You know that guy in every Adam Sandler movie? The one who isn't the star but somehow makes the whole thing feel like home? That’s Allen Covert. But if you grew up watching a certain hot-headed hockey player try to save his grandma’s house, you know him best as Otto.
He’s the homeless guy. The one washing windshields in the middle of traffic. The guy who ends up carrying Happy’s bags while wearing a filthy sweatshirt and a look of pure, unbothered zen. Honestly, Allen Covert in Happy Gilmore is the secret sauce of that entire 1996 classic.
Most people don't even realize he has a name. In the actual theatrical cut of the movie, nobody ever calls him "Otto." He’s just there. He’s the vibes. He is the human personification of the chaotic, "everyone is welcome" energy that defined the early days of Happy Madison.
The Mystery of Otto the Caddie
It’s kinda wild when you think about it. Covert plays the most loyal person in Happy’s life—the guy who literally sticks by him through the Waterbury Open and the final showdown with Shooter McGavin—and yet, his name only exists in a deleted scene and the end credits.
Why does he matter? Because Otto represents the heart of Sandler’s comedy philosophy. While the "country club" elites like Shooter look at a guy like Otto and see trash, Happy looks at him and sees a partner. He gives him a job. He treats him like a person. It’s that blue-collar, "us versus them" mentality that made the movie a massive hit.
And let’s be real: Allen Covert’s performance is subtle genius. He barely speaks, but his facial expressions during the "Gold Jacket, Green Jacket" sequence are legendary.
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What Really Happened with Allen Covert and Happy Gilmore 2
Fast forward to now. We’re in 2026. The sequel, Happy Gilmore 2, finally hit Netflix recently, and the first thing everyone did was look for the bearded caddie.
The news? It’s complicated.
For the longest time, rumors swirled that Covert was a lock for the sequel. He’s been Sandler’s right-hand man since they were classmates at NYU. He’s produced almost everything the guy has done. But when the movie actually dropped, fans noticed a glaring hole. Otto wasn't hauling clubs. Instead, we got a hilarious but different dynamic with professional golfer Will Zalatoris and even a caddie role played by Bad Bunny.
Basically, the movie gives us a quick "where are they now" explanation. In the world of the sequel, Otto is living in Switzerland for tax purposes. It’s a classic Sandler-style throwaway line that explains why the original caddie isn't on the bag this time around.
Why the Absence Felt So Loud
There’s a reason people were bummed. In the original, Covert and Sandler had this shorthand. You could tell they were real-life best friends.
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The reality of why Covert didn't have a massive on-screen presence in the sequel might be more personal than professional. Back in 2023, reports surfaced that Covert was taking a break from the industry to deal with a family situation. He even stepped away from his executive role at Happy Madison Productions.
That’s the thing about the "Sandler Verse." It’s not just a business; it’s a group of guys who have been together for thirty years. When one of them isn't there, the couch feels a little empty.
The Career of a Professional Best Friend
If you only know him from Happy Gilmore, you’re missing out on some of the weirdest, funniest deep cuts in comedy history. Allen Covert isn't just "the caddie."
- The Wedding Singer: He’s Sammy, the guy obsessed with "The Fonzie."
- Big Daddy: He’s Phil D'Amato, the guy who is constantly being "threatened" by a toddler.
- 50 First Dates: He’s Ten Second Tom. Honestly, that might be his most iconic role outside of Otto.
- Grandma's Boy: His only real leading role, which has become a massive cult classic for anyone who has ever worked in tech or played a video game.
Covert is the glue. He’s often a co-writer or a producer, helping shape the jokes that Sandler eventually delivers. He’s the guy who stays behind the scenes to make sure the "Happy Madison" brand stays consistent.
The "Dead Eyes" Legend
There’s a hilarious bit of Hollywood lore about Covert. Rumor has it that back in the day, studio executives didn't want him in Billy Madison because they claimed he had "dead eyes" on camera. Sandler, being the loyal guy he is, reportedly doubled down. He didn't just put him in the next movie; he made him a central part of the Happy Gilmore supporting cast.
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It was a middle finger to the suits. It was Sandler saying, "This is my guy, and he’s funny whether you like his eyes or not."
Is Otto Gone for Good?
While Happy Gilmore 2 moved in a new direction, the door isn't exactly slammed shut. Covert has started appearing at fan conventions again in 2024 and 2025. He’s been vocal about wanting to get back into R-rated comedies.
There’s even been talk about him starting his own production company. He’s currently working on a series called Meemaw with Roseanne Barr.
So, while Otto might be "in Switzerland" for now, Allen Covert’s influence on the world of Happy Gilmore is permanent. You can't replicate that 90s chemistry. You can't fake the look of a guy who actually enjoys being on a golf course with his buddies, even if he is supposed to be playing a homeless man.
Actionable Takeaways for Fans
If you're feeling nostalgic for that specific era of comedy, here's how to dive back in:
- Watch the Jack and Jill Cameo: Believe it or not, Covert actually plays Otto again in the movie Jack and Jill. It’s a weird crossover, but it’s the only other time the character officially appears.
- Check Out the Deleted Scenes: If you can find the original Happy Gilmore DVD extras, look for the scenes where Happy and Otto actually talk more. It adds a lot of layers to their friendship.
- Follow the New Projects: Keep an eye on Covert’s new ventures outside of Happy Madison. If he succeeds in bringing back the "theatrical R-rated comedy," we might get a spiritual successor to Grandma's Boy.
- Re-watch Grandma's Boy: If you haven't seen it, it's the peak of Covert's on-screen talent. It shows he was always more than just a sidekick.
The bond between Allen Covert and the character of Otto is a reminder of why we love these movies in the first place. It’s not about the golf. It’s not even really about the jokes. It’s about the people you bring along for the ride.