‘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
Cosmopolitan
27 minutes ago
- Cosmopolitan
‘Perfect Match' Season 3 Release Schedule
Get ready for a summer of love, as Netflix's Perfect Match season 3 is on the way. The new episodes will kick off on Friday, August 1, with the new cast of singletons, including Love Is Blind US and Love Is Blind UK stars AD and Ollie, heading to the villa in search of love—and power. Here, they'll meet reality TV stars from the worlds of Too Hot to Handle and for the first time ever, the Netflix show is opening its doors to former The Bachelor and Love Island stars. They'll go to head-to-head in a series of challenges, and at the end one couple will be crowned this year's winners and will jet off on their all-expenses paid baecation. As we get ready for all the drama to begin, here's a full release schedule, so you don't miss a moment. Perfect Match season 3 starts on Netflix on Friday Aug. 1. The first batch of episodes will be available to stream from 12 am PDT/ 3 am EDT. Not, in the US? Here's all the times the first six episodes will land on Netflix where you are on 1st August: There are 10 episodes in total, and they'll be released weekly in batches, giving viewers time to catch up over the week. Below is a full release schedule: Perfect Match season 3 starts on Netflix on Friday 1st August.
Gizmodo
an hour ago
- Gizmodo
Roku's 2025 Streaming Stick Is Going for Practically Nothing While Amazon Fire TV Prices Stay Put
Traditional cable doesn't always cut it anymore, especially when your favorite content is spread across different streaming platforms and apps. Smart TVs are one option, but not everyone wants to spend hundreds on replacing a perfectly good screen. This is where a streaming stick can help, and Roku, one of the top names in streaming, has its HD stick at an unbelievable discount. Right now, you can grab Roku's latest HD streaming stick at Amazon for just $19, down from its usual price of $30. That's a 37% discount, and the easiest way to bring smart streaming functionality to any TV without spending a ton. Just hurry, since discounts this good usually don't stick around for long. See at Amazon This compact stick offers access to all popular streaming platforms, including Netflix, Hulu, Disney+, Prime Video, and Apple TV+. Whether you're planning to finally binge the second season of Severance (guilty) or just want some good old reality TV for background noise, it's all there. Need to stay updated on what's happening around the world, too? You also get 500+ free live TV channels with news, sports, and more, without needing any extra subscriptions. Setting it up is straightforward – plug it into your TV's HDMI port, and connect it to WiFi. You will be all set to personalize your experience in minutes. The included remote makes everything easy to navigate, and when you're not in the mood to click around, the built-in mic lets you use your voice instead. This mighty stick is tiny but lets you take your TV setup with you wherever you go (minus the actual TV). Plug it into another screen, and you'll have access to all your apps and preferences just like before. No additional setup needed, and a great way to feel at home anywhere around the world. It also plays well with smart home systems like Alexa, Google Home, Apple AirPlay, and HomeKit. So if you're already using one of those, it's even easier to control your TV through voice or your phone. Long story short: This streaming stick offers a great way to make any TV feel smarter, and it's also ideal for anyone looking to finally cut the cord. For just $19, you're getting a decent amount of features with a whole lot of convenience. You will never be out of options to watch, again. The deal just might not be around for too long, so grab it while you can. See at Amazon
Yahoo
2 hours ago
- Yahoo
Netflix Says Goodbye to Meghan and Harry's $100 Million Deal — Here's What's Next for the Royals
Netflix Says Goodbye to Meghan and Harry's $100 Million Deal — Here's What's Next for the Royals originally appeared on Parade. Netflix will not be extending its multi-year content partnership with Prince Harry and Meghan Markle, ending one of the streaming giant's most high-profile and heavily scrutinized deals. The agreement, reportedly valued at $100 million, will expire in September 2025, according to multiple outlets. The Duke and Duchess of Sussex signed the deal in 2020 following their departure from official royal duties and relocation to California. Through their production company, Archewell Productions, the couple was granted creative freedom to develop programming focused on mental health, social justice, and lifestyle. Over the course of the five-year agreement, the couple released five projects — most notably Harry & Meghan, their 2022 docuseries, which remains Netflix's most-watched documentary debut and drove high subscriber interest upon release. Other titles include Live to Lead, the animated project Pearl (later canceled), the documentary Heart of Invictus, and Meghan's lifestyle series With Love, Meghan. According to Netflix's Engagement Report released on July 17 — which covers the first half of 2025 — With Love, Meghan, which debuted in March, ranked No. 383 with 5.3 million views thus far. Another recent release, Polo, executive produced by the couple, ranked No. 3,436 with 500,000 views. While With Love, Meghan reached the global Top 10 on the week of its debut and performed well in select markets, it did not maintain high engagement over time. Season two of the series, which has already been filmed, will still premiere on the platform this fall. 'There's no animosity from either side. Things have just run their course," a source told The Sun. 'Netflix were clever in that they got a hell of a lot of viewers for the first documentary series, and knew, realistically, it would prove the zenith of content from the Montecito pair. The content got weaker from there on but, frankly, for £20million a year, anything was better than nothing." That being said, the source continued: 'Netflix [feels] they've got all they can from the couple." A Hollywood insider confirmed to People that the non-renewal reflects a broader shift in Netflix's content strategy, which is moving away from large, multi-year talent deals in favor of more flexible, project-specific arrangements. This is in line with recent changes to other high-profile partnerships, such as with Barack and Michelle Obama's Higher Ground production company. Their initial multi-project deal has transitioned into a first-look agreement. Still, the end of the Sussexes' exclusive Netflix partnership doesn't necessarily mark the end of their relationship with the platform. According to Page Six, the couple is expected to sign a first-look deal with Netflix once the current agreement expires, which would allow the streamer to have early access to future pitches without being locked into exclusive content production. The Duke and Duchess have not commented publicly on the deal's conclusion as of Wednesday morning. Markle, however, continues to promote her As Ever lifestyle brand, which launched in parallel with With Love, Meghan. Netflix Says Goodbye to Meghan and Harry's $100 Million Deal — Here's What's Next for the Royals first appeared on Parade on Jul 23, 2025 This story was originally reported by Parade on Jul 23, 2025, where it first appeared. Solve the daily Crossword
