"Saturday Night Live" is more than just a comedy show; it's a defining force in entertainment. Nearly fifty years after its debut, the series has brought forth some of the greatest comedic talents, from Bill Murray and Will Ferrell to Kate McKinnon. Over the years, the show has introduced thousands of unforgettable characters, many of which became cultural icons. However, among them, there are a few that raise eyebrows when it comes to taste and sensitivity.
Decades of shifting societal values have made some of "SNL"'s most iconic characters seem outdated, inappropriate, or even offensive by today's standards. That doesn't mean these characters weren't funny or undeserving of their place on the show—it's just that it's surprising to look back and see how much our collective sensibilities have changed. With that in mind, here are ten of the most controversial and, in some cases, downright offensive characters to ever appear on "Saturday Night Live."
10. The Samurai

Comedy was simpler in the '70s. A single racial stereotype could become the cornerstone of a hit sketch. No need for late-night brainstorming sessions—just a quick compilation of exaggerated Japanese gibberish, and the sketch was ready to air. The prime example of this easy formula was John Belushi's beloved character, the Samurai.
The Samurai would show up in a different profession each time—sometimes a hitman, hotel manager, or disco dancer—but the humor always relied on the lowest common denominator. The concept was simple: a medieval samurai somehow finds himself in the present day with a new job. That was the entire gag. Belushi fully committed to the role physically, as always, yet his character rarely spoke. Instead, his dialogue was just a string of exaggerated Japanese-sounding noises. Ultimately, each sketch would meander to an abrupt conclusion, lacking structure or real substance, with nothing more than a silly accent and sheer humiliation.
9. The Continental

Christopher Walken has been a guest on "SNL" seven times, which has led to the creation of his own recurring sketch character. The Continental, a bumbling, somewhat sketchy man of mysterious origin, serves as a constant wellspring of uncomfortable humor that now resonates with the #MeToo movement.
Each Continental sketch begins with the character awkwardly attempting to host a date in his lavish hotel suite. However, his actions quickly take a turn when the woman decides to leave, horrified by his creepy advances. His frequent references to stalking, drugging, and even chloroforming her only serve to make her want to flee. Yet, when she tries to leave, the Continental always manages to block her escape, even going as far as locking her in and attempting to swallow the key. What makes it worse is that the camera adopts the woman's perspective, placing the audience right in the middle of this sleazy and unsettling scenario.
8. The D-ck in a Box Dudes

Speaking of unsettling older men, we can't overlook 'D-ck in a Box.' One of The Lonely Island's most famous songs, 'D-ck in A Box,' featuring Justin Timberlake, continues to be a popular rewatch and singalong. While it’s undeniably catchy and fun, it also carries an uncomfortable and inappropriate tone.
The premise of 'D-ck in a Box' revolves around a simple, albeit disturbing, question: How do you get a woman to look at your genitals? It’s a question that has been addressed before, often through the classic move of flashing with a trench coat. However, that approach always came with some inconvenient labels like 'flashing,' 'indecent exposure,' and 'non-consensual.' Ultimately, our bold protagonists discovered the solution: hide your penis in a box and present it as a gift to a woman who is expecting something nice, leaving her doubly disappointed.
7. Stefon

Bill Hader's portrayal of Stefon is often considered one of the best recurring characters in 'SNL' history. The unique excitement that Seth Meyers brought to the sketches whenever Stefon appeared was unmatched. Despite the character's comedic success, there were some troubling aspects to his portrayal.
For one, like many 'SNL' characters, Stefon’s stereotypical depiction of homosexuality was often used as the punchline. Additionally, Stefon repeatedly used the term 'midget' throughout his appearances, even though by the time he first used it, the term had already been widely recognized as inappropriate. Even within the sketch's narrative, Seth Meyers repeatedly informed Stefon that the word was offensive, but Stefon ignored this. At one point, Stefon did amend his language, replacing 'midget' with 'fun-sized.' The character also had a recurring plotline in which he attempted to seduce Meyers, based on the problematic notion that 'no' really means 'yes.'
6. Stuart Smalley

Unlike Stefon, whose homosexuality was only one facet of the character, Stuart Smalley was defined by his sexuality—and that became the primary punchline. Of course, there was also the running gag of Smalley’s father being an alcoholic (ha?). But the underlying reason for his father’s alcoholism was that his son was gay, which brings us right back to square one in terms of comedy.
Stuart Smalley, brought to life by future (and now former) senator Al Franken, spoke with a stereotypical lisp, sported Malibu Ken-style outfits, and was incredibly in tune with his emotions. In the 90s, that was enough to make him a memorable and ongoing joke. In one sketch, Smalley discusses his father’s abuse of both him and his mother, and because Smalley was too effeminate to stop it, it’s (at least theoretically) played for laughs.
5. Pat

When viewers revisit old sketches and exclaim, “Man, that wouldn’t fly today!” there’s a solid chance it was a Pat sketch. Played by the often-underrated Julia Sweeney, Pat’s entire character—every single aspect of their being—was based on the ambiguous presentation of both man and woman.
Pat had an androgynous name, dated others with androgynous names, wore androgynous clothes, and adopted androgynous habits. The entire concept was built on the now-outdated idea that gender was strictly binary and rigid. In reality, even in the 90s, people weren’t divided into clear-cut categories like football players and ballerinas, but in Pat’s world, that fact went unnoticed. The sketch did manage to create a fun dynamic where the supporting cast would slyly try to extract information to confirm Pat’s gender, which was at least a bit more engaging than the Samurai, who mostly just did samurai things.
4. Governor David Paterson

Some characters on this list are one-dimensional and offensive—such as the Samurai, Stuart Smalley, Pat, and, as we’ll get to, the Ambiguously Gay Duo. However, only one character manages to hit the trifecta of being one-dimensional, offensive, and based on a real person: Governor David Paterson, as portrayed by Fred Armisen.
David Paterson was the actual Governor of New York State during the late 2000s and was legally blind. For “SNL,” this became a prime opportunity for a series of jokes centered on his disability. The sketches would depict Paterson bumping into furniture, using binoculars to read, and clumsily stumbling around in front of the camera, unaware of his surroundings. At least Armisen was able to showcase his excellent physical comedy skills in the process.
3. Canteen Boy

Despite all the controversial sketches, there's one clear frontrunner: Canteen Boy. While most of his appearances were offensive due to mocking the mentally challenged (regardless of the disclaimer), there’s one particular sketch that crosses the line entirely. It's so offensive that it’s been scrubbed from YouTube, with only third-party mentions surviving. The sketch in question features Alec Baldwin as the leader of Canteen Boy’s scout troop, where, unsurprisingly, he attempts to molest him.
In this disturbing sketch, Baldwin spends the night in the woods with Canteen Boy and aggressively tries to seduce him, regardless of the scout’s mental disability. He strips off his own shirt, tries to get Canteen Boy drunk, forces him into a sleeping bag, cuddles him, and even sucks on his finger. The timing of this sketch was particularly insensitive, as sexual assault allegations involving scout leaders were widespread at the time. For victims and their families, this sketch was a deeply offensive mockery. And no matter when it's aired, jokes about molesting the mentally disabled are bound to trigger justified outrage.
2. The Ambiguously Gay Duo

Following Stefon and Stuart Smalley, we come to one of the most offensive recurring “SNL” sketches of all time: The Ambiguously Gay Duo. Created by Robert Smigel and voiced by Stephen Colbert and Steve Carell, this sketch featured a pair of muscular male superheroes who were blissfully unaware of how their actions oozed homoerotic undertones.
A parody of early Batman and Robin, the duo delivered a never-ending stream of catchphrases that were as energetic as they were nonsensical. The twist? Every phrase and every superhero move had an undeniably gay edge to it.
The duo drove a car shaped like a penis, flew by riding on top of each other, dodged bullets with ballet moves, and defeated villains by inserting various penis-shaped objects into equally shaped butt objects. The humor came from their complete lack of awareness of how all of this appeared, and as offensive as it all was, the jokes continue to be effective even today.
1. The Word Association Guy

This sketch, airing during “SNL”'s inaugural season, featured Chevy Chase as a man conducting a job interview with the prospective hire, Richard Pryor. The two engage in a word association game that quickly escalates.
The exchange grows heated as they toss racial slurs back and forth, culminating with Chase uttering the full, uncensored n-word on primetime network television. The sketch is fast, straightforward, humorous, and embodies the rebellious spirit of early “SNL.” It remains a historic TV moment, not in spite of but because it went farther than any sketch has dared to go before or since.
