‘I Was A Little Tipsy’: The Funny (And Sweet) Story Behind Adam Sandler And Bad Bunny Meeting For The First Time Before Happy Gilmore 2
The two had a real-life "meet cute."

After nearly 30 years of waiting, the highly anticipated Happy Gilmore 2 has finally landed on the 2025 movie schedule for anyone with a Netflix subscription. The flick is stuffed full of great callbacks and cameos, one of which is Bad Bunny as Gilmore’s new golf caddy, Oscar Mejías. The two have undeniable hilarious chemistry on screen, and now they’re sharing the funny and sweet way the two A-listers met the first time, before Happy Gilmore 2.
In a clip posted to the official YouTube account of Late Night with Seth Meyers, the two dished about how they met. According to the two prolific stars, in their own right, they made eye contact at an LA Lakers game. Adam Sandler set the stage, telling the host:
I was with my daughter, and she started hitting me. She’s going, ‘That’s Bad Bunny. That’s Bad Bunny.’ I go, ‘Where, where, where, where?’ And then we locked up eyes, and I gave you some love across the court.
For Bad Bunny, things were a bit more emotional. The Puerto Rican musician added that, besides being a bit inebriated, he was overwhelmed by the SNL alum knowing who he was. As he hilariously told it:
I was a little tipsy, and I was — Oh my god, I was with my best friend. [I was like,] ‘Oh my god, Jamon. He’s here.’ Because I was waiting for that moment. I’ve been in a lot of Laker games. I saw every celebrity but never Adam Sandler…. When he [made] eye contact with me, I cried. I did hold my tears like, ‘No, no I can’t. I can’t cry here on courtside. So I was like, ‘No, no way. He knows who I am.’
Sandler was lit with excitement and shock, not realizing how pumped Bad Bunny was. It looks like Bad Bunny had to work hard to keep it together in that moment. Check out their full exchange in the video below!

Bad Bunny isn’t just moonlighting on screen—he’s owning it. His turn as Oscar, Happy Gilmore’s new caddy, is way more than a stunt cameo. He’s magnetic, weirdly charming, and somehow hilarious without needing to say much at all. That might be the real trick: how someone can make a single word—“Breadsticks?”—a recurring punchline that keeps landing harder each time. It’s subtle, dumb in the best way, and entirely his own.
And then there’s Oscar’s cousin, Esteban (played to perfection by SNL standout Marcello Hernandez), whose brief appearance as a would-be caddy spirals into a rapid-fire bit of absurd generosity. It’s pure comic gold—the kind of throwaway gag you’ll find yourself quoting a week later.
I expected Happy Gilmore 2 to be a fun ride full of nostalgia and slapstick—and sure, there’s plenty of both, maybe even a little too much fan service at times. What I didn’t expect was the emotional gut punch. Between the laughs and callbacks, the film quietly explores grief and legacy, honoring the actors who’ve passed since the original. Carl Weathers’ death in particular allegedly reshaped parts of the script, and those rewrites carry real weight. There’s a moment where the tribute is so heartfelt, so sincere, it hit me like I’d just seen the man courtside in real life. It’s a sequel that knows when to swing for the heart, not just the cheap shot.
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If you’re a fan like I and Bad Bunny, of Adam Sandler and Happy Gilmore more specifically, then you’re in luck. Gilmore 2 is a fun sequel that respects its core audience and has a ton of laughs.
It’s pretty funny that Bad Bunny and Sandler first crossed paths courtside, with one of them a little tipsy and the other focused on his daughter. That unexpected moment kind of captures what Happy Gilmore 2 is all about: mixing laughs with some real feels, giving a nod to the past while making room for new stuff.

Ryan graduated from Missouri State University with a BA in English/Creative Writing. An expert in all things horror, Ryan enjoys covering a wide variety of topics. He's also a lifelong comic book fan and an avid watcher of Game of Thrones and House of the Dragon.
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