‘Happy Gilmore 2’ review: A haphazard return

Adam Sandler tees off again in Happy Gilmore 2, which is neither a whiff nor a hole-in-one for the aging comedy superstar.

There’s something strange about Happy Gilmore 2. This is a decades-later sequel to Adam Sandler’s classic 1996 sports comedy, which itself was the second in a one-two punch of flicks that kicked-off his film career after 1995’s Billy Madison. It’s also the latest feature in what is seemingly Sandler’s endless relationship with Netflix that dates back to 2014. Yet somehow, the comedian’s much-anticipated (and much-feared) follow-up is the rare Sandler farce that’s arrived with high expectations.

Sandler’s comfortably unfussy and free-spirited form of comedy can often result in lackluster (or simply awful) additions to his expansive filmography. Sure, he takes breaks by proving himself as an unlikely dramatic thespian for the likes of Paul Thomas Anderson, Noah Baumbach, and the Safdie brothers. But this is a return to one of Sandler’s golden geese. This is Sandler bringing back one of his most valued, career-defining characters. Would it stand up to what he did in his versatile youth? Or will it showcase how much the comic can swing and miss?

The answer, expectedly, falls somewhere in the middle of the course. It’s often exactly the sort of indolent, underwhelming cash-in that these long-overdue sequels tend to be: overstuffed with noxious celebrity cameos, an overworked oldies soundtrack, and tiresome flashbacks to the original. But it’s also a somber, heartfelt exploration of aging, dying, lost youth, and the desire to make the best life for one’s loved ones when life has you over par. There aren’t any particularly novel or unique insights, but it’s also a more intriguingly personal project for Sandler than his fans might anticipate. The Sandman will always do whatever he wants to do, and more often than not, the result is something less than desirable. But Happy Gilmore 2 is somehow both trite and tender, and also pretty darn funny in some places.

The Gilmore gang.

Happy Gilmore 2 is at its best by starting bleak as hell. Following win and win, Gilmore suffers loss after loss. Tragedy befalls his family of five kids and alcoholism causes the one-time athlete to lose everything, including his grandma’s home. Destitute and devastated, Gilmore is trying to make it by with his exceptionally supportive kids, including his youngest child/dance protégé daughter Vienna (Sunny Sandler, the actor’s actual daughter). She has what it takes to make it at an international ballet school, but those institutions aren’t cheap. Gilmore needs a lot of cash if he wants the best for his little girl, and there’s only one way he can make that money. The problem is that he hasn’t picked up his clubs in a decade and he doesn’t know if he has what it takes in a young man’s game.

From there, we’re introduced to an assortment of new characters. The most notable is Benny Safdie’s villainous Frank Manatee, the CEO of Maxi Energy Drink who sets out to make a new, extreme form of professional golf. There’s also a slew of broad-reaching cameos that are there seemingly to make the random person turn their attention away from their phone, laundry, or what-have-you and back to the movie at hand. Happy Gilmore 2 will also make time and effort to bring back as many characters from the original as they can (including some who’ve passed away) even if it means bringing the movie to a halt. Like many nostalgic decades-after sequels, Happy Gilmore 2 can feel less like a proper continuation and more like an expensive reunion tour.

These are certainly the gaudier aspects of Happy Gilmore 2. Director Kyle Newacheck (Murder Mystery) all-too-often favors an over-saturated, overly-glossy presentation that makes the movie look and feel like a tedious Super Bowl commercial. It’s not often that one longs for the more subdued filmmaking styles of Sandler’s older films, but that’s what this prolonged sequel’s waxy-looking Netflix sheen can do at times. When it comes to these decades later sequels to ‘90s comedies (Good Burger 2, Dumb and Dumber To, Clerks III), there’s the sad expectation that digital photography makes everyone look older and more gray than they already are, bringing an extra layer of sadness to this seemingly unnecessary affair.

Sad Gilmore.

To its credit, Happy Gilmore 2 leans into this aching sadness in the first half, which makes it clear that screenwriters Sandler and Tim Herlihy (who also wrote the original) have a bit more on their minds here than a simple Netflix cash-in. Many members of the original cast and some of Sandler’s former Saturday Night Live buddies have passed away. Rather than simply working around these misfortunes, Sandler and Herlihy lean into the sorrow of it all, while not letting it take away from the intrinsic comedy. The cause of poor Gilmore’s greatest sorrow is the source of one of the movie’s biggest laughs. Likewise, the sequel finds unlikely mileage from Gilmore’s rampant alcoholism, going to likably bizarre lengths to show how much he’ll hide his booze in miscellaneous work/household items.

Had the movie stayed on this darkly humorous wavelength, owning up to the inherent misery of seeing a character we love out of his prime and out of his element again for fame and fortune would’ve been bold. It may not have won over all the diehards, but it would’ve had a hearty fan amongst those still rooting for Sandler to turn over a new leaf. Alas, it’s only a matter of time until the mechanics of these widely appealing studio sequels angrily strike in, which make the movie less appealing. Are the folks who get a kick out of seeing TikTok star Alix Earle also laughing when beloved character actor Steve Buscemi is pissing in a mailbox? Does wrestler Nikki Bella only appear in Happy Gilmore 2 if they forcibly shoe-horn in a cameo from Jeopardy’s Ken Jennings?

Not quite on par, but still in the hole.

By bloating the runtime and spending a fair amount of it thinking about death and the inevitable passing of time, it was always an uphill battle for Happy Gilmore 2 to reach the delirious heights of the original charmer. The lack of the late great Carl Weathers is certainly felt here. But, in total fairness, I doubt many of the people involved or watching at home expected something on par with what they had with the first film.

One could argue that, outside of his prestige pictures, Happy Gilmore is Sandler’s finest feature. Furthermore, nobody would expect Sandler and crew to hit the same level as he did in his youth. One thing that always seems to sink these later sequels is that the people involved just aren’t the same people they were decades years ago. Bill and Ted can face the music, but they can’t be the same lunkheads that they were in their time-traveling years without it being pretty sad. Sandler, like Gilmore, isn’t the same loose cannon who came in with bold indignation and shook up the game in the process. But it’s an immense credit to Sandler’s highly affable screen presence that he can try to split the difference between boyish glee and mature reflection and kinda, sorta, just barely, pull it off — at least enough to put the ball inside the hole.

What truly works in Happy Gilmore 2’s favor is that, unlike several of the misfortune sequels mentioned above, Newacheck’s sequel knows how to surprise. Some celebrity cameos seem like throwaway gags, including elderly golf legend John Daly and music superstar Bad Bunny, only to flesh out into modest supporting turns where both non-actors outshine a few of the credible comedians on hand. Likewise, returning supporting players like Christopher McDonald as Shooter McGavin initially feel forced, but each performer is so clearly game to reprise these famous roles that they make every little bit of screen time count. That’s most especially the case for McDonald, who is relishing the chance to reprise the role that’ll live on as the one that he’s most remembered for.

The bottom line.

Many viewers will be quick to deem Happy Gilmore 2 the inferior sequel that it is. To be fair, it is symptomatic of everything that is tiresome and infuriating about these sorts of ventures. But maybe I’m just a sucker for a good comeback story, or maybe I’m just happy to see Happy Gilmore do his thing again. Happy Gilmore 2, for all its faults, still proves to be a generally likable and vaguely moving effort, one that showcases that Sandler knows how to get a birdie, even when the odds are against him and everyone is expecting him to lose. There’s a time when critics and audiences would instantly write off Happy Gilmore 2, sight unseen. That we take this boyish sports lark even a little seriously proves that Sandler won in the long game.

Happy Gilmore 2 is streaming exclusively on Netflix. Watch the trailer here.

Images courtesy of Netflix. Read more articles by Will Ashton here.