You probably remember him as the wide-eyed kid who saw dead people. Or maybe you know him as the voice of Sora from those Kingdom Hearts games that have about twenty different spin-offs. But in 2025, Haley Joel Osment did something nobody really saw coming: he stepped onto the green as a professional jerk in Happy Gilmore 2.
Honestly, the internet didn't know what to do with it at first.
When the news leaked that Osment was joining the cast of the Netflix sequel, the rumors were flying everywhere. Was he playing Happy’s long-lost son? Was he just a random guy in a bar? Nope. Adam Sandler and director Kyle Newacheck went a much more interesting route. They cast him as Billy Jenkins, a young pro golfer with a "monster swing" who basically represents everything Happy Gilmore hates about the modern, corporate version of the sport.
The Surprise of Billy Jenkins
If you've seen the movie, you know Billy isn't just a cameo. He's actually a major hurdle for Happy's comeback. While Christopher McDonald’s Shooter McGavin is busy recovering from a decades-long stint in a mental institute (yeah, that actually happened in the plot), Osment’s character fills that vacuum of arrogance.
Billy Jenkins isn't your traditional country club snob. He’s part of "Maxi Golf," a rival league created by the villainous Frank Manatee (played by Benny Safdie). This league is all about stunts, energy drinks, and being as loud as possible. It’s basically a mirror of Happy’s own chaotic energy from the 90s, but repackaged into a polished, obnoxious TikTok-era athlete.
Osment plays it with this weird, intense precision. You’ve got to give it to him—most people still associate him with "The Sixth Sense," but the guy has spent the last decade playing incredibly specific, often dark or eccentric characters in shows like The Boys and Wednesday. He brings that same "unhinged but controlled" vibe to the golf course.
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Why This Role Matters for Osment’s Career
A lot of child stars just sort of... vanish. Or they have a rough time and never quite make it back to the A-list. Haley Joel Osment didn't do that. He went to NYU, did theater, and quietly became one of the most reliable character actors in Hollywood.
Seeing him go head-to-head with Adam Sandler is a trip.
There’s a specific scene on the back nine where Billy Jenkins manages to actually out-drive Happy. It’s a huge moment in the film because, for thirty years, Happy’s whole "thing" was being the guy who hits it further than everyone else. When Osment’s character steps up and clears the green with a smirk, you can feel the shift in the movie. It’s not just a comedy beat; it’s a "passing of the torch" (or at least a theft of the torch) that makes the stakes feel real.
- Real-life Golf Skills: Interestingly, Osment isn't faking it entirely. He actually plays golf in real life and has participated in celebrity tournaments for years.
- The Look: They gave him a specific "Maxi Golf" uniform that looks like a neon energy drink threw up on a polo shirt. It’s ridiculous.
- The Dynamic: While Shooter McGavin was a classic 90s antagonist, Billy Jenkins is a very 2020s version of a "villain." He’s obsessed with the brand.
The Controversy Surrounding the Premiere
It wasn't all smooth sailing, though. If you were following the news in the summer of 2025, you might remember that the Haley Joel Osment Happy Gilmore 2 press tour was a bit rocky. Osment made headlines for some legal issues and a court-ordered rehab program right around the time the movie premiered in New York and LA.
He was incredibly open about it, though. In interviews, he talked about the pressure of the industry and how he was working through his personal stuff. Fans were surprisingly supportive. Maybe it's because we've watched him grow up on screen, or maybe it's just that people appreciate honesty these days. Either way, his performance in the movie didn't suffer for it. If anything, that slightly "on-the-edge" energy he had in real life translated perfectly into Billy Jenkins' frantic, high-strung personality.
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What Most People Get Wrong About the Sequel
There's this idea that Happy Gilmore 2 is just a nostalgia trip. People thought it would be a bunch of old guys sitting around talking about the "good old days."
It's not.
The inclusion of actors like Osment, Bad Bunny, and Margaret Qualley proves that Sandler wanted to make a movie that actually exists in the present. The "Maxi Golf" storyline is a pretty sharp satire of things like LIV Golf and the way sports are being disrupted by massive piles of cash. Osment is the face of that disruption.
He’s not trying to be the new Shooter McGavin. Nobody can be Christopher McDonald. Instead, Osment plays the "Prodigy Who Sold Out." He’s the guy who has all the talent in the world but uses it to sell "Maxi Energy" instead of respecting the game. It creates a great foil for Happy, who is now the "old guard" trying to protect the soul of the sport.
The Verdict on the Performance
Critics were actually pretty kind to Osment. While some people felt the movie was a bit too "busy" with cameos (Travis Kelce, Eminem, and John Daly all show up), almost everyone agreed that the core rivalry between Happy and the Maxi Golf team worked.
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Osment has this way of being incredibly annoying on screen without making you want to turn the movie off. That’s a hard balance. You want to see him get hit with a golf ball, but you also want to see what he’s going to do next. It’s a testament to his training. He treats a goofy Adam Sandler comedy with the same level of character work he’d bring to a Broadway play.
Moving Forward After the Fairway
So, what’s next? If you enjoyed seeing him in the sequel, you won't have to wait long for more. He’s already slated for a bigger role in the next season of Wednesday on Netflix, and there are whispers he might be doing more voice work for Disney soon.
But for a lot of us, Haley Joel Osment in Happy Gilmore 2 will go down as one of those "Oh, I didn't see that coming" moments that actually totally worked. It proved he can handle big-budget comedy just as well as he handles psychological thrillers or indie dramas.
If you haven't watched it yet, pay attention to the scene where he tries to teach Happy how to use a "gravity-assisted" putter. It’s pure comedic gold.
To get the most out of his performance, go back and watch his recent turn in The Boys or Poker Face right before you hit play on Happy Gilmore 2. You’ll see the range he’s developed over the years. It makes his turn as a bratty golf pro even more impressive when you realize how much he’s actually doing with the character under all that neon spandex.