The journey from a shaggy-haired college kid to starring alongside Happy Gilmore 2

It’s 2015, and Will Zalatoris has just captured the Genesis Invitational Collegiate Showcase. The problem? Like most college students, he hadn’t visited a barber in roughly six months. The Golf Channel posted his victory photo, and within hours, the internet had made its verdict: this blonde, lanky kid was the spitting image of Happy Gilmore’s caddie from the 1996 comedy classic.

The comparison stuck. What began as a casual observation from golf fans quickly snowballed into a decade-long phenomenon that would define Zalatoris’s public persona. “I won the Collegiate Showcase in 2015 at the now-Genesis Invitational, and I had, typical college kid, hadn’t gotten a haircut in about five or six months,” Zalatoris recently explained at the Valspar Championship. “Golf Channel posted a photo after I won the Showcase, and somebody mentioned it and immediately it picked up.”

The 2021 Masters: When Happy Gilmore Himself Took Notice

By 2021, Zalatoris had worked his way to Augusta National for his Masters debut. Still grinding on the Korn Ferry Tour, he found himself in contention on golf’s biggest stage. The Happy Gilmore comparisons reached a crescendo on social media, attracting attention from an unexpected source.

Adam Sandler himself entered the conversation. “Have fun today young man. Mr. Gilmore is watching you and very proud,” Sandler tweeted before Zalatoris’s final round. The moment marked a surreal intersection of sports and entertainment – the actual Happy Gilmore was cheering on his fictional caddie’s real-life doppelganger.

Zalatoris finished runner-up that Sunday, marking his first of three major championship second-place finishes. The performance announced his arrival on golf’s biggest stage while cementing the Happy Gilmore connection that had followed him from his college days.

Embracing the Comparison: The Wedge That Made Headlines

Rather than shy away from the constant comparisons, Zalatoris leaned into the moment. He commissioned a custom stamp for his lob wedge featuring the iconic line: “Mr. Gilmore I’m your caddy.” The move demonstrated his willingness to embrace the humor while adding personality to professional golf.

The wedge became a symbol of Zalatoris’s approach to his unexpected fame. Instead of treating the comparison as a distraction, he turned it into an asset, connecting with fans who appreciated his self-awareness and good humor about the situation.

Full Circle: Happy Gilmore 2 and “Gilmore’s Caddie”

The story reaches its peak in 2025 with Zalatoris set to appear in Happy Gilmore 2, premiering July 25th on Netflix. At this year’s Valspar Championship, where players could customize their caddie bibs, Zalatoris chose “Gilmore’s Caddie” – a decision that received Adam Sandler’s seal of approval.

“I had a good giggle when they asked me what I wanted to put on the back of my caddie bib and I sent it to Adam and he loved it,” Zalatoris said. The filming experience proved as entertaining as expected from a Sandler production. “Basically they said, ‘Act like a moron as much as you possibly can,’ and I said, ‘Well, that’s pretty easy for me,'” he joked.

Zalatoris joins fellow tour professionals Scottie Scheffler, Justin Thomas, Rory McIlroy, and Keegan Bradley in the sequel’s cast, though none share his unique connection to the original film.

The Bigger Picture: More Than Just a Resemblance

Zalatoris’s embrace of the Happy Gilmore comparison reflects broader changes in how professional athletes connect with audiences. His willingness to participate in the humor has helped bridge the gap between golf’s traditional formality and modern fan engagement.

The progression from college unknown to major contender to movie star demonstrates how authenticity resonates in today’s sports landscape. Zalatoris has built genuine connections with fans through self-deprecating humor rather than manufactured persona.

A Hollywood Ending Still Being Written

Ten years after that fateful haircut launched a thousand memes, Will Zalatoris has established himself as both a legitimate PGA Tour contender and an unexpected entertainment figure. His journey from accidental doppelganger to Happy Gilmore 2 cast member represents one of golf’s most unique career arcs.

The story continues to evolve, with Zalatoris proving that sometimes embracing life’s absurdities leads to opportunities nobody could have scripted. From shaggy-haired college champion to Netflix movie star, his path shows that in professional golf – and life – the best approach is often simply to enjoy the ride.