What Celebrities Might Appear in Happy Gilmore 2?

Happy Gilmore fans have waited nearly 30 years for a sequel, and the pressure is on Adam Sandler to ensure it doesn’t disappoint when it arrives on Netflix in 2025.

The last time audiences saw Happy, he’d won the Tour Championship and helped save his grandmother’s house. The upcoming sequel will see him resurrect his golf career, facing some new and familiar faces along the way.

Christopher McDonald and Julie Bowen will reprise their roles as Shooter McGavin and Virginia.

Also, Benito Martinez Ocasio, known to music fans as Bad Bunny, has signed on to star in the film. NFL tight-end Travis Kelce and former pro golfer John Daly will have a cameo, too.

However, it is expected many more familiar faces will pop up in the flick. Read on for predictions about the celebrities that might appear in Happy Gilmore 2.

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Could Taylor Swift Make a Cameo?

On a May episode of his podcast New Heights, Travis Kelce admitted he lobbied for a cameo in Happy Gilmore 2.

Kelce said, “I’m a huge fan of the Sandman… I didn’t even know there was a job opening on Happy Gilmore 2. I’ll be a f*****g extra… anything to get around Happy Gilmore, an Adam Sandler film or set. Count me in.”

His passionate appeal paid off, as Sandler gave the Kansas City Chiefs star a small role in the upcoming sequel.

As Kelce is dating Taylor Swift, many fans hope the singer-songwriter will make a cameo in the golf comedy movie, too.

According to reports, Sandler hopes Taylor Swift will join Kelce on set, as his daughters are huge fans of the “Cruel Summer” star. As his kids have small roles in the film, he hopes they’ll have an opportunity to meet her, and he may even convince her to make a cameo, which would help the film tap into a new audience.

Sandler has confessed in the past that he’s a little bashful around the singer, admitting, “Because of what she means to my kids, I get a little jumpy around Taylor Swift. Just because I don’t wanna blow it for them. So, I’m a little like ‘Taylor Taylor,’ I talk a little too loud or something. I don’t stay as cool as I can.”

Might Will Zalatoris Appear as a Caddy?

Will Zalatoris, a professional American golfer, is a huge Happy Gilmore fan. He even has a quote from the movie engraved on his wedge, as it relates to his striking resemblance to Happy Gilmore’s caddie at Waterbury.

Sandler even sent the 28-year-old sports star a congratulatory message when close to his first major win three years ago, addressing Zalatoris as his caddie.

The golfer even claimed, “Out on the golf course, I’ll get some guy going ‘Where you going with these clubs, punk,” as Gilmore’s character believes the caddie is a thief. Seeing the funny side of the comparison, he carved “But Mr. Gilmore, I’m your caddie” on his wedge.

For this reason, Zalatoris appearing as a caddie in Happy Gilmore 2 could draw a laugh.

Could Ben Stiller Return as the Mean Hospital Orderly?

Many fans will remember Ben Stiller’s cameo as the mean hospital orderly in Happy Gilmore.

While Netflix hasn’t confirmed that the comedy actor will reprise his role, he has teased that he’ll make an appearance.

In August 2024, a fan asked on X, “Are we gonna see you again in Happy Gilmore 2?” and Stiller replied, “Warming the glass”.

The response refers to Stiller’s famous quote from the 1996 movie when he tells Gilmore’s grandmother she “can trouble me for a warm glass of shut-the-hell-up” after she requests a glass of warm milk.

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