“Saturday Night Live” has been a comedy institution since 1975. It’s helped launch the careers of some of the biggest names in the entertainment business, from Bill Murray to Adam Sandler, and brought quotable lines like “Schwing!” and “We are two wild and crazy guys!” to the modern pop culture lexicon. Even if you don’t watch regularly, there’s a good chance “SNL” has influenced your life in one way or another, and plenty of folks likely have fond memories of watching the show growing up. 

Advertisement

But as is the case with anything that’s been around for several decades, not everything from “SNL” has aged so well. The late night sketch series has its share of moments it’d probably want you to forget, many of which were hilariously eulogized during the “SNL 50” anniversary celebration. Whether it’s jokes that have aged poorly or gags that should have been instantly questionable, to the point where you really have to ask yourself what the writers and performers were thinking, here are 15 of the most controversial “SNL” sketches and moments.

In the summer of 2020, amid the Black Lives Matter protests following George Floyd’s murder, many networks and streaming services took down episodes containing white actors sporting blackface. Blackface dates back to the 19th century, where white actors would put on black makeup for minstrel shows and talk in a stereotypical black manner. The practice has always been demeaning, and now, episodes of “Scrubs” and “30 Rock” are almost impossible to find for their inclusion of blackface, even if they had more of a satirical bent. Jimmy Fallon got ample pushback after an old sketch from 2000 resurfaced of him in blackface impersonating Chris Rock. 

Advertisement

The sketch sees Fallon impersonate Rock while talking about crack cocaine, and upon social media going into a frenzy, Fallon issued an apology on X (formerly Twitter): “In 2000, while on SNL, I made a terrible decision to do an impersonation of Chris Rock while in blackface. There is no excuse for this. I am very sorry for making this unquestionably offensive decision and thank all of you for holding me accountable.” Rock, also a former “SNL” cast member, didn’t harbor any ill will toward Fallon, telling The New York Times, “A lot of people want to say intention doesn’t matter, but it does. And I don’t think Jimmy Fallon intended to hurt me. And he didn’t.”

In 2009, following revelations of Tiger Woods’ infidelity toward his wife, Elin Nordegren, who allegedly responded by assaulting him, “SNL” decided to poke fun at the situation. Even though there’s not really anything funny about cases like this, a grinning Nordegren (played by guest host Blake Lively, making this even more awkward) stands next to a severely injured Woods (Kenan Thompson), wearing an arm sling and bandages across his face.

Advertisement

While the joke seems to be an embittered wife getting revenge on her cheating husband, it also makes light of actual victims of domestic violence. Rita Smith, the National Coalition of Domestic Violence president at the time, released this statement (via The Boston Herald): “There’s nothing funny about this story, particularly if violence was part of the events that took place. It diminishes people’s support for victims of domestic violence.”

It’s a shame this particular sketch was part of the evening’s festivities because the episode stands as one of Lively’s best performances across film and TV. “SNL” might be known for having topical humor, but this is a story they probably should’ve stayed away from.

Advertisement

In 1992, “Saturday Night Live” aired a “Wayne’s World” sketch that sees Wayne (Mike Myers) and Garth (Dana Carvey) run down 10 things they love about then-president-elect Bill Clinton. If you try to rewatch the sketch today, you’ll notice they say nothing about “Chelsea” being at number two. That’s because they said some not-so-excellent things about the future President’s daughter, who was only 12 years old at the time. 

Advertisement

In the episode’s original airing, Wayne mentions how “adolescence has been thus far unkind” to Chelsea Clinton, but that it’s all good because she’s “going to be a future fox.” No one should be talking about how a preteen could be hot after growing up, and the Clintons were understandably miffed. President Bill Clinton weighed in on the controversy to People: “The ‘Saturday Night Live’ skit where I was in McDonald’s talking about Somalia — I thought that was hilarious. But I think you gotta be pretty insensitive to make fun of an adolescent child.”

Both Myers and “SNL” creator Lorne Michaels apologized for the joke, and making fun of presidents’ kids has continued to be off-limits. In 2017, “SNL” writer Katie Rich was suspended from the show after tweeting a joke at the expense of Barron Trump. 

Advertisement

The distinction of worst “Saturday Night Live” sketch ever might go to 1980’s “Commie Hunting Season” with host Malcolm McDowell. The sketch involves a bunch of rednecks wanting to shoot and kill communists at a demonstration, which is already iffy territory, but then Uncle Lester (Charles Rocket) says this in response to how to kill commies if a demonstration isn’t happening: “Alls you got to do is shoot yourself a Jew or a n***** — chances are better than even you’ll be shooting a commie anywho.”

Advertisement

You could hear a pin drop from the audience, who barely laugh throughout the entirety of the sketch. According to “Saturday Night Live FAQ: Everything Left to Know About Television’s Longest Running Comedy,” the network received 150 complaints about “Commie Hunting Season.” It’s an awful sketch, and it squanders Malcolm McDowell’s talents, likely explaining why he never returned to host “SNL” again.

Before Adam Sandler was fired from “Saturday Night Live,” he created many memorable recurring characters, like Opera Man, Cajun Man, and most controversially, Canteen Boy. The not-so-young boy scout had popped up a few times over the years, but in 1994, he was part of a sketch where he’s on a camping trip with some of his fellow scouts. Their scoutmaster, played by Alec Baldwin, requests some alone time with Canteen Boy and proceeds to make unwanted sexual advances on the scout.

Advertisement

Previous Canteen Boy appearances do establish that he’s an adult, but given his mannerisms and the power dynamic, it’s understandable if many “SNL” viewers believed he was an underage boy. The Boy Scouts of America also took great offense at the sketch, releasing this statement (via The Washington Post): “We see nothing funny about child molestation, and are surprised that this unfunny subject would be selected for a comedy sketch.”

Claudine Longet was an incredibly minor celebrity in the 1970s who was catapulted into greater fame when she was arrested and charged with the murder of her husband, professional skier Vladimir Sabich. Longet attested that the gun went off accidentally when Sabich was showing her how to use it, and with such a dubious story, “SNL” decided to have some fun that would culminate in the show’s first ever on-air apology.

Advertisement

1976’s “The Claudine Longet Invitational” shows footage of men skiing down slopes until the sound of gunfire is heard and they fall into the snow, accompanied by stoic commentary from Chevy Chase and Jane Curtin. Longet’s case hadn’t even gone to trial at that point, so apparently, her lawyers confronted “SNL” over the sketch. The show issued an apology in the following week’s episode. 

Longet’s trial eventually took place a year later where she was found guilty of criminally negligent homicide, which entailed a $250 fine and 30 days in prison. Between that and an “SNL” sketch, she didn’t make out too bad from the situation.

In general, comedy works best when it’s pointing out foibles and hypocrisies within the powerful. Making fun of marginalized groups isn’t fun for anyone, which makes a 2007 sketch featuring Rainn Wilson somewhat baffling. 

Advertisement

Wilson, along with Bill Hader, Will Forte, and Jason Sudeikis, play some buddies drinking beer and singing along to “Danny’s Song” by Loggins and Messina. In between singing the chorus, each one offers an anecdote of what the song reminds them of, and naturally, they’re all pretty unhinged. But Hader’s character’s story involves having a fun day at the park with his father and not caring for once that his dad has Down syndrome.

The National Down Syndrome Society released a statement following the sketch’s airing (via The Times of Northwest Indiana): “[Individuals with intellectual disabilities] deserve to be respected and celebrated for their success and achievements, and not to have their clinical diagnosis used as a punchline.” In response, “SNL” bleeped out “Down syndrome” in future cable broadcasts of the episode, and it’s been cut entirely from Peacock.

Advertisement

In many cases, a controversial “SNL” sketch remains contentious years later, or maybe society only recognizes it as offensive when attitudes change. But Sinead O’Connor’s infamous 1992 musical performance is the rare instance where it drew heated arguments at the time, but the public now realizes how she was in the right all along.

Advertisement

O’Connor performed a cover of Bob Marley’s “War,” which ended with the singer producing a photo of Pope John Paul II, tearing it up, and saying “Fight the real enemy.” Public outrage was swift, and O’Connor’s career would forever remain dogged by the moment. The following episode had Joe Pesci hosting, and he stated how he would’ve smacked her if he had been there the previous week.

Over 30 years later, O’Connor’s “SNL” performance is recognized as one of the bravest acts in TV history. She was willing to call out the Catholic church during a time when it wasn’t popular and before many were fully aware of its atrocities concerning child abuse. It’s the rare example of a controversial moment actually aging better with time, and O’Connor deserved so much more support in the immediate aftermath of her protest. 

Advertisement

“SNL” may air late in the evening, but there are still standards and practices performers need to abide by. Failure to do so has landed a couple of performers in hot water over the years, and even the “SNL” audience recently crossed a line with hilarious results.

Advertisement

Season 6 was a contentious time for “SNL” already with Lorne Michaels’ temporary departure, and despite Charles Rocket being set up as a future breakout star, he wouldn’t last another season. Perhaps feeling as though his time was running out, Rocket improvised a profanity during a “Dallas” parody sketch. When someone asks him how he feels after being shot, Rocket replies, “It’s the first time I’ve ever been shot in my life. I’d like to know who the f*** did it.”

It wouldn’t be the last time a cast member swore, as Jenny Slate also dropped an f-bomb during her first and only “SNL” season when she told another character, “You stood up for yourself, and do you know what? I f***ing love you for that.” Despite most people assuming she was fired for the blunder, the real reason Slate left “SNL” was because she just wasn’t a good fit. Seeing as she found great success elsewhere, maybe it was all for the best. 

Advertisement

Some of the funniest Norm Macdonald moments ever came from his tenure on “SNL.” In particular, his “Weekend Update” jokes at the expense of O.J. Simpson are the stuff of legend with such bits as, “This week at the O.J. Simpson trial, the infamous bloody glove was finally introduced into evidence. And O.J. didn’t help his case any by blurting out, ‘There it is, I’ve been looking all over for that thing!'”

Advertisement

Sadly, not everyone appreciated his remarks, like NBC executive Don Ohlmeyer, a friend of Simpson’s. While the official reasoning for Macdonald’s firing was declining ratings, it seems as though Macdonald struck a sour note with Ohlmeyer, and Lorne Michaels had no choice but to let him go.

It’s a decision that would come back to bite Ohlmeyer, as Macdonald trash-talked the exec any chance he got. Macdonald got the last laugh when he came back to host an “SNL” episode a year after getting fired, proving how it’s never a good idea to pick a fight with a comedian. 

In 2019, Lorne Michaels was apparently furious at having to fire Shane Gillis from the cast before the new season even began after some of his racist and homophobic jokes resurfaced. Some of his racist jokes contained Asian slurs, and it kind of goes to show how far the show had come since the 1980s when Dana Carvey pulled off a racist impression of a Chinese man named Ching Chang.

Advertisement

Ching Chang showed up in three sketches total and featured Carvey using a wildly racist Chinese accent while wearing horn-rimmed glasses and sporting a bowl haircut. It’s the kind of ridiculously out-of-date character “SNL” could only get away with decades ago, along with the likes of John Belushi playing a samurai and Mike Myers playing a Japanese game show host. 

Maybe “SNL” didn’t want to risk repeating the mistakes of the past by having Gillis come aboard and risk offending various demographics. While “SNL” has gotten more diverse in its cast line-up since the ’80s (if only just barely), it’s good to see some progress getting made that these kinds of characters are unthinkable nowadays. 

Advertisement

With some controversial “SNL” sketches, you can at least kind of see the kernel of the idea where someone may have thought the idea was funny at one point. But season 20’s “Melanie Babysits” sketch might be one of the most uncomfortable things put to television, which could explain why it’s virtually impossible to watch today.

Advertisement

Dr. Henderson (Chris Elliot) offers to drive the babysitter Melanie (Mark McKinney) home for the night, and while driving her home (where it’s questionable if she’s even 18 or not), comments on her body. He also offers her alcohol and eventually pounces on her before the sketch cuts away to Dr. Henderson in prison screaming, “I’d do it again! I swear to the Lord above, given the chance, I would do it again! Do you hear me, society?! I’d do it again! And again! And again! And again!” There really aren’t any jokes to speak of in the entire sketch, and it ends with the implication that the father sexually assaulted a young girl. It’s probably for the best if this gets lost to the annals of time.

Advertisement

Jessica Simpson may have risen to fame first in the early 2000s, but it didn’t take long for her younger sister Ashlee to match and exceed those heights. Her music had a bit more of an edge to it, which was still a notch below Avril Lavigne mind you, but she could’ve had a very successful career in the realm of pop-emo music. A stellar performance on “SNL” could’ve sealed the deal, but instead, it tarnished her image.

Advertisement

Ashlee Simpson was set to perform two songs on a 2004 episode. She performed “Pieces of Me” without issue, but when it came time later in the episode to do “Autobiography,” the vocals for “Pieces of Me” were heard. To cover up the faux pas, Simpson did a little jig, but everyone watching at home knew what was up. She had been lip-synching the entire time. At the end of the episode, Simpson made the excuse that her band had started playing the wrong song, but she’d eventually state that a sore throat necessitated the lip-synching.

Simpson would redeem herself on “SNL” in 2005, but the damage to her career was done. Her subsequent albums wouldn’t be met with the same level of excitement as her first outing, and even though it’d be unfair to blame it all on “SNL,” a singer who doesn’t sing live isn’t the kind of image an up-and-comer needs.

Advertisement

“SNL” has veered into uncomfortable territory in the past, and the 2017 Safelite Autoglass sketch definitely falls into that category. The bit involves a SafeLite technician, played by Beck Bennett, repeatedly breaking a woman’s windshield, so he has an excuse to talk to her underage daughter. He at least gets some comeuppance at the end with the mother beating him up, but it’s yet another wildly uncomfortable sketch that’s all the more shocking that they used a real brand for the backdrop.

Advertisement

Naturally, the sketch caught Safelite’s ire, as the company took to X, formerly known as Twitter, to write, “Thanks for the skit. Although we can take a joke, this one was a step too far. Our techs are our heroes. #notcool.” “SNL” frequently uses real brands in its sketches, but their employees aren’t generally portrayed as perverted as this. Perhaps to avoid any further action from Safelite, “SNL” removed the video from future reruns.

During the “SNL 50” anniversary special, the show presented a montage of controversial moments throughout the show’s history, many of which are on this very list. The show also owned up to platforming performers who have since wound up in legal trouble, like Robert Blake and Diddy, but the one glaring omission in this segment was not including Donald Trump hosting in 2015. 

Advertisement

It felt controversial to have a presidential candidate host the show in the middle of an election, giving him an exorbitant amount of airtime. Many performers and writers have criticized the show for making the move, including former cast member/writer Tim Robinson who felt that Lorne Michaels had “lost his f***ing mind” letting Trump host (via The Daily Beast).

Regardless of how one feels about President Trump, he’s a convicted felon who under normal circumstances probably should’ve been included in that “SNL 50” retrospective of shame. And his tenure as “SNL” host raises a bevy of questions as to what the show’s responsibility in platforming political candidates should be.