A Guide to Every Cameo in Happy Gilmore 2

30 years have passed since the unexpected golf champion Happy Gilmore (Adam Sandler), who was previously an unsuccessful hockey player, shocked everyone by defeating professional golfer Shooter McGavin (Christopher McDonald) in the 1996 Tour Championship. This victory earned him his first gold jacket and allowed him to reclaim his cherished grandmother’s house.

Currently, Sandler is set to reprise his character as the passionate yet endearing Happy in “Happy Gilmore 2”, a highly anticipated sequel that delves into what has become of him over the past three decades. It’s important to note that things haven’t been smooth sailing for Happy since he tragically struck and lost his loving wife Virginia (Julie Bowen) due to one of his powerful golf swings, leaving behind their four sons, Gordie, Bobby, Wayne, and Terry, as well as their daughter Vienna (Sunny Sandler), without a mother. Stricken with grief, Happy turned to alcohol, ran out of money, and even lost his late grandmother’s house. Today, he’s a mere shadow of his former self. However, when he decides to get back into golf in an effort to gather enough winnings for Vienna’s expensive ballet school, it thrusts him into a confrontation with shady businessman Frank Manatee (Benny Safdie), the mastermind behind a sensational new golf league called Maxi Golf, and Manatee’s enhanced star player Billy Jenkins (Haley Joel Osment).

Originally, Happy Gilmore wasn’t highly praised by critics, but it has become one of the most beloved ’90s comedies-cum-sports films. Given this popularity, it’s no surprise that a host of comedy greats, well-known sports personalities, and other distinguished figures have shown interest in the sequel.

Here, in order of appearance, are all the cameos in Happy Gilmore 2, now streaming on Netflix.

Steve Buscemi

When Grandma’s old house, which Happy had lost once before after Virginia’s passing, was lost again, he and Vienna were compelled to relocate to a less desirable part of town. There, they had an unwelcome neighbor, portrayed by Sandler’s long-time collaborator Buscemi (who has starred in over 15 of Sandman’s films), who frequently watched their doings with a watchful eye.

Jackie Sandler

In real life, Sandler’s spouse assumes the position of the dance instructor Monica at Vienna’s Boys & Girls Club. Through her efforts, she manages to secure Vienna a prestigious placement at the Paris Opera Ballet School by sending a video showcasing Vienna’s dancing skills.

Ken Jennings

In a short appearance similar to his role as host, Alex Trebek appears when Vienna plays a clip from Jeopardy! where Ken Jennings reads a clue about Happy. The clue goes like this: “With his extraordinary long drives and hockey player’s temper, this golfer won the first of his six Tour Championships in 1996.

Unfortunately, the contestants were left baffled as they repeatedly failed with their guesses “Happy Goldberg”, “Happy Gudenstein”, and “Skippy Goldenbaum” in rapid succession.

John Daly

In the realm of “Happy Gilmore,” it’s quite plausible that the unconventional golf icon Daly, a beloved figure from reality who revolutionized professional golf with his daring style and rebellious spirit, would opt to spend his retirement in Happy’s garage.

Kelsey Plum and Andrew Watt

When Happy goes to the municipal golf course to try out his swing again after a ten-year hiatus filled with inactivity and drinking, the staff on duty are none other than WNBA star Plum and Grammy-winning record producer Watt. Known for his collaborations with artists like the Rolling Stones, Elton John, Ozzy Osbourne, Pearl Jam, and many others, Watt has even earned the nickname “the Rock Hall of Fame whisperer.

Margaret Qualley, Eric André, and Martin Herlihy

At the local golf course, Happy finds himself paired with three amateurs who believe that one lesson at Golf Hut could significantly improve their game. These players are portrayed by Qualley (from The Substance), comedian André, and Herlihy, a member of Saturday Night Live’s in-house sketch group, Please Don’t Destroy.

Dan Patrick

In the fictional show “Sports Hole with Pat Daniels“, the character portrayed as the host, who spreads the gossip about Happy’s intoxicated antics at the local golf course, is actually modeled after sportscaster and radio personality Patrick, the genuine host of “The Dan Patrick Show“.

Tim Herlihy, Nelly Korda, and Nancy Lopez

The panel overseeing Shooter’s potential release from the Westford State Mental Hospital, who have declared him unsuitable for release, consists of Drs. Herlihy (known as a co-writer of the movie “Happy Gilmore”), Korda (the current top-ranked golfer on the LPGA Tour), and Lopez (a former star in the LPGA).

Jonathan Loughran

For several years, Loughran has been part of Sandler’s movie crew. He appears in the film as the character known as “the crazy eye orderly,” who eventually grants Shooter freedom following his 29-year confinement in a psychiatric facility.

Sadie Sandler

As a movie enthusiast, I can’t help but share that the character of Charlotte, who stands as Happy’s key ally in the Healing Alkies for Life (H.A.L.) alcohol treatment program, is portrayed by none other than Adam Sandler’s grown daughter, Sadie. It’s quite evident that Sandler cherishes family ties deeply.

Kym Whitley

In a more casual and relatable manner, we could say: Bessie, the overzealous participant in H.A.L.’s support group who often forgets about anonymity, is portrayed humorously by comedian Whitley.

Ben Stiller

In the second movie, Stiller once again takes on the role of Hal L, a retirement home orderly-turned-leader of an addiction support group. As before, he uses physical labor as therapy for himself and others. Now, you’re stepping into his universe, welcome to it, Happy.

Alix Earle, Sean Evans, Bobby Lee, Andrew Santino, Cam’ron, and Treasure Wilson

In these real-life shows – Hot Mess, Hot Ones, Bad Friends, and Talk with Flee – the hosts invited Manatee to appear as a guest while he was promoting Maxi Golf during his promotional tour.

Paige Spiranac

In the brief scene, professional golfer and model Spiranac is shown working at Dick’s Sporting Goods under the name Wendy. Here, she assists Happy in selecting some brand-new golf clubs.

Blake Clark

Clark, a frequent collaborator of Sandler, appears as an elderly gentleman on the beach, poorly contributing to Happy’s training regimen.

Jon Lovett

At the driving range, “dapper man” Lovett’s shots are repeatedly undermined by Happy, who keeps crushing Lovett’s golf balls with his harder hits.

Dennis Dugan

In the upcoming sequel, it’s once again Dugan who takes on the role of tournament commissioner Doug Thompson – the same man who directed the original “Happy Gilmore”.

The Tour Champions Dinner pros

In abundance throughout “Happy Gilmore 2” are cameos from professional golfers. During the Tour Champions dinner scene, former champions such as Fred Couples, Nick Faldo, Jack Nicklaus, Corey Pavin, and Lee Trevino (famous for his beard like Grizzly Adams in the original) can be seen at or near Happy’s table. Additionally, current players like Jordan Spieth, Xander Schauffele, Rickie Fowler, Keegan Bradley, and Collin Morikawa are also present in the room.

Travis Kelce

In a fun twist, Kansas City Chiefs’ tight end and Taylor Swift’s partner, Travis Kelce, demonstrated his thespian skills by portraying an over-the-top waiter at the Tour Champions Dinner. This character was determined to wow the golfers with his flamboyant performance.

Bad Bunny

As a film enthusiast, I can’t help but notice that Oscar, the former busboy-turned-caddy, is not just a fleeting appearance in this movie, but a significant character. Interestingly enough, he’s portrayed by none other than Benito Antonio Martínez Ocasio, also known as Bad Bunny, the worldwide sensation of reggaeton music.

Verne Lundquist and Jack Giarraputo

Again, sports commentator Lundquist teams up with his fictitious counterpart Jack Beard (portrayed by Happy Gilmore’s producer Giarraputo) as they reunite to provide commentary for the Tour Championship.

The Tour Championship golfers

In the U.S. Bank Tour Championship, professional golfers Tony Finau, Will Zalatoris, Justin Thomas, Bubba Watson, Scottie Scheffler, Bryson DeChambeau, Rory McIlroy, and Brooks Koepka team up with Happy. Later on, Scheffler, DeChambeau, McIlroy, and Koepka band together with Happy to face off against the golfers from the Maxi League.

(In this version, I’ve replaced “the caddy Happy” with simply “Happy,” as it is clear from context that Happy is a person, not an object. I also clarified their actions by stating they team up and then band together against another group.)

Kevin Nealon

In the initial film, Gary Potter, a former classmate of Nealon’s and the one who suggested he “send it” with their golf balls, seems to be currently employed as a reporter covering the Tour Championship.

Rob Schneider

In an upgraded version of Happy’s imagined sanctuary, Schneider assumes the part of the trike-riding cowboy and encourages Happy with a performance of his iconic “You can do it!” from the movie The Waterboy, yet another cherished production by Sandler.

Marcello Hernandez

Cast member Hernandez takes part in the festivities, portraying Oscar’s quirky relative Esteban. He even offers to get hit with golf balls by the experts during a practice session.

Stephen A. Smith

Sports analyst Smith, known for his flamboyant commentary, steps into the spotlight to share his thoughts on Happy’s surprising two-day triumph and subsequent three-day setback at the Tour Championship.

Boban Marjanović

In the original film, a revised sequence introduces Drago Larson, the son of Happy’s former construction boss Mr. Larson (played by Richard Kiel). This character reappears in support of Happy during a race, and interestingly enough, his mother Judy is portrayed by Adam Sandler’s own mom, who shares the same name.

Robert Smigel

In the continuation of the captivating tale, it’s me who’s thrilled to share that the very same character from Smigel’s IRS agent saga, known for his dramatic encounters including repossessing Happy’s grandma’s house and a memorable glass door incident, makes a comeback in the sequel. This time, he switches roles and appears as a lawyer, stepping into the courtroom to defend Happy when he faces troubles at the Tour Championship.

Lavell Crawford

In this rephrasing, comedian Crawford is portrayed as Slim Peterson, a character who steps into the scene. Slim is the son of Happy’s former mentor Chubbs, played by the late Carl Weathers, in the storyline. Interestingly, Slim also sports an artificial hand, and he aids professional golfers participating in the Tour Championship as they strive to outperform their rivals from the Maxi golfing group.

Post Malone

At the Maxi Tour Challenge, popular rapper Post Malone steps into the role previously held by DJ Omar Gosh as one of the three commentators, joining longtime announcers Verne Lundquist and Jack Beard.

The Maxi League golfers

Besides Billy, Manatee’s colorful lineup of Maxi League competitors also includes Harley (played by Oliver Hudson), Screech (portrayed by Fernando Marrero), 8 Ball (former football player Reggie Bush), Flex (professional wrestler Rebecca Quin), and Medusa (professional wrestler Nikki Garcia).

Guy Fieri

At the beginning of the Maxi Tour Challenge, there’s no doubt about it – it’s Guy Fieri from Food Network! Who else could it possibly be?

Eminem

When I see that Happy and his expert teammates are giving us a tough fight, I decide it’s time to bring in some reinforcements. So, I summon the spirited character played by the late Joe Flaherty’s son, who was known for his connection with Shooter and his fondness for Sizzler – let’s call him Eminem. With a fierce yell of “Jackass!”, he enters the scene just as Happy’s boys fling him into a treacherous water hazard teeming with alligators.

2025-07-25 21:06