Happy Gilmore 2 (2025) Review - A Happily Successful Legacy Sequel

2025 marks the 30th anniversary of Billy Madison (1995); the film I consider the genesis of the 'Sandler comedy' - comedies starring (although not required) Adam Sandler in the roles of essentially man children best identified by their temper, stupidity and horniness. While an oversimplification I find these three traits to be applicable to nearly every Sandler performance up to around the late 2000s. It's ironically the least traditional Sandler film of this era, Paul Thomas Anderson's masterful Punch-Drunk Love (2002) that best deconstructs the traits what make a Sandler comedy a Sandler comedy, not from a place of malice but rather as a fan of comedy.

I find it hard to talk about Sandler comedies, since I feel perspectives like PTA's and my own form a minority within the binary of you either love the Sandman or think he's the comedy equivalent of you having a bath with the toaster. Yes, a critical reappraisal of his comedies expose a pattern of damaging stereotypes with perhaps most clearly what we may now call a streak of toxic masculinity, championing the male gaze and flourishing in frat-boy behaviour, something I am not here to justify, but what I think these films demonstrate is a consistent subtext - one of male fragility and struggles to assert worth within the turn of the millennium. This is certainly a stretch, believe me I am not suggesting these were the explicit messages intended, but within Punch-Drunk Love's juxtaposing of the Sandler comedy formula of a bumbling angered oaf searching for love against an images of male heterosexual and fiscal inadequacy I think PTA saw in Sandler's rage a darker anxiety heightened for comedic effort.

Psychoanalysis of Sandler comedies is a niche interest of mine, sparked by a university assignment I wrote, hence my choice to preface my thoughts on Happy Gilmore 2 (2025) with a brief dive. In truth, I'm a fan of Adam Sandler both in my post-ironic thematic analysis of his films but also simply as a fan of comedy. While many miss the mark and rightfully are criticised for their problematic representation and hack humour, there's a blue-collar philosophy to Sandler's ethic and films I respect. While I love arthouse films and such, I think there's a need for comedies just for the sake of comedy; to appeal to our own personal situations and bring some brevity which even though undeniably androcentric here is still a relief millions want and one Sandler often delivers. Whether or not I think his films land varies and I understand why critical circles scoff at any further examination of his career, however he is comfortable fulfilling a role in the industry not many are, a fact I think is neither inherently wrong.

I think its important to appreciate the albeit limited dimensions to Sandler's characters as Happy Gilmore 2 reads as a swansong to this archetype. The film follows an unhappily retired Happy pushing 60 forced back into golf in order to raise the money for his daughter's ballet school fees. It's a premise reminiscent of the original Happy Gilmore's (1996) about raising enough money to save his grandmother's house but this isn't the same energetic Happy as before. To continue my self proclaimed title of a Sandler scholar, I like to divide his career into three eras distinguished by the overarching traits of his characters, tones, method of distribution and legacy of the films themselves; we have the The Early Years (1995 - 2003), the Family Years (2004 - 2015) and the Netflix years (2016 - Present). The Early Years are the prime era for how audiences remember Sandler as a performer; in films like The Waterboy (1998) or Little Nicky (2000) he is at his most extreme - delivering excessive slapstick, mugging and that voice. You know the one.

The Family Years marked a gradual departure from the overt obnoxious projections of young masculinity and into more of a schlubby hopeless romantic with a milder anger streak - marked also by more appearances in family orientated outings like Bedtime Stories (2008) and Hotel Transylvania (2012). Sandler definitely starred in numerous adult comedies during this time but the vibe had shifted, he was no longer a hip young comedian and the poor reviews only grew worse. It's evident that Sandler's priorities shifted when he had children, those days as the Bad Boys of SNL couldn't last forever and even if Sandler's comedic chops didn't change too much there was just no way an older man in the 2010s could have the energy or dignity to continue such aggressive roles.

That leads us to the Netflix years. Sandler wasn't the box office draw he once was and neither were comedies (here's to hoping The Naked Gun (2025) reboot can be a trendsetter) so the star and his cohort found a new home in Netflix. These years haven't fared much better for the actor's comedies although his Independent Spirit Award for Best Male Lead in the crime-drama Uncut Gems (2019) has to be mentioned. I think this era is best viewed as a winding down for Sandler, he's still out making comedies but with the more targeted nature of streaming its now mostly his fans checking out the latest projects. With Happy Gilmore 2 we see the culmination of this evolution.

Sandler plays a drunk beaten-down Happy here. The comedy isn't derived from watching this sexed-up mentally deranged fish out of water find his place in the world of golf but rather from the satisfaction of watching this older-fashioned past his prime father reclaim his autonomy in a culture that has moved on from him. Rather commendably, Sandler isn't trying to act like he's in his twenties again as we all know that just doesn't work given his aforementioned growth away from the original iteration of the Sandler persona. Believe me, we aren't seeing some new side to his range like in Uncut Gems or masterful inversion like Punch-Drunk Love, it's just the purest distillation of modern Sandler versus the the purest distillation of classic Sandler.

Unplanned Sonic Generations analogies aside, this is a nice junction into discussing how the film stands as a legacy sequel to the original and I am happy to report the film surpassed my expectations. I'm pretty jaded to legacy sequels, while every once in a blue moon we get treated to a Blade Runner 2049 (2017) more often than not we get a Ghostbusters: Afterlife (2021); boomers clinging on to any vestige of nostalgia they can as we are destined to an eternity of 80s reboots and landfills of Funko pops. Happy Gilmore 2 is very aware that its a sequel but doesn't fall into many of common traps.

The film definitely harvests a majority of its jokes from the original through callbacks and these tread the fine line well between being lazy and fresh. The wheel isn't being reinvented but there's a clear effort to update the jokes in line with the current Sandler stardom. Returning characters outside of Sandler like Christopher McDonald's Shooter McGavin and Ben Stiller's Hal L. while inarguably dependent on familiarity with the original (a problem I will delve into later) are given fresh twists that perfectly compliment the idea of Happy Gilmore 2 as a bookend to Sandler's older works. New characters like Lavell Crawford as Slim Peterson, Bad Bunny as Oscar and John Daly as, well John Daly, effortlessly slip into the familiar world and provide some fresh material beyond the reference humour.

Even though I enjoy Happy Gilmore 2 for how playful it gets with the 1996 classic, the needless flashbacks got tiresome especially with its almost two hour length. Let's be honest here, its a Netflix sequel releasing in competition with the busiest blockbuster month of the year the vast majority watching this film are familiar with the original. It felt like the film had to pause every ten minutes to just play a YouTube compilation of Happy Gilmore's funniest moments completely breaking the otherwise adequate pace of the film. The tonal whiplash between Happy's alcoholism with the typical Sandler zany world was also a bit distracting; these scenes may best encapsulate my interest in the film's commentary on the character and by extension Sandler's legacy but I couldn't help but laugh at these parts not due to Sandler's acting but rather the sheer disconnect between this sincerity and whatever antics were juxtaposed.

I also wish Benny Safdie's antagonistic Frank Manatee got more to do. The actor delivers a strong image with what he has but it feels he gets lost in the chaos and fails to reach the greatness of Shooter McGavin. Hell, if anything Hal L. feels like more of an antagonist at points.

So what does this all mean? Happy Gilmore 2 definitely won't be Sandler's final outing, despite all my focus on how it could very well be. The truth is a lot of what I've said is me understanding my relationship with Sandler's works; the good, the bad and the questionable. For most people, Happy Gilmore 2 will just be another Adam Sandler movie that gives a dose of nostalgia which I think is an appropriate legacy. The majority of my analysis is based off the dialogues between subtexts, at its core what we have here is a comedy not trying to set the world aflame or reach cult status like the first but rather provide comforting entertainment for its audiences. Happy Gilmore 2 is simply another Happy Madison production and that's all you'll need to know to decide whether or not the film will work for you.

3/5