‘Happy Gilmore' is back for another round, as are Adam Sandler and his longtime collaborator

Los Angeles Times

25-07-2025

When you show up for your first day of college, you never know who your roommate will be. You could be assigned a slovenly party animal who makes your life miserable or a studious bookworm you don't see all semester.
Or maybe you share a suite with a young Adam Sandler, before either of your careers have even begun, and together you go on to create some of the most successful and enduring comedies of the last 30 years.
That is the improbable but blessedly simple origin story of Tim Herlihy, a onetime business and accounting student turned practicing lawyer, whose screenplay credits for his friend Sandler include 'Billy Madison,' about the endearing layabout; the romantic comedy 'The Wedding Singer'; and 'Happy Gilmore,' about a great (but ill-tempered) hockey player who discovers he's a great (but ill-tempered) golfer.
Over a decades-long partnership, Herlihy and Sandler have realized their achievements mostly by following wherever their own goofy muses lead them. But now they are about to try something they've almost never done: a sequel.
'Happy Gilmore 2,' which Netflix released on Friday, finds its titular bad boy well into adulthood and more mellowed out. In the star-studded follow-up — whose cast also includes Bad Bunny, Travis Kelce and Benny Safdie — Gilmore is more concerned with the needs of his family and wondering what his legacy will be.
Herlihy said the idea of a 'Happy Gilmore' sequel is one that he and Sandler resisted over the years but embraced in 'a weak moment.'
'The reason we made it is the same reason I have a dog,' Herlihy said. 'I'm like, 'No, I'm not getting a dog. No, I'm not getting a dog.' And then one day you're like, 'Well, what if I had a dog?' And then two days later, you have a dog.'
As he looks over his career, Herlihy is as surprised as anyone to find himself in a lasting and prolific creative partnership. But he is not too deeply sweating questions about why it works or what it all means.
'It's a fool's errand to try and cultivate a persona,' Herlihy said. 'At a certain point, I'm having the most fun with Adam. I'm doing the best work with Adam. I'm not making compromises with Adam.'
Herlihy, 58, who was born in Brooklyn and raised in Poughkeepsie, N.Y., spoke over lunch earlier this month at a West Village bistro not far from the New York University dormitory where he and Sandler met as freshmen in 1984.
As Herlihy recalled their fateful encounter from the day he moved into the dorm, he remembered being impressed by Sandler's apparent self-assurance. 'He seemed to know his way around, and his mother was cleaning the bathroom,' Herlihy said. 'I'm like, they put me with a sophomore?'
Sandler, in a video interview, said that Herlihy struck him as similarly confident. 'I said, 'What do you want to do?'' Sandler recalled. 'He goes, 'I think I want to be a billionaire.' Wow — OK. I didn't even think that was possible.'
They quickly bonded over their mutual love of movies like 'Caddyshack' and other shared tastes in popular culture. 'I showed up with a Police T-shirt and he had a Rodney Dangerfield T-shirt,' Sandler said. 'We were both the same size, so we traded. I said, 'Can I have that Rodney shirt?' He said, 'If you give me that Police shirt.''
More crucially, when the fledgling Sandler said he was going to start performing stand-up comedy and needed material, Herlihy used a weekend's worth of train rides to and from Poughkeepsie to scribble down some jokes for him. (Today, Herlihy claims not to remember any specific jokes. 'It wasn't the Algonquin Round Table at that point,' he said. 'It's probably even worse than you're imagining.')
In the years that followed, as Herlihy attended and graduated from NYU's law school and entered the professional world, he continued to supply Sandler with ideas and material. When Sandler landed at 'Saturday Night Live,' Herlihy helped him devise sketch characters like the slack-jawed Canteen Boy. Together, they wrote the screenplay for what became Sandler's 1995 starring vehicle 'Billy Madison,' trading pages by fax while Herlihy typed late at night on a computer at his law firm.
'Happy Gilmore,' released the following year, was started before 'Billy Madison' was released, but writing a second movie proved no easier for Herlihy and Sandler after having written their first.
'Your first movie, you put your whole heart and soul into, and every joke you ever thought of,' Herlihy explained. 'Then when you have to do another one, you're like, what are we going to do?'
Still, Herlihy, who later became an 'SNL' head writer himself, kept going from one Sandler film to the next — 'Happy Gilmore' begat 'The Wedding Singer' which begat 'The Waterboy' — until he looked up and realized he was a motion picture screenwriter.
'Around the time of 'Mr. Deeds,' we started having multiple things happening,' Herlihy said. 'I think I'm going back to the one-at-a-time thing, more out of laziness than anything else. I can only handle one at a time.'
For Herlihy, that portfolio included a sequel to 'Happy Gilmore' after the original — which was a modest $40 million hit in 1996 — went on to become a cult phenomenon.
As Christopher McDonald — who has acted in some 200 different films and TV shows but is still recognized as Happy Gilmore's malaprop-spouting nemesis, Shooter McGavin — explained, there's one reason for the film's endurance.
'Television, television, television,' McDonald said. 'It went crazy. People started watching and going, 'Oh my god, get the grandkids in here. This is sick — this is generational.' Everybody laughs, and it still holds up.'
But writing 'Happy Gilmore 2' proved as challenging as its predecessor. Herlihy and Sandler spent long days in the lobby of Sandler's production company, Happy Madison, moving index cards around a bulletin board, toying with and tossing out plot points, trying to figure out what could motivate Gilmore to pick up his clubs again at this stage of his life. (This time, he's trying to fulfill the ballet-school dreams of his daughter, played by Sandler's real-life daughter Sunny.)
The production also required Herlihy to be on set each day and come up with new lines as needed, as he did way back on the original 'Happy Gilmore.'
Julie Bowen, the 'Modern Family' star who plays Gilmore's love interest, Virginia, in both movies, recalled Herlihy as gentle and good-natured on that first film — hardly the type of guy who could have helped conceive a now-famous 'happy place' fantasy sequence that had her toting two pitchers of beer while dressed in white lingerie. 'I never felt objectified or stupid,' Bowen said of that scene. 'I felt like I was part of one of the best jokes ever.'
On 'Happy Gilmore 2,' Bowen said she saw Sandler and Herlihy working in even greater synchronicity, scouring every take and every joke to get it just right.
'If they see something not working,' she said, 'they're like, 'Give me a second,' and they'll change it. They don't think that they've written Shakespeare and you can't change a comma. It's, let's do the funniest thing that we can.'
Kyle Newacheck, who directed 'Happy Gilmore 2,' said it was both thrilling and intimidating to be working together with Sandler and Herlihy, whose name he recognized from Sandler's films and comedy albums like 'They're All Gonna Laugh at You!'
'You can tell that they go way back,' said Newacheck, who previously directed Sandler in 'Murder Mystery.' 'It's one of those relationships where somebody can move a certain way and you know that they don't particularly like that, or they have another pitch or they think they can beat it.'
Newacheck added, 'I got an incredible opportunity to sit there with, arguably, the two people that shaped my comedic membrane, and then to add what I thought could be funny. There's nothing better than saying something that makes them laugh.'
As far as Sandler is concerned, there is one straightforward reason why his partnership with Herlihy has lasted all this time: 'He's just a good, good man, funnier than everybody. I love him so much. I love every conversation with him. It's exciting to hear what his thoughts are on whatever's going on.'
Going all the way back to their first meeting, Sandler said, 'I was like, boy, this guy's quiet. He doesn't talk very much. And then throughout the year, I was like, he's funnier than everybody.'
But from Herlihy's standpoint, the collaboration thrives on contrasts between the two longtime friends. Sandler, he said, is the workaholic of the duo, working with other directors, making dramas and comedies and producing films for other writers and performers.
'The more he's doing on a movie, the more he's happy,' Herlihy said. 'I just like time off.'
Herlihy also has a unique tie back to their old stomping grounds at 'SNL': his son Martin, a member of the comedy trio Please Don't Destroy, is a writer and performer there, and they occasionally check in to share stories and advice.
When Bad Bunny, who has made multiple appearances on 'SNL,' including as host and musical guest, was being considered for a role in 'Happy Gilmore 2,' he asked Martin about him. 'He said he was really funny, but Martin never says anything bad about anybody,' Herlihy said.
(As he was happy to discover, 'Bad Bunny had tremendous capabilities that we were not aware of,' Herlihy said.)
Whether his own career is ultimately defined by his close association with Sandler, Herlihy said, will be up to history and out of his hands. But he said such distinctions were unlikely to matter in the long run, pointing to the fact that even though he's a screenwriter, he rarely remembers who wrote the movies he has seen.
'I don't know anybody who wrote the Marx Brothers movies,' he said. 'I don't know who wrote 'Kramer vs. Kramer.''
Then his mind went to an even more absurd and over-the-top scenario.
'What if you're a great movie star, you have a fantastic career, and then when you're 70 years old, you get diarrhea on Sunset Boulevard and then your obituary is 'Diarrhea Actor'?'
The bottom line, Herlihy said: 'You have no control over your obituary. Just enjoy your family and have some laughs.'