There was a time when it was easy to answer the question: What is your favorite movie? I was a child, or maybe a teenager, then, with a fairly regimented taste in American comedies that aligned with popular sensibilities. Many in that pyramid were alumni from Saturday Night Live, but somewhere near the top, just a bit above Will Ferrell, was Adam Sandler. During that time, it was easy to notice the generational divides on who loved and loathed his style of humor, which often leaned into the juvenile as he mixed physical comedy with subtler shades of buffoonery. Nonetheless, there were a handful of films that have come to define his career. He will always be beloved for a handful of reasons, but none more than Happy Gilmore (1996).
More often than not, if someone I know goes to a putting course, they will feel the urge to quote the hockey player-turned-golfer by yelling at their ball and imitating one of his many erratic swings. We’re not the type to necessarily watch golf (not unless it’s Holey Moley, anyway), but there is something essential about watching Sandler get beaten up by Bob Barker and riding your club like a bull. It’s one of those increasingly rare films that has transcended the celluloid it was produced on and has become a language that I’ve heard everywhere from high school classrooms to coworkers passing long hours at a grocery store. Even if Sandler’s breakout hits are now few and far between, Happy Gilmore has built so much good will that it can’t help but produce a built-in nostalgia for those old enough to rewatch the DVD until the scratches overpowered the playback.
On Friday, the arguable king of sports comedy in the subdivision of golf will be getting a sequel called Happy Gilmore 2 (2025). The long answer is that sequels are rarely as good as their originals. Given that it is nearly a half-hour longer and has a prominent cameo line-up already listed on Wikipedia, it feels like an awful lot of padding that is more in line with latter-day Sandler flicks. The only real upside is that director Kyle Newacheck made one of Sandman’s better contemporary titles with Murder Mystery (2019), and that Sandler has made a comfortable groove with ensemble titles like Funny People (2009). Even the prominent billing of family suggests that this is as much a comedy as it is yet another one of his heartfelt legacy tales that have made him a welcome addition to the goofy dad genre.
If you want a much shorter answer… I just love Happy Gilmore.
For months now, I have seen those promos and have tapped into a sensibility not dissimilar from my middle school days, where I’d see commercials for his latest and start planning my Friday. I would be there in a crowded theater with everybody laughing. I’m unsure if this is vintage Sandler or just a cynical cash grab, but in my head I’m already smiling at the emergence of Shooter McGavin and the potential for scenes on par with the first. It is doubtful. As someone who has grown up in an age defined largely by franchises, Happy Gilmore 2 doesn’t live among a promising circle. Still… I watched that Sandler and Barker reunion from years back and felt the warm fuzzies. I still tune in for 20 minutes whenever I find it and just laugh.
At some point, your favorite movie transcends typical classification. It becomes tied to a time and place in such a way that you begin to recall the sleepovers and schoolyard conversations where you found people who shared your passion. It’s a work that unites the larger culture, and as a preteen sometime in the early 2000s (maybe even late 90s), I sat at my aunt’s house as she slid in the VHS tape and introduced me to the world of Happy Gilmore and the greater cult of personality that remains Adam Sandler.
Maybe I love Happy Gilmore the most because it was the gateway. It was the moment when I discovered a world of comedy that felt new and radical. Sandler had this knack for digging into an unbridled id while capturing an incredible mix of humanity with slapstick comedy. You loved him because his motivations came from someplace recognizable. He wanted to do right by his grandma and reflected a working-class individual who had failed to find direction in life. His dream of being a hockey player was largely a failure, and he had to settle for a career that was, in polite terms, square.
Sandler was the poster child for Saturday Night Live’s 1990s roster of rock star comedians. Days before releasing this comedy, he came out with his music and sketch comedy album “What the Hell Happened to Me?” He was very much a Gen-X archetype who rebelled against the conformity around him by introducing crass and vulgar tactics into the mainstream. In theory, it was a more palatable version of John Waters’ 80s films.
Even as he remained poison for critics, the reason he has transcended the test of time while other nose-flicking 90s talents have disappeared may just be that he was first and foremost about humanity. There were gross-out gags and moments that are pure bafflement, but the arc of Happy Gilmore ultimately is a classic underdog story where a goodhearted man overcomes his flaws to save the day. It does help that I find the writing to be sharp and the ensemble is delightful even in short clips. Who could forget Richard Kiel bending a golf club? Or Alan Covert going from homeless to caddy? Or Joe Flaherty just yelling “You will not make this putt, you jackass” at inappropriate times? Or the unfortunate timing of a certain air conditioner?
Many Sandler films fall under the “acquired taste” banner. I’d argue his preceding film, Billy Madison (1995), is even more of a cult film than this. Whereas that film played into arrested development, Happy Gilmore was a fractured version of the American Dream as reenvisioned for Gen-X. As the world threatened to take away everything that Happy held dear, he had to enter the workforce and struggle for what mattered most. In the process, there’s meta humor about selling out and the societal divides between upper-class snobbery and Happy’s casual frankness. He’s not the first to walk into a room and shock the monocle crowd, but he’s among the most enjoyable simply because there’s some part of him that clearly wants to be accepted by them.
And ye, he has one amazing character flaw. He has the swing to end all swings. He does a better job of attracting the youth market than Caitlin Clark. And yet, because he’s a male and this is the late-90s, he has rage issues that haven’t been fully processed. He’s like The Incredible Hulk turning to Chubbs (Carl Weathers) as a form of counseling as he tries to keep everything together, not only for himself, but for his grandmother. This is a story about a man searching beyond his own selfishness. He must become his best self before it’s too late.
The only issue is that Sandler is a master at the freakout. Golf is objectively a patient sport. Through the 18 holes, a player must be willing to deal with a lot of downtime. The constant variables playing against an easy hole-in-one can frustrate those without discipline to just take the loss. Happy is one of those people and, in one of the greatest scenes in 1990s comedy, he attempts to tap a ball into a hole before having a mental breakdown that involves: yelling at the ball, throwing his club, and beating up spectators. The pathos behind this aggression works both as comedy but also as a hurdle for Gen-X to evolve into the competent leaders they should be.
I’d argue that the film works because it knows where the boundaries are. This may be ribald comedy at its core, but the cruelty is never overbearing. There may be a lot of animosity and scenes more fitting for a wrestling match, but it all exists within a framework of perfect contrast. What happens when you mix the settled manner of golf with a man who once took off his ice skates to beat up somebody? The challenge of making that man likable is difficult, but director Dennis Dugan does a fantastic job of making him a recognizable archetype, in some ways no different than Rocky Balboa. Still, this is Sandler finally coming into his own as a lead actor. This is where his goofy grin and silly voices feel like they serve more than a surface-level sketch. Even if he’s still at odds with the larger public discourse, he has become the cool bad boy, and I think Happy Gilmore works largely because you can feel that animosity translate to the tone in ways that necessarily wouldn’t a decade later.
It would be easy to run down everything I love about this film, though it would also be easier to just command you to watch it. Even as I’ve gone through highs and lows with Sandler’s career, there hasn’t been a time when I disliked Happy Gilmore. He’s maybe strayed too far into lazy practices here or there, but the essence of why Sandler will always matter to me is found in those 90 minutes. The comedy lands. Even if many moments are closer to quick gags, I commend how much they reinvent golf into a modern world of slapstick. It’s absurd and sometimes confusing, but that’s how the sport has always looked to an outsider. Happy Gilmore works because even as it “destroys” everything, there is some sense that Happy wants to master and even respect it. This ends with a collective cheer where the good guys win and, as the sequel suggests, inspires a new base to tune in.
Part of me wonders if Happy Gilmore 2 could capture any of that same charm. I’ve long felt that one of the downsides of later Sandler is that he’s lost some of that underdog appeal. He’s found other ways to channel his humor, but will a character so defined by aggression work in a time where Sandler is more defined as a humble father type? In fairness, I don’t want some great psych evaluation of who Happy is. To me, that’s one of the joys of 90s comedies that more self-aware contemporaries lack. I just want to spend two hours with him and see what he’s up to. Maybe it won’t be as good. Maybe I’ll never watch it again.
Even then, I see Sandler in that jersey on the poster and I get hyped all over again. I’m not sure that I’ve been this thrilled since Uncut Gems (2019) to see what he’s been up to. Who knows. Maybe I’m just caught up in the franchise machine and will be dealt the same lousy hand a lot of these sequels have given. I doubt it in part because I have liked a lot of modern Sandler. His recent stand-up special is one of his greatest works to date. Only time will tell if this will make me clamor for a trilogy, or if it’ll just give me an excuse to rewatch one of my all-time favorites. No matter what, I’ll be having a good time watching golf this weekend.
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