The Worst Adam Sandler Films: 'Chuck and Larry,' 'That's My Boy,' '

In these days of ‘Pixels’ eliciting despondent reactions worldwide, and ‘The Cobbler’ looming threateningly among your suggested Netflix titles, we felt that it was time to take stock of how we got here. Some of our staff bravely agreed to speak to their worst Sandler-based cinematic experiences.

That’s My Boy (2012)

Corban Goble: It might be hard to believe, but a comedy pinned around Adam Sandler and Andy Samberg wasn’t that bad of an idea in 2012. After all, these two were responsible for You Don’t Mess With the Zohan and Hot Rod, two of the greatest films ever made — one could reasonably expect an oddball gem.

However, the characters in That’s My Boy are despicable. You get some of your worst Sandler ever as the shithead former rocker Donny, and some of your worst Samberg as he plays the straight man son Todd for some reason. (Samberg also played the straight man in Celeste & Jesse Forever, another promising-on-paper comedy that turned out super ehhhh). There’s no redeeming weird-out scene. Leighton Meester and Ciara are in it though!

Click (2006)

Andrew Burmon: An entire movie based on a sentence Seinfeld probably scrubbed out of a Word 2000 doc (“How universal can a universal remote really be?), 2006’s Click made Kate Beckinsale, who kills vampires and studied Russian lit at Oxford, into some primordial precursor to Leslie Mann’s Funny People harpy and Christopher Walken, who made The fucking Deer Hunter, into Christopher Lloyd’s understudy.

What’s remarkable about the film is that its attempt to make cancer into a rimshot is the least offensive thing about it. The fundamental theory of fate posited by Click is that members of the middle class will always lead essentially the same lives regardless of contingency. If this is true — and maybe it is — that’s the sort of heavy revelation that shouldn’t be delivered via Henry Winkler cameo. The most winning element of the movie? The fat jokes, which were tautological at best and scatological at worst, but seemed to come from a place of very genuine callousness.

Mr. Deeds (2002)

Neel Patel: There are two kinds of Sandler movies: the ones where he’s playing a crazy/quirky/bizarre character navigating through a normal world, and the ones where he’s the normal one trying to deal with the crazies. The remake of Mr. Deeds is something like the former, except you don’t have enough crazies. You need fun characters to play off of, and while Jon Turturro as Emilio the butler is the closest we get to that, it’s not enough. Sandler’s boring in this movie, and so is the rest of the cast. Usually in his movies, we’re inundated by just a rainstorm of fucked up shit—instead, in the PG Mr. Deeds, we just get a view of why New York City is a depraved hell hole. I mean, it definitely is, but who the fuck cares if we can’t laugh about it?

Also, Al Sharpton. Why.

I Now Pronounce You Chuck and Larry (2007)

Winston Cook-Wilson: I would argue that there is little in Sandler’s later oeuvre that can rival the abhorrence of Chuck and Larry. Just a cursory glance at an On Demand summary will make clear how misguided and offensive this film is even on the most rudimentary level. In need of a primary beneficiary to ramp up his life insurance, fireman Sandler decides that he needs to enter a domestic partnership. So of course, he ends up having to do this with his dankest fireman bro, KJames — the kind of bro that will do anything for his boy.

And we’re off! James falls for a woman, and stops keeping up appearances with Sandler. Thus, behold, these fake gay men start squabbling like a married couple! Sandler is insisting on more public seven-minutes-in-heaven moments. Just imagine if you, heterosexual white male target audience, were in this position! It’s cool — C&L have gay friends. Lance Bass (you know, the non-straight NSync member) sings at the end.

Also Rob Schneider turns in a lethal performance as “Asian Minister”; it’s just another in a long line of racist Schneider cameos in Sandler vehicles. Hitchcock appeared as an extra in his films, and Schneider appears in race makeup in Sandler joints. That’s life.

Happy Gilmore (1996)

Matthew Strauss: If pressed to choose an iconic Sandler flick, I imagine many would pick Happy Gilmore from The Golden Age of Adam. Sandler, himself, would probably throw it in a Top 3, given that he named his production company Happy Madison. Happy Gilmore has certainly improved with age, but more likely from forgetting its details than anything akin to it being quality cinema. If nothing else, Happy Gilmore deserves its nomination as Sandler’s Worst simply because of the garbage that it created — what it gave Sandler the freedom to do afterward. Shooter McGavin is the movie’s asshole villain, but frat bros everywhere still think he’s great! With Happy Gilmore, Sandler spawned a generation of douchebags who call out McGavin for beer pong and think that golf is something easy you can play drunk. It’s not. Golf is hard. Fuck this movie.

Billy Madison (1995)

Sean Hutchinson: I’ll go one step further with what Matt was getting at and say BIlly Madison, which was released earlier, is simultaneously Sandler’s worst and best movie. It’s his best because he was able to capitalize on his schlubby yet endearing puppy dog persona from SNL and actually make a funny movie, but it’s his worst because it established a bar that was set far too high that he never really hit again. It was the thing that made Sandler super famous, which means it’s the reason he became exceedingly lazy with every movie since then. Blame Billy Madison for Jack and Jill, Grown Ups (1 and 2), Pixels, and for the atrocious Netflix deal that will keep Sandler rolling out unambitious comedies that get by on fart jokes, racial stereotypes, and gibberish for a long time to come.