5. Jack and Jill (2011)
Let’s just skip over the fact that a pair of identical twins of different genders is something that has only happened around 10 times in history, and on every case the female ended up having a genetic disorder that made her really short and stopped her ovarian development – let’s call all that suspension of disbelief.
So even if you are willing to buy the idea that Adam Sandler, once again playing a successful businessman with a beautiful younger wife (Katie Holmes), has an identical female twin also played by Adam Sandler, and that this twin comes to visit and Al Pacino (playing himself) falls in love with her, Jack and Jill is still painfully unfunny and absolutely juvenile in its humor.
This could very well be the biggest concentration of fart and diarrhea gags, jokes on homeless people and Latino stereotypes we’ve ever seen on screen. It’s a wonder, really, that it took this long for Sandler to dress himself up as a woman and put on a “double performance” as a hook for audiences to buy their ticket to see Jack and Jill.
What’s a little harder to grasp is why in hell did Al Pacino signed up to play a heightened version of himself that falls in love with crossdressing Adam Sandler, really. The film won all the awards (yes, every single one of them) at the 2012 Razzies, marking Al’s first “win” in four nominations, and Sandler’s fifth Raspberry trophy.
The rare underperformer on Sandler’s career, Jack and Jill only made US$150 million dollars worldwide.
4. The Ridiculous 6 (2015)
The moment when bad Sandler movies stop being a funny target for Hollywood criticisms and become a frightening phenomenon is when The Ridiculous 6 is lauded by Netflix executive Ted Sarandos as the most watched movie ever on the streaming service. The picture, the first out of four Sandler has signed to make for Netflix exclusive releases, is a western parody directed by Frank Coraci (Click), and is regarded by some as a passion project for Sandler, a fan of the genre.
Unsurprisingly, though, the actor and the script don’t put up much of an effort to be genuinely funny or coherent throughout the film’s 2-hour running time.
A critic for Empire magazine noted that “the Native American people have suffered any number of indignities over the years. But they haven’t, until now, suffered Adam Sandler”.
The star’s unwillingness to spare a kind eye towards anyone but himself extends to Native Americans as he plays Tommy, a white man raised by Indians and contacted by his long-lost father when the old man need to pay a huge debt. Sandler and his five half-brothers (Terry Crews, Jorge Garcia, Taylor Lautner, Rob Schneider and Luke Wilson) then proceed to go on a mission to save their dad.
3. Billy Madison (1995)
Some people claim Billy Madison is Sandler’s finest film if you don’t count the dramas. And hey, those people have a point: as his first star vehicle after he left Saturday Night Live, Tamra Davis’ film carries a more innocent, less toxic version of Sandler’s unwavering machismo humor.
It also comes with some genuinely funny moments, especially when Sandler’s titular man-child gets to do the stupid stuff he really likes to do, like chasing a gigantic penguin down the driveway and dancing down a staircase to the sound of Culture Club’s “I’ll Tumble 4 Ya”. Those truly eccentric and weird elements are what drive people to claim this as one of the sole times Sandler got some bits right.
And while that is true, Billy Madison, seen today, is also a chilling preview of the kind of humor Sandler would bring to his later efforts. The homophobic jokes about Josh Mostel’s school principal and his “I’m horny” valentine notes to Billy and the infamous scene in which Sandler really hit kids as hard as he could while playing dodgeball for “authenticity” are as aggressively noxious as anything he would go on to do, and the fact that there are bright spots here and there not only fail to make the movie really compelling, but succeed in making it even more depressing to watch. Seeing what Sandler could have been in the light of what he was always set to become is not a pleasant ride.
2. The Cobbler (2014)
Rarely has a director bounced faster from an absolute and total disaster like The Cobbler – Tom McCarthy, this film’s director, went on to release Spotlight barely a year later, and we all know what happened then. Watching this weird bittersweet comedy, though, few people would have thought McCarthy had it on him to make another great film.
Here, Sandler plays a New York cobbler who finds a family heirloom capable of literally putting him on the shoes of his clients, watching life from their point of view. Instead of the sensitive and insightful themes McCarthy infused his previous movies with (see The Station Agent and Win Win), The Cobbler is mostly preoccupied with making everyone a shallow stereotype designed to assist on the protagonist’s journey of self-discovery.
Maybe McCarthy had the idea to cast Sandler in this part to try to subvert his persona and the toxic elements of his humor, but the gamble didn’t work, mostly because the script, penned by McCarthy and newcomer Paul Sado, has serious tonal issues and an approach to character that all but undermines the intelligence of the audience.
The rare Sandler movie to get exactly what it deserved at the box office, The Cobbler barely got a release, and has went largely unseen to this day, despite it being available on Netflix. Ah, justice, at last.
1. Going Overboard (1989)
Yes, Adam Sandler has gone on to make truly awful movies in his career, but none is quite a match to Going Overboard, the 1989 clunker produced before his Saturday Night Live stint, and thus before anyone had any idea who he was.
Valerie Breman, who would go on to direct the not-that-better Love & Sex, starred by Famke Janssen and Jon Favreau, fills her movie with off-the-wall imagery, a couple of dream sequences and even an animated portion, all to tell the mediocre story of Schecky (Sandler), a cruise ship waiter who dreams of being a comedian.
The ship’s resident stand-up funnyman, Dickie (Scott LaRose) rejects every attempt Schecky makes for a chance on the spotlight, and after a mix-up in which Dickie get stuck in a bathroom, the ship is attacked by the forces of General Noriega (Burt Young), who has a personal score to set with Miss Australia, who’s on board of the ship.
Going Overboard aims for that screwball energy of absurdist comedy, but what it gets is predictable jokes and character stereotypes, badly inept filmmaking, and a script as ridiculous as it is entirely unfunny.
Sandler seems uninterested and aware of the complete disaster he’s in at all times, and amazingly that doesn’t make it much better, neither does the supporting turns by Billy Bob Thornton and Billy Zane. So if you ever want to say anything nice about Sandler, say that his worst film is probably that bad because it was poorly made, not exactly because he was the star.
Author Bio: Caio Coletti is a Brazilian-born journalist, a proud poptimist, and has too many opinions to keep them all to himself.