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Entertainment

Adam Sandler’s Secret Weapon: This ‘Happy Gilmore 2’ Writer Shaped Decades of Comedy and Earned $3 Billion at the Box Office

Last updated: July 26, 2025 1:53 pm
Oliver James
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Adam Sandler’s Secret Weapon: This ‘Happy Gilmore 2’ Writer Shaped Decades of Comedy and Earned  Billion at the Box Office
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The release of “Happy Gilmore 2,” the Netflix sequel to the 1996 comedy hit, is just days away. While Hollywood hot shots might be sweating audience awareness polls or gauging social media chatter, Tim Herlihy — who co-wrote both films with star Adam Sandler — has a more pressing concern: catching up with yard work at his quiet Connecticut home.

You might not know Herlihy’s name, but you’ve laughed at his jokes. His movies with Sandler, often featuring characters in various states of arrested development, have topped $3 billion at the box office. Think classics like “Billy Madison” and “The Wedding Singer.” The pair pivoted to streaming in 2015, with Sandler’s Happy Madison Productions signing a megadeal with Netflix that’s led to such films as “The Ridiculous 6” and “Hubie Halloween.”

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“Happy Gilmore 2” is poised to be one of summer’s biggest comedies. The first film stars Sandler as a foul-tempered hockey player who invades the snobbish world of pro golf. “Happy Gilmore” was a fixture on cable, where it became quotable fodder for sports fans and millennial comedy nerds. The sequel finds Gilmore in need of a comeback, finding help along the way from pals played by Ben Stiller, Margaret Qualley and Bad Bunny.

Herlihy has co-written 13 Sandler films and executive produced several more. He says the pair click because they push to find what’s funny. Their writing process is surprisingly nuts-and-bolts, from the early development of a project (“We’re both kind of fishing around in the dark. … We take a lot of breaks because it’s hard”) to the “rapid fire” dialogue writing. The goal, ultimately, is to make each other laugh.

“There’s no such thing as perfection, so when you want to revisit something, it’s not like ‘This stinks.’ It’s ‘I know it can be better because everything can be better,’” Herlihy says. “Even the script of ‘The Godfather’ could have been even better.”

Their collaboration goes back to their days at NYU, when the roommates would kick around ideas for Sandler’s stand-up act. Though Herlihy became an accountant and an attorney, he moonlighted as a writer on “Saturday Night Live,” starting in 1994 and rising to head writer and producer by the time he left in 1999.

The duo decided to revisit “Happy Gilmore” after decades of fans clamoring for another chapter — but only if they could do something unique.

“Sometimes you see a sequel and it just feels like new characters doing the same story,” Herlihy says. “We wanted to do the opposite: our characters that we love, but a bunch of different stuff happens. They would have matured and been on the journey we all are on.”

One aspect of the movie that brings Herlihy particular pleasure is that it co-stars his son Martin Herlihy, who joined “SNL” in 2021 as a writer and cast member.

“Friends and family are packed into these movies from the get-go, and I’m glad my son now is on that list,” Herlihy says.

But even happier news? As our interview wraps, it looks like rain is on the horizon.

“I might get out of more yard work,” he says optimistically.

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