You know the face. That slightly bewildered kid with the bleached, mushroom-cloud hair standing next to a guy trying to drive a golf ball into orbit. Or maybe you're thinking of the scruffy, homeless man washing his hair in a pond while holding a bag of clubs.
When people talk about the happy gilmore caddy, they’re usually talking about two very different people who helped define the vibe of the 1996 classic. It’s kinda wild how much these minor characters stuck in our collective memory. Most people just remember the "Mr. Gilmore, I’m your caddy!" line, but the story behind the actors is actually a lot more interesting than the slapstick on screen.
The Mystery of the "Waterbury Caddy"
Let’s start with the kid. His name is Jared Van Snellenberg.
In the original film, he plays the unnamed "Waterbury Caddy" who gets absolutely manhandled by Happy. He was only 14 at the time. Honestly, the most iconic thing about him wasn't even the acting—it was that hair. It was a rock-hard helmet of hairspray and bleach that his mom actually told him not to get. Turns out, defying his parents was the best career move he ever made, because Adam Sandler loved the look.
But here’s where it gets weird. If you look at him today, you won't find him on a movie set.
From the Fairway to the Lab
Jared basically quit acting to become a neuroscientist. Yeah, for real. He’s now Dr. Jared Van Snellenberg, an associate professor of psychiatry at Stony Brook University. He spends his days researching schizophrenia and using fMRI to study brain patterns.
👉 See also: The Real Story Behind I Can Do Bad All by Myself: From Stage to Screen
It’s a bizarre trajectory. One minute you’re getting shoved into the dirt by a fictional hockey-player-turned-golfer, and the next you’re a world-class expert on cognitive neuroscience. He’s gone on record saying he doesn't even play golf. He never did. He just happened to be a kid in Vancouver with the right hair at the right time.
The Other Happy Gilmore Caddy: Otto
Then there’s Otto.
Otto is the homeless man who takes over the bag once Happy hits the professional tour. He’s played by Allen Covert. If you’re a Sandler fan, you know Covert. He’s the ultimate "Sandler regular." He’s been in almost everything, from The Wedding Singer to 50 First Dates, and he even starred in Grandma’s Boy.
In the context of the happy gilmore caddy lore, Otto represents the "Happy Madison" philosophy: hiring your best friends and giving them the weirdest roles possible.
Covert’s performance as Otto is pure 90s Sandler comedy. He’s the guy who pockets a quarter used as a ball marker and treats the golf course like a public laundromat. It’s gross, it’s silly, and it’s exactly why the movie works. It balances the high-stakes world of professional golf with a guy who has literally no idea what a sand wedge is.
✨ Don't miss: Love Island UK Who Is Still Together: The Reality of Romance After the Villa
Why the Caddy Doppelgänger Changed Everything
For years, the internet had this running joke about PGA Tour pro Will Zalatoris.
Zalatoris looks exactly like the original kid caddy. The resemblance is so uncanny that it became a massive meme in the golf world. People were tagging Adam Sandler in photos of Zalatoris at the Masters, and eventually, Sandler leaned into it. He tweeted at Zalatoris, calling him a "young man" and saying Mr. Gilmore was proud of him.
This wasn't just a fun Twitter moment. It actually influenced the 2025 sequel.
In Happy Gilmore 2, they didn't just ignore the meme—they canonized it. Will Zalatoris actually appears in the film as a "fictionalized version of himself" who is retroactively revealed to be the grown-up version of that original kid caddy.
It’s a meta-joke that spans thirty years.
🔗 Read more: Gwendoline Butler Dead in a Row: Why This 1957 Mystery Still Packs a Punch
The New Era: Bad Bunny and the Evolution of the Bag
If you’ve watched the recent sequel on Netflix, you noticed a massive change. The happy gilmore caddy role was handed over to global superstar Bad Bunny (Benito Antonio Martínez Ocasio).
He plays Oscar Mejías, a former busboy who takes over the bag for an older, more "in pain" Happy Gilmore. It’s a huge departure from the scruffy Otto or the nervous teenager from the first film. Bad Bunny brings a different energy—sorta confused, sorta ambitious, and definitely not a golfer.
The sequel also brings back Allen Covert as Otto, proving that in the Sandler-verse, nobody ever really leaves.
What We Get Wrong About These Roles
Most people think these characters are just there for easy laughs. While that's mostly true, they serve a specific purpose in the narrative.
- The Bridge to Reality: The caddy is the only person Happy can actually talk to on the course.
- The Class Struggle: Both the original kid and Otto represent the "blue collar" world invading the "country club" world.
- The Comedic Anchor: When the golf gets too serious, the caddy is there to wash his hair in a pond or look confused about a putter.
It's easy to dismiss a role like "unnamed caddy" as a footnote. But when that footnote turns into a psychiatry professor or a multi-decade running gag with a PGA pro, you realize how much staying power these movies actually have.
If you're looking to dive deeper into the world of 90s comedy or want to see how the sequel handled these legendary characters, your best bet is to revisit the original film first. Pay attention to the background—there are more "Sandler regulars" hiding in those crowds than you'd think.
To keep up with the latest updates on the Happy Gilmore universe and other 90s nostalgia, you should follow the official social media accounts for Happy Madison Productions, as they frequently post behind-the-scenes clips of the original cast reunions.