Adam Sandler knows how to crank out films with tons of cameos. The truth is that he doesn't always like asking people to be in his movies. He is afraid to bug them as they might be looking forward to having a new day. Then Sandler calls, and everything changes.
For anyone who has seen Happy Gilmore 2 on Netflix (or the original Happy Gilmore, or heck, nearly any Sandler film), you will know that there are dozens of cameos. Famous golfers appear, famous actors show up, and lots of musicians. Even Taylor Swift's boyfriend, Kansas City Chiefs tight end Travis Kelce, is in the film.
Bad Bunny plays Sandler's character's caddie, and he does a great job. So does Eminem, who only has one scene, but he chews it up and makes it great. The hip-hop icon plays Donald Floyd Jr., the son of Senior, the guy who kept heckling Happy in the first film by continuously calling him a "Jackass."
How Adam Sandler involved Eminem in Happy Gilmore 2
Donald Floyd, Sr. was played by Joe Flaherty, but Flaherty died in 2024 and could not reprise his character. Instead, Sandler gave Eminem (Marshall Mathers) a call as the two had been friends for decades and asked him to take a day out of his schedule to work on the film.
Sandler talked about the making of the film on a recent episode of The Dan Patrick Show, and specifically about how Mathers came to be involved. (As many know, Mathers has acted plenty of times before and was excellent in the film 8 Mile.)
Sandler said, "I love Eminem, I'm friends with Eminem, but I don't want to bother the man. And everybody kept saying, 'Man, Eminem would be so funny in this part.' And I was like, I don't want to ruin this guy's time, he's hanging out, he's in Detroit, he's doing his life, making records. I give him a call and say, 'Dude, I know it's a pain in the ass, but it's pretty funny. You mind shooting out to us for a day? And then he's like, 'Yeah, yeah, send me the stuff.'"
Donald Floyd, Jr. wasn't there to make up for how his father treated Happy Gilmore, however. Instead, Junior picked up where Senior left off and continued the chastisement of the golfer. Anything else would have been unfunny, and Sandler would not set up Mathers in that way.
Adam Sandler met Eminem after a 1999 episode of Saturday Night Live. Sandler was a member of the cast, and Mathers was there as part of the musical act. That also included Snoop Dogg and Dr. Dre. Ever since, Sandler and Mathers have been fast friends.