Hollywood is buzzing with the electrifying news of Eminem’s surprise cameo in Happy Gilmore 2, the long-awaited sequel to Adam Sandler’s 1996 cult classic, which dropped on Netflix on July 25, 2025. The Detroit rap legend, known for his lyrical genius and intense persona, made waves with a role that was finalized just one day before filming began—a chaotic, last-minute switch that has fans and insiders alike scrambling for the juicy details. Originally not slated to play the son of the iconic heckler Donald, portrayed by the late comedian Joe Flaherty, Eminem’s unexpected casting as Donald Jr. has sparked a frenzy of excitement and speculation. How did this happen? Why the sudden change? And what does it mean for the legacy of Happy Gilmore? Buckle up as we dive into the wild, star-studded saga of Eminem’s role in Happy Gilmore 2!

A Last-Minute Casting Coup

The story of Eminem’s involvement in Happy Gilmore 2 reads like a Hollywood thriller. According to sources close to the production, the decision to cast Marshall Mathers—aka Slim Shady—was a whirlwind move, finalized a mere 24 hours before cameras started rolling in New Jersey on September 9, 2024. Insiders reveal that the original plan for the character of Donald Jr., the son of Joe Flaherty’s unforgettable heckler from the 1996 film, was entirely different. While the exact details of the initial casting remain under wraps, it’s clear that Eminem wasn’t the first choice for the role. So, what changed?

Adam Sandler himself spilled some tea during an interview on The Dan Patrick Show in December 2024, admitting that he initially hesitated to “bother” his longtime friend Eminem with the offer. “I love Eminem, I’m friends with Eminem, but I don’t want to bother the man,” Sandler confessed. Yet, the persistent buzz from the cast and crew—who were convinced Eminem was perfect for the part—pushed Sandler to make the call. “Everyone kept saying, ‘He’d be great for this,’” Sandler recalled. “So, I reached out, and he was like, ‘I’m in!’” The result? A comedic performance that’s already being hailed as one of the sequel’s standout moments.

Paying Homage to a Comedy Legend

Eminem’s role as Donald Jr. is a heartfelt nod to Joe Flaherty, who passed away in April 2024 and left an indelible mark on Happy Gilmore fans with his portrayal of Donald, the obnoxious heckler hired by Shooter McGavin to throw Happy off his game. In the original film, Flaherty’s character famously shouted “Jackass!” during Happy’s swings, cementing the line as a comedic classic. In Happy Gilmore 2, Eminem steps into his father’s shoes—literally and figuratively—donning a bucket hat, wig, and beard to deliver a performance that’s both a tribute and a fresh twist.

Sporting an almost unrecognizable look, Eminem’s Donald Jr. picks up where his “dad” left off, taunting Happy Gilmore with the same iconic “Jackass!” insult during a pivotal golf tournament scene. “You jackass!” Eminem sneers, echoing Flaherty’s legacy while adding his own razor-sharp edge. The rapper even throws in a hilarious line about his father being “in the great Sizzler in the sky,” a callback to Donald’s love for the restaurant chain in the original film. Fans on X have been losing it over the moment, with posts like, “Eminem in Happy Gilmore 2 also yeah the internet’s going to have a field day with this one” (@FrostyzWRLD) and “#Eminem as always was hilarious, Go and watch” (@SonaShady8).

A Wild Scene and a Gator-Filled Fate

The cameo doesn’t stop at heckling. In true Happy Gilmore fashion, Eminem’s scene escalates into pure chaos. After Happy blows another shot, the two nearly come to blows, with Eminem boasting, “I know a lot about fighting. I’ll bite your leg off!” It’s a quintessential Slim Shady moment—brash, absurd, and dripping with attitude. But Happy, barred from fighting due to the risk of jail time, lets his four sons—Gordie, Bobby, Wayne, and Terry—take care of business. The boys, played by Maxwell Jacob Friedman, Philip Schneider, Ethan Cutkosky, and Conor Sherry, respectively, waste no time, hoisting Eminem’s character and tossing him into a nearby lake. What happens next? Let’s just say the alligators from the original film make a triumphant return, and Donald Jr. meets a grim, yet hilariously fitting, end. Even rapper Cam’ron, another cameo star, gets a kick out of watching Eminem get “torn up by the gators.”

This over-the-top sequence has fans buzzing about Eminem’s comedic chops. Director Kyle Newacheck called the scene “a challenge” but praised Eminem’s performance, saying he “performed it wonderfully.” Sandler echoed the sentiment, noting, “We just hung out all day with Eminem, and he just shot and shot. He was insane. There’s a million things we can use and a million that we’re glad we have him on tape.”

A Star-Studded Sequel

Eminem’s cameo is just one of many in Happy Gilmore 2, which boasts a jaw-dropping roster of celebrities, athletes, and Sandler regulars. Bad Bunny shines as Happy’s eccentric caddy, Oscar, while Post Malone pops up as the flamboyant DJ Omar Gosh. Kid Cudi plays an FBI agent, and Cam’ron appears as himself, adding to the film’s eclectic vibe. The golf world is well-represented too, with pros like Rory McIlroy, Bryson DeChambeau, Brooks Koepka, and Scottie Scheffler joining the fun, alongside legends like Jack Nicklaus and Lee Trevino. Travis Kelce even makes a splash as a mean-spirited waiter, a role that earned a shoutout from Taylor Swift on Instagram Stories, where she called the film “13/10” and referenced Kelce’s honey-covered scene with a cheeky emoji.

Sandler’s family also gets in on the action, with his wife, Jackie, playing a dance instructor, and his daughters, Sadie and Sunny, taking on key roles. The sequel, filmed across New Jersey from September to December 2024, is a love letter to the original, blending nostalgia with fresh faces. “It feels like there was an overwhelming ‘Yes,’” Newacheck said of the star-studded cast’s enthusiasm. “The love for this movie is unequivocal.”

Eminem’s Hollywood Comeback

For Eminem, Happy Gilmore 2 marks a rare return to the big screen. The rapper, who won an Oscar for “Lose Yourself” from 8 Mile in 2003, hasn’t been a Hollywood regular in recent years. His last notable role was a cameo as “White Boy Rick” in the 2021 series BMF. Fans were thrilled to see him back in action, especially in a comedy, where his quick wit and larger-than-life persona shine. His previous collaboration with Sandler in 2009’s Funny People proved their chemistry, and Happy Gilmore 2 takes it to another level.

The last-minute nature of Eminem’s casting only adds to the intrigue. Sources suggest the original actor for Donald Jr. may have dropped out due to scheduling conflicts or creative differences, though no official word has confirmed this. What’s clear is that Eminem’s involvement was a game-changer, bringing a dose of star power and unpredictability to the set. “He came in and was funny as hell,” Sandler gushed, hinting at hours of unused footage that could make for an epic blooper reel.

Honoring the Original’s Legacy

Happy Gilmore 2 doesn’t shy away from honoring its predecessor, especially the late stars like Flaherty, Carl Weathers (Chubbs), and Bob Barker. The film dedicates moments to their memory, with Eminem’s role serving as a direct bridge to Flaherty’s iconic performance. The sequel also tackles heavier themes, following Happy as a widowed, alcoholic ex-golfer trying to fund his daughter Vienna’s ballet school dreams. Yet, it retains the slapstick heart fans love, with absurd gags, heartfelt redemption, and, of course, alligators.

The Verdict

Eminem’s last-minute casting in Happy Gilmore 2 is the kind of Hollywood magic that fuels tabloid dreams. From a near-miss to a scene-stealing cameo, his role as Donald Jr. is a perfect blend of nostalgia, humor, and chaos. As the film dominates Netflix’s top 10, racking up 46.7 million views in its first three days, fans can’t get enough of Eminem’s “Jackass!” taunt and gator-filled demise. Will this spark a new wave of acting gigs for Slim Shady? Only time will tell, but for now, Happy Gilmore 2 has cemented its place as a cameo-packed triumph, with Eminem leading the charge.