Lasciate ogne speranza, voi chi’intrate. How did it come to this? At the height of his power in Hollywood in 1999, Adam Sandler founded his own production company as a way to continue making the movies he enjoys. Over the years his films have slowly morphed into a pariah on the landscape of big budget studio comedies, becoming thinly veiled excuses for lavish vacations. But do they truly represent the nadir in the career of one of comedy’s once-brightest stars? Are there any hidden or underrated gems? Is there such a thing as too few fart jokes? Will I retain any sense of sanity by the end of this? Join me and find out, as we venture to the Happy Valley.

By nearly every metric, I should probably hate Hubie Halloween a lot more than I actually do. But somewhere along the way, I shed my pretension and found myself simply letting the film wash over me, even laughing at times! Though what I found most fascinating about the film wasn’t the screenplay (by Tim Herlihy and Adam Sandler), the jokes, the performances, the direction (Steve Brill) or even the cinematography (Seamus Tierney), but rather how the film feels like a kind of demarcation point and, strangely, a kind of love letter to Sandler.

For as formulaic as the Happy Madison films have been — and this one is certainly not immune to that label — the high-minded concept behind Hubie Halloween at least managed to keep me intrigued from scene to scene. It may be surprising to the casual viewer, but the well of Halloween films (not including outright horror movies) throughout Hollywood history runs almost as deep as the Christmas film. What’s most surprising about Hubie Halloween is how it approaches the holiday from such an original angle. Sandler stars as the titular Hubie Dubois, who lives in the town of Salem, Massachusetts, and has always approached Halloween as a sort of guardian, ensuring that everyone has a safe, enjoyable evening.

Naturally, the townspeople resent him for his wet-blanket tendencies toward any shenanigans, but the film goes out of its way to convince us that it’s worth rooting for Hubie. Add on subplots that involve a romance with Violet Valentine (Julie Bowen, back again from Happy Gilmore), a similar romance between her son Tommy (Noah Schnapp) and Megan (Paris Berelc), the mystery of the adult townspeople who torment Hubie and begin to disappear, and an escapee from the nearby mental institution, and it almost begins to feel like too many pumpkins are in the patch. But at some point, I began to view the premise of the film as simply a vehicle for Sandler to have episodic misadventures around the town and all the weirdos that inhabit it. Hubie may be the butt of the joke around town, but it never feels like the film is mean-spirited in the way that past entries (looking at you, Bucky) have felt.

We’ve covered a handful of Sandler films where he takes the backseat to let his friends loose and steal the scene, and Hubie Halloween may very well be the best of them. Steve Buscemi, as gifted as he can be, often gets relegated to one-note characters, but here he seems to genuinely grip the weirdness of his character’s foundation. And how refreshing is it to finally see Shaquille O’Neal utilized correctly, by playing off our pre-conceived notions beyond “Check out how tall this guy is!” His scene may have been my favorite of the entire film, especially when it goes a step further and fully embraces its bonkers potential.

Would I feel as rosy about the film if it wasn’t the last one in this series? Maybe not, but the highs are fairly high and the lows are relatively low. Yes, this is a film where June Squibb’s entire wardrobe essentially exists as its own punchline, but somehow it’s not a harbinger of Hubie Halloween’s doom. Though there is plenty of potty humor throughout the film, it’s certainly not as outlandish or tacked-on as Sandler’s worst. And the colorful holiday setting actually manages to make the film memorable, as opposed to previous vacation-based locales.

What sets Hubie apart most, and what I was most interested in, is the way it harkens back to Sandler’s earlier career and what it has to say about his current status. Of course, Sandler has thrown in references to past films throughout his Happy Madison days, but here it’s right in the open. Indeed, the opening scene features Ben Stiller’s instantly recognizable nurse from Happy Gilmore. Not to mention Julie Bowen’s involvement, her character’s name (every one of Sandler’s love interests in his early films had the initials “V.V.”), and the surname of the town bullies (O’Doyle). Perhaps it’s a bit of a stretch, but Hubie Halloween can almost be read as a meta-argument for Sandler’s continued existence amongst the modern comedy landscape.

The film is almost a character study of Hubie who, much like Billy Madison or Bobby Boucher, is an overly earnest man in a cynical world constantly working to bring him down. Sandler, perhaps more than any other comedian or actor, has had a career as fascinating as it is confounding. Debates continue to rage on around not only his films but his intent behind them: How much effort does he actively put into every role, and how disappointed do we have a right to be when he doesn’t live up to our expectations? For once, I felt an understanding for Sandler as a bastion of an almost-bygone era, clinging on for dear life to the brand of comedy he and his friends enjoy the most. Who would’ve thought Sandler could have pulled that out of me in a film with werewolves and Swiss-Army Thermoses?

So what does the future hold for Sandler and Happy Madison overall? For as lauded as their Netflix films have been, I’ve been continually surprised by the restraint they’ve shown, especially compared to the bulk of the company’s output. Will there be more schlocky low-brow fair like The Ridiculous 6, more solid character-based humor like Sandy Wexler or more middling, forgettable offerings like Father of the Year? While I still don’t know if there’s a foolproof formula to determine the type of production we’ll get, there’s bound to be surprises along the way.

  • “I’m Getting Paid How Much?!” Inexplicable Cameo Award: Lots of worthy contenders this week: Ray Liotta, despite being fourth-billed, barely has anything to do. It’s always fun to see players like Kenan Thompson, Melissa Villaseñor, Mikey Day, Kym Whitley, Lavell Crawford and Betsy Sodaro pop up, no matter how underutilized they are, but they make the most of their opportunities. But I’m giving the honors this week to Stiller, who appears at the open and sadly never returns.
  • Just Go With It – The Happy Madison Promise: Aside from the aforementioned references to Happy Gilmore and past films, nothing stood out too egregiously this time. Maybe it’s the Halloween spirit in me, and maybe it’s the knowledge that I’m done considering things like this, but I’m giving this one a pass.
  • Fart Joke Counter: Much like the lone, solemn teardrop on the Native American in the infamous anti-littering commercial, Hubie Halloween contains one solemn, lonely fart to round out this column.
  • The Walkout Test: This one’s an easy pass.
  • NEXT TIME: Join me for one final installment, as I give my rankings of all 46 (!) Happy Madison films that we’ve covered.