambeau, Rory McIlroy, and Brooks Koepka all play alongside Happy in the U.S. Bank Tour Championship. Scheffler, DeChambeau, McIlroy, and Koepka later join Happy to defeat the Maxi League golfers.
Tim Herlihy, Nelly Korda, and Nancy Lopez
On the parole board at the Westford State Mental Hospital that deems Shooter unfit for release is Drs. Hertz, Young, and Silver. They’re played by “Happy Gilmore” co-writer Herlihy, current #1 ranked golfer on the LPGA Tour Korda, and former LPGA superstar Lopez.
Veteran sportscasters
The longtime ESPN personalities Stephen Smith, Chris Berman, and Jim Gray appear as themselves.
Reggie Bush as 8 Ball
The Heisman Trophy winner and former NFL running back appears as the character 8 Ball.
Verne Lundquist
The legendary sportscaster returns in “Happy Gilmore 2” after appearing as a golf commentator in the original.
Sean Avery and Chris Chelios
The retired NHL stars play a pair of henchmen.
Rebecca Quin and Nikki Bella
The WWE wrestlers play characters named Flex and Medusa.
Fernando Marrero
The pro wrestler plays a character named Screech.
Boban Marjanovic
The former NBA cult favorite and “John Wick” actor makes a cameo as a zealous Happy Gilmore fan named Drago Larson, the son of the character played by the late Richard Kiel.
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