People tend to rag on Adam Sandler these days, and to be fair, he's kind of an easy target given his movie output in the last decade or so. But there was a time when he was one of the biggest stars around, and for good reason-- his stint on Saturday Night Live and his movies in the '90s made a whole generation laugh until they peed their pants. And as we all know, you ain't cool unless you pee your pants.
While Sandler tends to be associated with PG-13 or tamer comedies, he wasn't without his inappropriateness during his '90s heyday. The very adult content on his comedy albums are an obvious source of edgy material that we can't believe he got away with, but he also managed to sneak a lot of gags into his more family-friendly projects that make our jaws drop when we look back on them today. This list includes shudder-worthy jokes that he either said himself, or he wrote for someone else to say.
20 "Now, You Will Go To Sleep...Or I Will Put You To Sleep"
Ben Stiller certainly stole every scene he was in during his cameo in Happy Gilmore, and he spouted off some of the movie's most-repeated one-liners. But the actual nature of his character is pretty cringeworthy when you really think about it: He was responsible for forcing the elderly people of his nursing him into labor servitude, and it is heavily implied that he takes a hand to them if they get out of line.
19 "Stop Making Fun Of Me"
No matter how you slice it, The Waterboy's Bobby Boucher is a character with serious social issues, if not actual mental illness. Sure, he ends up getting his revenge on his bullies and becoming a hero, but that doesn't change the fact that the entire movie revolves around making fun of him for his social and emotional issues. There's also the uncomfortable matter of how many people use his uncontrollable rage to their own ends, rather than helping him find a healthier outlet for it.
18 "I'm Glad I Called That Guy"
Only in a world before there was a different mass shooting on the news every other week could a movie make a punchline out of a disturbed, armed individual with a long list of people he plans to take out. In the case of Steve Buscemi's Billy Madison cameo, turning a future mass shooting into a silly joke-- and have that shooter save the day during the climax of the movie-- comes off as extremely insensitive, especially in retrospect.
17 "I Can't Believe Tyson Gave That Girl..."
Adam Sandler quickly established himself during his tenure on Saturday Night Live as the guy who sings goofy songs on "Weekend Update." In fact, two of his songs-- The Hanukkah Song and The Thanksgiving Song-- have both become modern classics for their respective holidays. But the latter tune, like most of Sandler's songs, contains a lot of random lyrics that are only there for the sake of an easy rhyme and an edgy joke, including a bit that uncomfortably makes light of Mike Tyson's sexual assault conviction.
16 "I Want You, Billy"
Just because Adam Sandler is an adult in Billu Madison doesn't mean that the faculty of the elementary school he is attending shouldn't still treat him like any other student. His completely unethical relationship with Ms. Vaughan aside, the school's principal comes on to Billy pretty aggressively, and in doing so via a cute Valentine card it all feels a little bit uncomfortable given the context and his job.
15 "Pull A Rabbit Out Of My..."
One of Adam Sandler's most popular characters on SNL was Opera Man, where he sang about the events of the week in a ridiculous accent. Opera Man definitely get edgy pretty regularly and sneaked a lot of vulgar jokes into his tunes-- including the time he ended a song by saying he was going to pull a rabbit out of a certain orifice, followed by him pretending to do so as he produced a stuffed animal from his lap.
14 "I Still Get Weirded Out When They Kiss"
Big Daddy marked Adam Sandler's first attempt to write and star in a movie that was a little more "grown up" and featured a less gimmicky premise and a cast of more realistic characters. His heart was definitely in the right place when he had two of his male cast mates play a gay couple, but he still seemingly couldn't resist also making them the butt of a lot of cheap jokes that already felt tone deaf in 1999.
13 "Fatty McGee, You're The Fattest"
Adam Sandler doesn't get enough credit for how funny his comedy albums are, especially the first few. His debut, They're All Gonna Laugh At You!, was a huge hit and proved that Sandler could have both #1 movies and #1 albums simultaneously. However, not all of the skits on that album were comedy gold-- one particularly unfortunate one, "Fatty McGee," has Sandler playing an overweight man who can't catch his breath after walking up the stairs. That's literally the entire premise. It was just mean-spirited, especially for someone who was buds with Chris Farley at the time.
12 "Then The Show Must Go On"
Most of Adam Sandler's SNL characters were either over-the-top caricatures or low-key sad sacks. The most iconic example of the latter has to be Barry, who was the star of "The Denise Show," an apparent public access show all about the woman who dumped him. It initially seems like a humorous look at teenage heartbreak, but it very quickly becomes apparent that Barry is basically a stalker, and that his obsession is verging on taking a very dark turn-- not exactly hilarious territory.
11 "Find Your Happy Place"
Adam Sandler managed to follow up the hit Billy Madison with the even bigger-- and most would probably agree, even funnier-- Happy Gilmore. For the most part, the jokes and gags are way less juvenile and inappropriate than Billy Madison (which will be on this list multiple times), but it didn't completely avoid jokes that should've been rethought. Mainly, the "happy place" that Happy goes to in his mind, which includes the cheap and offensive joke of a little person riding a tricycle for Happy's own amusement.
10 "Ben Franklin Is The Devil"
When The Waterboy isn't making fun of the struggles of Bobby Boucher, it is painting a pretty unflattering picture of the residents of Louisiana. The peripheral characters of the film are mostly stereotypes of backwoods, inbred, highly uneducated buffoons with over-the-top accents (including one character nobody can understand). And Bobby's mother, gamely played by the always-reliable Kathy Bates, checks off all the boxes of the worst cliches of a Cajun.
9 "Do It For Mama"
As a whole, Adam Sandler's second album, What The H-- Happened To Me?, is far less reliant on cheap sexual humor than his debut was. But that doesn't mean there isn't any vulgarity to be had, including the track, "Do It For Mama." The entire premise of the skit is that Sandler plays an overbearing mother whose answer to all of her children's problems is telling them to...explore themselves, to put it as G-rated as we can. That it's an adult badgering children to commit this act in front of each other is already gross enough, but that she's their mother just gives it a whole other level of nope.
8 "Full Of Shame"
At a certain point, Adam Sandler's comedy albums devolved into how far he could push the envelope, often without actually trying to build a clever premise out of it. Such is the case with "The Peeper," which takes place from the perspective of a peeping tom as he watches a woman undress and eventually runs afoul of her husband, relaying his disgusting thoughts to the audience in the process. Again, there are some things that you just don't joke about, and certain types of "characters" that shouldn't be mined for comedy.
7 "It Reminds Me Of The Time..."
There are a lot of references that overlap between Adam Sandler's movies and his albums, such as the idea that school janitors have sideburns, or a fascination with 60-year-old guys. The way that manifests itself on the album side of things is in a skit on What The H--- Happened To Me? when a group of friends share stories that inevitably lead to weird interactions with 60-year-old men. The worst one involves intercourse that may not have been consensual, and possibly in the view of children-- neither topic of which is remotely funny.
6 "What's Today?"
In order to immediately set the scene that the titular character in Billy Madison is listless and without responsibility, he has no clue what day it is-- one of his friends suggests the day is "October"-- and he eventually realizes that the day only rings a bell because it's "nudie magazine day." What follows is Sandler rifling through a series of magazines that first includes a gag at the expensive of gender fluidity (implying that it is disgusting), and then a touch of ageism.
5 "Close Your Eyes...I'm Recording Something"
In a skit on one of his albums, Adam Sandler plays Barry Lakin, a man who is going around to strangers and the street and seeing if they can tell from an audio recording if two people are engaging in intercourse or are simply working out in a gym. Eventually, he comes upon an attractive young woman, which prompts Barry to tell her to close her eyes and then he proceeds to pull down her pants and have intercourse with her without her permission. That the female character is made to seemingly enjoy the unsolicited act does little to diminish the creepiness of the "joke."
4 "Good Morning, Students And Faculty"
Even though there was a parental advisory sticker on the cover of Adam Sandler's first comedy album, nobody expected just how vulgar it was going to be. But Sandler wanted to make sure everyone who was listening knew what they were getting into immediately, as the album opens with an astoundingly disgusting skit where an assistant principal is filling in for the regular principal, and proceeds to announce his new policies which involve the students showering together and performing inappropriate acts in front of him. Considering colleges don't generally have principals, at "best" this skit is to involve high school students, only a small percentage of which aren't minors. Yikes.
3 "So Sorry To Interrupt!"
A recurring character in Billy Madison is the imagined giant humanoid penguin that Billy has concocted in his various drunken stupors. At one point, he thinks he has stumbled in on the penguin enjoying a romantic evening with his girlfriend, but that isn't even the worst of it. Near the end of the movie, the penguin and the bus driver (played by Chris Farley) embrace and begin to make out in R-rated fashion, complete with the penguin doing something to Farley's character just off screen that isn't at all subtle and shouldn't have been allowed in a PG-13 movie.
2 "My Beard Is Scratchy"
One of the most infamous skits in all of SNL history is the "Canteen Boy" scene starring Adam Sandler and Alec Baldwin, the latter of which plays the adult scout leader to Sandler's young boy scout. The entire scene is built around Baldwin's character seducing Canteen Boy in no uncertain terms-- culminating in the two snuggling in a sleeping bag and Canteen Boy making a horrifying discovery in there. Considering that the actual Boy Scouts of America have run into controversy with that sort of thing, the set-up here was perhaps a little too "real" to be played for laughs.
1 "My Little Chicken Likes To Wear Garter Belts"
What could possibly outrank "Canteen Boy" on a list of jokes Adam Sandler probably shouldn't have gotten away with? That's easy-- the song "My Little Chicken," which wouldn't have been as bad if it were only on one of his albums but he actually performed it on SNL. Just what is so bad about it? Let's just say that the song is about Sandler's intimate relationship with an actual chicken, including a shockingly vulgar line about where eggs come from and where Sandler wants to go.