
‘Happy Gilmore 2' ultimate cameo guide — from Haley Joel Osment to Post Malone
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.
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
Get instant access to breaking news, the hottest reviews, great deals and helpful tips.
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.
Follow Tom's Guide on Google News to get our up-to-date news, how-tos, and reviews in your feeds. Make sure to click the Follow button.
Hashtags

Try Our AI Features
Explore what Daily8 AI can do for you:
Comments
No comments yet...
Related Articles
Yahoo
2 hours ago
- Yahoo
Cameron Boyce's Mom Reacts to Adam Sandler's Happy Gilmore 2 Tribute
Originally appeared on E! Online Libby Boyce was touched by Adam Sandler's tribute to her son. Indeed, Cameron Boyce, who died in 2019 at age 20 after suffering a seizure in his sleep, makes a small appearance in the Saturday Night Live alum's new Netflix movie Happy Gilmore 2. 'Adam always finds a way to keep Cams memory alive,' Libby wrote on Instagram July 27, 'which warms our heart.' She went on to detail the friendship between Adam and Cameron, who starred together as father and son in the Grown Ups movies. 'Adam and Cameron talked quite a bit in the days leading up to his death,' Libby shared. 'Cameron was supposed to be in Hubies [sic] Halloween and they were strategizing. They had a bond I think related to being authentic, funny and just keeping it real.' E! News has reached out to Cameron's family for comment and has not yet heard back. While Adam's inclusion of Cameron in Happy Gilmore 2—a blink-and-you-miss moment of the then-teen star in one of his Disney Channel shows sneakily shown on a TV screen in the background—was celebrated by the family and fans online, it's not the first tribute Adam has paid to his former costar. More from E! Online Bryan Kohberger's Fellow Inmate Details His Unusual Behavior in Jail Jay-Z's Alleged Son Rymir Satterthwaite Drops Federal Lawsuit Jesse Metcalfe Responds to Scheana Shay's Memoir Detailing Their Romance Indeed, during the credits of his 2020 movie Hubie Halloween, the Billy Madison star honored Cameron with a heartfelt message. "In loving memory of CAMERON BOYCE," the tribute read, alongside a picture of the Descendants star. "Gone way too soon and one of the kindest, coolest, funniest, and most talented kids we knew. You live on forever in our hearts and are truly missed every day." Since his death, Cameron's mom has also regularly shared sweet memories of her son, including earlier this month near the sixth anniversary of his sudden passing. 'Cameron loved and felt dance on a deep level,' Libby wrote on Instagram July 11 alongside a picture of her son in a dance class. 'When I saw this pic, and I zoomed in, I recalled seeing on his face how comfortable and joyful he was whenever he danced.' Read on to learn about other notable former Disney Channel stars. Clayton Snyder, Lizzie McGuireAdam Lamberg, Lizzie McGuireLalaine, Lizzie McGuireJake Thomas, Lizzie McGuireCamilla Belle, Rip GirlsJake T. Austin, Wizards of Waverly PlaceDavid Henrie, Wizards of Waverly PlaceJennifer Stone, Wizards of Waverly PlaceMia Talerico, Good Luck CharlieBridgit Mendler, Good Luck, CharlieKiely Williams, Cheetah GirlsSabrina Bryan, Cheetah GirlsRyan Merriman, Smart HouseKirsten Storms, Zenon: Girl of the 21st CenturyErik von Detten, Brink!Raviv Ullman, Phil of the FutureKimberly J. Brown, HalloweentownMitchel Musso, Hannah MontanaJason Earles, Hannah MontanaKyle Massey, That's So RavenA.J. Trauth, Even StevensChristy Carlson Romano, Even StevensBrandon Baker, Johnny TsunamiAlana Austin, Motocrossed For the latest breaking news updates, click here to download the E! News App Solve the daily Crossword


Tom's Guide
3 hours ago
- Tom's Guide
Like 'Happy Gilmore 2?' Here's the 10 best Adam Sandler movies on Netflix, Prime Video and more
Adam Sandler is easily one of the biggest comedy stars in Hollywood, and the success of Netflix's newest original, "Happy Gilmore 2," shows audiences still can't get enough. Though critics have taken shots at him for decades, Sandler has built a devoted fanbase thanks to his relatable everyman charm and comedic chops. If "Happy Gilmore 2" has you eager to rewatch some of Sandler's greatest hits, we've got you covered. Several of Sandler's most iconic comedies like "The Water Boy" and "Punch-Drunk Love" are only available to rent or buy, but there are still plenty to find across the best streaming services — including some you can watch for free. So without further ado, let's dive into where you can watch all the best Adam Sandler comedies on Prime Video, Netflix, and more. "Billy Madison" is one of Sandler's earliest starring roles, and it ranks alongside "Happy Madison" as one of the comedian's most beloved earlier entries. He plays Billy, a pampered young heir to a massive hotel chain and the gold standard in man-child comedy. After wrecking an important dinner with his usual antics, his father, Brian Madison (Darren McGavin), decides to leave his empire to someone more responsible when he retires. Determined to prove himself, Billy convinces his father to give him one last chance with an absurd challenge: to return to school and pass all 12 grades. "Billy Madison" was another early entry that cemented Sandler's legacy of iconic characters and endlessly quotable one-liners. It's all a bit ridiculous, but given the wild premise, that's exactly what makes it so charming. "Big Daddy" is the perfect example of a movie that fell flat with critics but is still a favorite for Sandler fans. The 1999 comedy classic stars Sandler as Sonny Koufax, an unemployed law school grad coasting off a settlement from an accident payout. Get instant access to breaking news, the hottest reviews, great deals and helpful tips. To prove to his ex-girlfriend that he's ready to grow up, he 'adopts' a 5-year-old boy named Julian (played by twins Cole and Dylan Sprouse). Together, they get up to all kinds of mischief around Manhattan, but important life lessons manage to peek through all the mayhem. "Big Daddy" is Sandler in peak dad mode, and in retrospect, it feels like a midway point between his silly man-child roles and his more experimental and rom-com era to come. With blockbusters like "The Waterboy" and "Big Daddy" under his belt, Sandler unleashed one of his most bizarre films to date with "Little Nicky, a unique blend of dark fantasy with frat-boy humor. Sandler stars as the titular son of Satan (Harvey Keitel) and a radiant angel (Reese Witherspoon). When his two brothers scheme to claim the throne of the underworld by unleashing chaos on Earth, Nicky sets out to stop them. But that's a tall order for a hopelessly inept, emo-haired oddball with a speech impediment. "Little Nicky" was a critical and commercial flop that stalled Sandler's career momentum in his prime, but in the decades since, it's developed a cult following, largely thanks to Sandler's unhinged performance. With "Mr. Deeds," Sandler and his longtime collaborators, writer Tim Herlihy and director Stephen Brill, take on a remake of a Hollywood classic: the 1930s Frank Capra- and Gary Cooper-led film "Mr. Deeds Goes To Town." Some details have obviously changed, but "Mr. Deeds" keeps the general story intact. Lovable small-town pizza guy Longfellow Deeds (Sandler) gets the shock of a lifetime when he unexpectedly inherits his uncle's vast estate, including a grand mansion and media empire. As insiders within the company scheme to take him down, ambitious reporter Babe Bennett (Winona Ryder) sets out to get close to Deeds, hoping to land an exclusive story, but ends up getting more than she bargained for when sparks start to fly. When Sandler teamed up with screen legend Jack Nicholson for "Anger Management," it marked a turning point in his career. Sandler plays the mild-mannered Dave Buznik, who's sentenced to anger management after a misunderstanding on a flight spirals out of control. His life is turned upside-down when he's assigned to the unconventional (and increasingly invasive) therapist Buddy Rydell (Jack Nicholson), who moves in with him to provide hands-on treatment for his supposed anger issues. It's rare we see Sandler play the straight man for a change, and "Anger Management" stands out for Nicholson's larger-than-life performance and the surprisingly strong comedic chemistry the two share. Watch 'Anger Management' now on Tubi Considering the undeniable chemistry they had in "The Wedding Singer," it's a wonder it took Sandler and Drew Barrymore six years to reunite for another romantic comedy. But it was worth the wait for "50 First Dates." Sandler plays Henry Roth, a commitment-phobic marine veterinarian living in Hawaii. He meets his match with Barrymore's Lucy, a kind-hearted art teacher who suffers from short-term memory loss after a car accident. Every day, she wakes up thinking it's the same day, leaving Henry to win her over again and again, one meet-cute at a time. It's a quirky but sweet rom-com with all the classic Sandler touches you'd expect: a signature Sandler guitar song, Rob Schneider in a wildly over-the-top supporting role, and a scene-stealing walrus named Jocko. Watch '50 First Dates' now on Netflix Stepping into the cleats of Burt Reynolds, Sandler takes a surprisingly faithful approach to this remake of the 1974 classic "The Longest Yard." As Paul Crewe, a disgraced former NFL quarterback who lands behind bars after violating probation, Sandler blends humor with just enough heart to make the role his own while preserving the original's gritty yet entertaining tone. To entertain a warden, Paul attempts to lead a team of inmates onto the gridiron. But before he can put a squad together, he'll first have to earn the respect of his fellow prisoners. While it may not hit the same legendary status as the original, Sandler's version still scores — maybe not a touchdown, but a solid two-point conversion. Watch 'The Longest Yard' now on Hulu "Happy Gilmore" director Dennis Dugan and Sandler team up once more in "You Don't Mess with the Zohan," a wildly absurd comedy centered around an Israeli counterterrorism commando whose true passion is hairstyling rather than espionage. With an over-the-top love for hummus, an exaggerated wardrobe full of unbuttoned shirts, and a cartoonishly large bulge, Sandler tries to bring levity to a thorny subject. Like "Happy Gilmore," the film is also packed with unexpected cameos, from Chris Rock and Henry Winkler to Mariah Carey and, most bizarrely, Dave Matthews playing a clueless white supremacist. It all adds to the film's chaotic charm. Watch 'You Don't Mess with the Zohan' now on Hulu If you liked Sandler's more dramatic turn in "Uncut Gems" but are still looking for something with a healthy helping of laughs, "Hustle" deserves a spot on your watchlist. Sandler delivers a standout performance as Stanley Sugarman, a down-on-his-luck basketball scout for the Philadelphia 76ers who discovers an unpolished but gifted player, Bo Cruz (Juancho Hernangómez), while overseas. Stanley brings him to the U.S. with hopes that Bo will be picked up by the 76ers or another NBA team — and reboot his own career in the process. NBA fans will especially enjoy the many cameos from real players, past and present, but the film's emotional core and Sandler's performance make it resonate with audiences well beyond the sports world. Watch 'Hustle' now on Netflix It's nearly impossible to talk about Sandler's best movies without shouting out his standout romantic comedy "The Wedding Singer." Sandler stars as Robbie Hart, the eponymous singer who's left broken-hearted after his fiancée dumps him at the altar. Robbie's life takes a turn when he meets Julia Sullivan (Drew Barrymore), a waitress working many of the same gigs. As fate would have it, Julia is also engaged, setting the stage for a romantic dilemma. Uncharacteristically sweet for a '90s Sandler film, "The Wedding Singer" marked his first of many collaborations with Barrymore. While the plot hits a lot of familiar tropes, it's the winning combination of comedy and chemistry between Sandler and Barrymore that makes this film shine. Watch 'The Wedding Singer' now on Tubi Follow Tom's Guide on Google News to get our up-to-date news, how-tos, and reviews in your feeds. Make sure to click the Follow button.


Tom's Guide
4 hours ago
- Tom's Guide
5 top new movies to stream this week on Netflix, HBO Max, Hulu and more (July 29-Aug. 4)
This week offers plenty of new movie options across the best streaming services, from a post-apocalyptic zombie thriller to a romantic drama set at a storied English university. Whatever sort of movie you're in the mood for, there's likely a newcomer to suit your tastes. '28 Years Later' on PVOD platforms headlines the next seven days, but HBO Max subscribers will be eager to enjoy the blood-soaked thrills of 'Final Destination Bloodlines' while over on Netflix, get your tissues out, because 'My Oxford Year' looks like a tearjerker. Looking to watch something fresh? These are the top new movies landing across streaming services over the next few days. And if you want to binge-watch, here's a guide to all the best new TV shows this week. The old saying goes, 'Time heals all,' but in Danny Boyle's apocalyptic zombie-infested Britain, that's not the case. This long-awaited second sequel to '28 Days Later' takes place almost three decades after the Rage Virus turned the U.K. into a quarantine island cut off from the rest of the world, and things have not improved in the time since Cillian Murphy's Jim was wandering around a devastated London. If anything, the situation has only gotten worse. On a remote, well-fortified island just off the mainland, Jamie (Aaron Taylor-Johnson) lives with his son Spike (Alfie Williams) and ill wife Isla (Jodie Comer). Taking his son on a rite-of-passage trip to the zombie-plagued mainland, Jamie and Spike discover the infected have mutated to become even deader, and that there are additional threats to consider. Also starring Ralph Fiennes and Jack O'Connell, '28 Years Later' successfully recaptures the spirit and visual style of the 2002 original and, aside from a tonally confused ending, is an extremely compelling watch. Get instant access to breaking news, the hottest reviews, great deals and helpful tips. Plus, it features more than a few references to my beloved Newcastle Utd soccer team and is set in North East England (which happens to be my birthplace), which makes it an instant must-watch in my books. Buy or rent on Amazon from July 29 Mike Flanagan has developed a reputation as a horror master after directing movies like 'Oculus," "Gerald's Game" and 'Doctor Sleep,' alongside helming chilling Netflix shows 'The Haunting of Hill House' and 'Midnight Mass." However, he trades his usual spooky approach for something a little more heartwarming with 'The Life of Chuck.' This fantasy drama has been described as 'life-affirming' and has even been mooted as a potential awards contender in the upcoming season. Based on the novella of the same name by Stephen King, it marks the third time Flanagan has adapted one of the legendary author's works for the big screen, and stars Tom Hiddleston as the eponymous Charles 'Chuck' Krantz. The movie is told in reverse chronological order as we follow Chunk from his adulthood through to his younger years as he experiences all the ordinary things that make life truly extraordinary. The well-received movie also stars Chiwetel Ejiofor, Karen Gillan, Jacob Tremblay and Mark Hamill. Buy or rent on Amazon from July 29 'Final Destination Bloodlines' marks the return of the long-running horror franchise, and it's an excellent revival. I'd argue it ranks among the very best of 'Final Destination' movies ever, keeping the classic formula intact but with new twists that only add to the blood-soaking mayhem. Following the series' longest premonition scene to date, we flash forward more than 50 years and meet Stefani (Kaitlyn Santa Juana), a college student haunted by a grisly vision of a skytower collapsing in the 1960s. Soon enough, death begins stalking Stefani and her family, and the secret to survival might just be locked in her grandmother's past. The overly complicated death sequences have always been the main appeal of the 'Final Destination' franchise, and 'Bloodlines' packs some of the most darkly funny ones to date. And while it doesn't completely reinvent the wheel, it does take a few risks that all play off very well. It also marks the final on-screen appearance of franchise mainstay Tony Todd, who delivers a memorable last performance that might just have you shedding a tear or two. Watch on HBO Max from August 1 If you're looking for a gooey romantic comedy-drama in the vein of 'The Life List,' then Netflix has you covered this week with 'My Oxford Year.' Yes, the release timing is a little odd — a romance tale set in rainy England feels perfect for the fall — but still, I have no doubts this movie will prove popular with Netflix subscribers, even if critics might tear it to shreds. Based on the novel of the same name by Julia Whelan, it centers on Anna De La Vega (Sofia Carson), an American student who fulfills her lifelong dream of studying at England's prestigious (and pretentious) Oxford University. By all accounts, her life is going exactly to plan, but her carefully-considered plan is thrown into turmoil when she meets a very charming British boy (Corey Mylchreest) and sparks fly. Guaranteed to be full of sappy dialogue and overly dramatic musings about seizing the moment while you can, 'My Oxford Year' clearly knows its audience and plays to it. Watch on Netflix from August 1 Hulu's big addition this week is a historical action epic that tells the story of William Tell, a Swiss folk hero, who was an important player in the country's attempts to fight against Austrian invaders in the 14th century. Directed by Nick Hamm and starring Claes Bang in the titular role, this cinematic spin on the legend opens with Tell, a former soldier in the Crusades, living as a huntsman. When the Austrian Empire marches into his country, he refuses to bend the knee and instead becomes part of a revolution that seeks to push back against these foreign oppressors. Also starring Connor Swindells, Golshifteh Farahani, Rafe Spall, Jonathan Pryce and Ben Kingsley, on the surface 'William Tell' looks like it has all the ingredients to be a 'Braveheart' for a new generation. Unfortunately, its critical reception was anything but epic. With a lengthy 134-minute runtime, 'William Tell' might only be one for genre obsessives. Watch on Hulu from August 1