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There’s an old maxim that Hollywood stars like to bandy around: one for them, one for me. Usually what that means is that they’ll try to do a blockbuster movie, working for the studios; and then they do a smaller, more personal film; balancing expanding their star appeal with stretching themselves as actors. But without making too broad a generalization, often careers for top-tier stars have a way of becoming one for them, another for them, rather than finding that balance.

And then there’s Adam Sandler. Love him, hate him, or somewhere in between, the 58-year-old star has managed to build his career to a place where they’re all for 'me.' Whether he’s doing comedy, drama, or something entirely new, Sandler is a singular creator who serves his muse in every project he does.

This dichotomy is likely top of mind for a lot of fans – and detractors – as Happy Gilmore 2, the belated sequel to 1996 hit comedy Happy Gilmore, drops a hole-in-one on Netflix this month. Normally this sort of thing seems like a cash-grab, something that a fading star does to recapture some of their old glory. For Sandler, though, making Happy Gilmore 2 good is as important to him as any other project he participates in. And maybe even more so.

Adam Sandler doesn't want to let fans down

"People have been asking me for a long time, ‘Do Happy Gilmore 2,’ and I was always like, 'Nah, I'll only let you down,'" Sandler told Jimmy Fallon on The Tonight Show in 2024. "But then me and my buddy, Tim Herlihy, we came up with this idea. We're really excited about it. We wrote our asses off. We're continuing to try to make it a movie that you guys will like."

Even with the care Sandler expressed on Fallon’s show, it’s easy to use Sandler as a punching bag. His career contains a string of crowd-pleasing hits that often rely on cheap, broad humor to appeal to the widest masses possible. But that was readily apparent since the moment he first got hired by Saturday Night Live in 1990, and it’s something that’s stayed consistent, 35 years later. In fact, Sandler’s Netflix era, which began in 2016 freed the comedian from the hegemony of the box office, and let him and his friends do pretty much whatever they wanted.

That’s included broad character plays like Hubie Halloween, the Murder Mystery movies with Jennifer Aniston, and very likely Happy Gilmore 2. But it’s also led to more interesting movies like the coming of age drama You Are So Not Invited to My Bat Mitzvah, or the sci-fi movie Spaceman.

Adam Sandler does movies on his terms (and for his family vacations)

Do some of those broad comedies seem like Sandler is just doing them for a free vacation with his friends? Well… Yes. Sandler has been pretty open about that since 2014, when he said as much on Jimmy Kimmel Live.

“Yes,” said Sandler via The AV Club, when asked if he chooses vacation locations for his movies, and his movies based on vacation locations. “I have done that since 50 First Dates. It was written in another place. I said, ‘Imagine if we did it in Hawaii, how great that movie would be.’ And they said, ‘Yeah, that’s a very artistic idea.’ I’ve been doing that ever since.”

Look, not to read too much into an 11-year-old statement on a comedy talk show, but note that Sandler does say it was a “very artistic idea.” When it comes to 50 First Dates, which was originally titled Fifty First Kisses until the studio changed it, Sandler significantly reworked the script, including shifting the locale from Seattle to Hawaii. Nothing against the Emerald City, but moving from a place where it rains all the time to where the sun shines constantly is a clear, yes, artistic choice about how to frame your comedy.

Adam Sandler isn't afraid to be afraid

And that’s panned out in some of Sandler’s more surprising choices. In 2002, he appeared in Paul Thomas Anderson’s Punch-Drunk Love, a starring role that brought concerned and confused reactions from fans of the auteur director. Yet Sandler was roundly praised for the role, though it was a box-office bomb. There was a long gap of broad (yet successful) comedies like the Grown Ups franchise or the kid movie behemoth Hotel Transylvania after that, but he’s also peppered more dramatic roles here and there, with mixed results. Reign Over Me in 2007, The Meyerowitz Stories in 2017.

But when he teamed up with the Safdie Brothers for Uncut Gems in 2019 (the same year as the first Murder Mystery), he was again roundly praised. Though his Academy Award aspirations didn’t pan out, neither did Sandler’s threat to “come back and do one again that is so bad on purpose just to make you all pay” if he didn’t win an Oscar.

In fact, since then, he’s more frequently experimented with how he executes his comedy. That includes 2022’s Hustle, a basketball drama that felt like Sandler experimenting in the same realm as Uncut Gems, and even last year’s Benny Safdie-directed Netflix stand-up special, Adam Sandler: Love You.

The thing is, despite breaking onto the scene with big characters like Opera Man on SNL, mixing drama and comedy have always been part of the plan for Sandler.

“I’ve done both for a long time,” Sandler told AARP, via CinemaBlend, back in 2022. “When I went to NYU, I did a lot of scenes that were just dramatic, not funny. Punch-Drunk Love was 20 years ago. That was different and exciting. I like giving myself over to a new challenge. Sometimes I feel like I’m tapped out with new thoughts, and then all of a sudden, something new comes up and I go, ‘OK, how can I make this happen?’ It was cool as hell pushing myself in new ways like I did on Uncut Gems. Running around the Diamond District in New York, the intensity of that amazing character, or in Hustle, being around the greatest NBA players and not worrying about laughs as much as what each character is going through and pulling for. But I do love comedy more than anything.”

To wrap things back around to Happy Gilmore 2, even with the clear nostalgia play of that movie, Sandler is still doing things his own way. In November, he’s co-starring with George Clooney in Noah Baumbach’s dramedy Jay Kelly. And while not much has been announced in Sandler’s future other than a prodigious amount of producing projects through his company, Happy Madison (named for two of his most famous film creations), he’s planning on reteaming with the Safdie Brothers for a spiritual sequel to Uncut Gems set in the world of baseball.

Until that happens, though, expect to see more broad comedies, plenty of weird experiments, and likely a film that is essentially just there so he can go on vacation with friends. Sandler refuses to be pinned down, and even while he delivers what Netflix – and the audience – wants, he is still clearly following wherever his muse takes him. It’s all for him, not them, and we’re just along for the ride.

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