Top 20 Darkest SNL Sketches Ever

Welcome to WatchMojo, and today we’re counting down our picks for the Top 20 Darkest SNL Sketches Ever. For this list, we’ll be looking at the best “SNL” skits that tackle disturbing subjects while still being funny. Did we forget any shocking sketches? Let us know in the comments below.
#20: “Farewell Mr. Bunting”
“Dead Poets Society” receives both a loving and horrific adaptation in this sketch. Fred Armisen plays a character loosely modeled on Robin Williams, who prepares to leave his class. The students then stage a dramatic revolt by standing on their desks. However, one of them gets too close to a ceiling fan. The result sends blood everywhere as the skit turns into a horror movie. It’s a hilariously morbid scene that involves a head being thrown around, finally being launched out of an open window. Armisen leaves after the chaos and pretends like he didn’t just watch a terrible accident happen.
#19: “Father Daughter Ad”
Dakota Johnson is an unlikely candidate for ISIS in this commercial parody. She and Taran Killam take a ride together in a sentimental setup that goes to some surprising places. The surprise ending is a darkly funny twist on the ads that try too hard to tug at the heartstrings. Johnson's casual delivery as she mentions the extremist group feels especially absurd, hammering home the irony of it all. Killam plays a proud father that tricks the audience into thinking there’s something much more wholesome happening. The final reveal takes a big swing as the daughter rides off into the sunset with the armed recruiters.
#18: “Djesus Uncrossed”
Christoph Waltz salutes his collaborator Quentin Tarantino in this parody of the latter’s filmography. Instead of doing a send-up of WWII or pre-Civil War America, this fake movie trailer spins Jesus' resurrection into a revenge plot. Waltz plays him like an action hero with one-liners galore. The skit also features plenty of over-the-top violence, turning the normally peaceful prophet into a stone-cold killer. He even uses a shotgun against Samuel L. Jackson’s Judas in a ridiculous and anachronistic touch. The actor knows exactly how to sell the writing with his trademark skills, paying homage to Tarantino's historical revisionism along the way.
#17: “Uncle Roy”
The character of Uncle Roy is not your average babysitter. Played by Buck Henry, the 45-year-old man helps out two parents that leave their girls at home. This includes playing games with them and doing magic tricks that are all intensely creepy. Throughout the sketch, it’s pretty clear that this wouldn’t fly in today’s world. Roy even starts to take pictures of the kids as they continue to misunderstand his gross intentions. When their mother returns home, she fails to see through the sitter’s happy demeanor. It’s unlikely that the program would try to revive the idea anytime soon.
#16: “Children’s Show”
Michael Keaton stars as a strange children’s show host that falls on hard times. When he receives an eviction notice, the presenter struggles to maintain his composure. His talking furniture begins to question the entire show as a result. Keaton’s Toby is found out as a fake, along with some unsettling revelations about his use of the objects in his home. A group of repo guys tries to take it all away as the program folds in on itself. Not only does the sketch offer up some dark realities about money, but it also delves into more unexpected sexual territory.
#15: “Wake Up and Smile”
A morning show loses its teleprompter in this hilarious sketch. Will Ferrell leads an anxious group of TV professionals that can’t work without a script. His team quickly loses their cool, devolving into terrified characters in a “Lord of the Flies” scenario. They eventually come back from commercial with torches lit and Ferrell taking control as the ruthless leader. This includes a tense confrontation between two presenters, ending in an over-the-top death scene. By the time the prompter returns, it’s already gone too far. The skit is completely unafraid to use graphic violence to show an extreme reaction to a fixable situation.
#14: “Totino’s”
Vanessa Bayer leads this humorous parody of food commercials in a dedicated performance. For this sketch set during a game day celebration, her character provides the group with Totino’s pizza rolls. The seemingly-robotic men chant and cheer over her dialog until a major twist happens. It turns out that the TV isn’t even on, putting into question the premise itself. It gradually turns into an episode of “The X-Files” with the sports fans revealing their true selves. Blending elements of horror and sci-fi, this skit reinvents itself in a dramatic ending that puts Bayer in jeopardy.
#13: “Chucky Lee Byrd”
In a parody of music commercials, this sketch takes a look at the work of fictional artist Chucky Lee Byrd. Will Ferrell’s rock and roll singer has a number of singles about his obsession with teenagers. The creepy lyrics keep coming until the presenters themselves start to question the content. Ferrell’s dedicated performance satirizes musicians that had questionable relationships in the 20th century. It’s a tricky subject to tackle with humor, but “Saturday Night Live” finds a way with Kate McKinnon and Beck Bennett’s commentary. McKinnon’s alarmed face and Bennett’s explanations only get better as Byrd’s problematic songs continue.
#12: “Evil Boss”
This sketch takes the idea of an angry boss to its absolute extreme. Will Ferrell plays the office manager in question, verbally and physically mistreating his underlings at every possible turn. He does all of this as a potential hire stands by, watching in horror as awful things happen. Ferrell fights one of his employees to the death in an especially brutal battle with a trident. The comedian’s nonstop fury and despicable nature makes for a darkly funny exploration of office culture. With plenty of blood, the skit doesn’t shy away from the terrible behavior of its main antagonist.
#11: “Japanese Game Show”
Chris Farley finds himself on a quiz show in Japan, but the punishment for getting things wrong ends up being worse than anyone could have imagined. He also can’t speak the language in a hilarious twist. Farley manages to squeak by on a few guesses, but his opponents don’t have the same luck. They’re forced to perform drastic surgeries on themselves. It’s the kind of shocking moment of violence that you rarely see on the show. The American contestant survives to the end, at which point he gets hooked up to an electrical torture device. Farley gives it his all in a convincing and terrified performance.
#10: “Enhancement Drug”
"SNL" is no stranger to parodying prescription drug commercials, and Dwayne "The Rock" Johnson can pretty much sell anything. So, this sketch sounds like a home run, right? This "Enhancement Drug" sketch starts off like any normal ad involving erectile dysfunction, but quickly spirals into a bevy of extreme side effects, including Johnson spouting off a random, "Hail Satan!," near the end. What's even darker, though, is how the sketch comments on the opioid epidemic. "Xentrex" isn't as dark as some of the other sketches on this list, but the implications are definitely there, for sure.
#9: “The Tizzle Wizzle Show”
The next entry on our list is short, but not so sweet. "The Tizzle Wizzle Show" is a take on your average, everyday colorful kids' show, only with a few glaring exceptions. For starters, there's knife play, unknown pills, and a fight to the death in the dark. It all starts innocently enough with a jammy dance, but things get dark REAL quick, with only guest host James Franco left standing after "The Tizzle Wizzle Show" goes horribly awry. It's the sort of black humor that permeates a lot of "SNL" Digital Shorts, with this one being absolutely no exception.
#8: “Canteen Boy”
Okay, so this sketch was ALWAYS in questionable taste, but it's even more problematic given the Boy Scouts of America’s current state. Adam Sandler's "Canteen Boy" character was a lovably dim but good-hearted assistant scoutmaster whose adventures take an incredibly dark turn alongside guest host Alec Baldwin. The scene is played for laughs, but there's nothing funny about the implied situation in which Canteen Boy finds himself, as Baldwin's supervisor pushed the boundaries of propriety beyond the pale. To be fair, Baldwin and Sandler are keen to make sure the jokes fly quickly enough to lessen this sketch's blow, but man… this is still something else.
#7: “Shark Tank”
Sometimes an audience's initial reaction tells you all you need to know about where a sketch is going. Towards the beginning of this “Shark Tank” parody, an audible gasp can be heard from the studio as the Sharks bear witness to a group of religious militants. Oh, and there's also plenty of awkward silences, as the audience can’t decide if they should laugh at this wildly dark and controversial material. Even years later, we’re not entirely sure if this is funny or if it was a bad idea right from the start.
#6: “Rosetta Stone”
"Rosetta Stone" sketch implies SO much reprehensible behavior within its scant two-minute runtime that we can barely believe it's even real. The sketch is actually a dead-on spoof of the commercials for Rosetta Stone's language-learning software, only with one supremely dark twist. There's a group of sketchy looking men all seeking to learn Thai to indulge in one of the country's most infamous stereotypes. From the sweaty, dark room web surfing, to the oversized and creepy glasses, it's a gross and button-pushing sketch that might leave some viewers picking their jaws up off the floor.
#5: “Sitcom Reboot”
Many of us are familiar with the trope of adult and child body swapping. We're talking about movies like “Freaky Friday,” “Vice Versa,” and “Like Father, Like Son.” The "Switcheroo" sketch takes things to an extreme that none of those movies touch... and probably for good reason. John Mulaney is honestly brilliant as a sitcom creator whose idea for a reboot is so troubling and offensive he's basically run out of town. His interview on "Hollywood Update" reveals that he was forced to shoot "Switcheroo" in places like Haiti and Guyana, while at the same time exposing some deep-seated childhood trauma of his own.
#4: “Family Feud”
"SNL" has had a lot of success with their game show parodies over the years. "Celebrity Jeopardy," anyone? This includes the multiple times they've tried their hand at "Celebrity Family Feud." There was something profoundly dark about this installment pitting the Osmonds against the family of John Phillips, former singer of the Mamas and the Papas. It all has to do with trauma and dysfunction as the sketch digs up skeletons from the closets of both families within the "Family Feud" framework. Jason Sudeikis does his best Richard Dawson impression, but not even his performance can stop the implications of this sketch from making our skin crawl.
#3: “Mr. Belvedere Fan Club”
Call the next sketch on our list a… product of its time. The "Mr. Belvedere Fan Club" presents a group of people whose grip on reality is tenuous at best, as they describe increasingly troubled and obsessive behavior towards their favorite fictional television character. Tom Hanks holds the sketch together as the straight man, while Chris Farley, Adam Sandler, and particularly Phil Hartman display mental health issues that would raise huge red flags today. The reactions at the time are comparatively tame, however, with the audience laughing along to the admittedly ridiculous premise in a way that undercuts how shockingly dark this sketch truly is.
#2: “Meet Your Second Wife”
This entry is a great example of a sketch that's impeccably written, but dark as hell. "Meet Your Second Wife" surprises its three male contestants by revealing to them situations whereby their otherwise happy marriages are succeeded by an increasingly young series of second spouses. The reactions of Bobby Moynihan, Taran Killam, and Kenan Thompson are brilliant, while hosts Tina Fey and Amy Poehler describe situations that honestly DO happen in real life, with a gleefully black sense of humor. The reaction shots of Aidy Bryant, Vanessa Bayer, and Leslie Jones also hammer home this sketch's perverse punch line, making this a group effort in the best/worst possible way.
#1: “World's Most Evil Invention”
Here it is, the "SNL" sketch with a punch line so dark that we dare not speak its name. Dwayne "The Rock" Johnson DID have to, however, as he portrays a mad scientist with one boundary-pushing, taboo-breaking absolutely MOST evil invention. The International Mad Scientist Society may be full of baddies, but Johnson's Doctor… um, "Roy" does them all in with a robot that's destined to be profiled on "To Catch a Predator." What's perhaps the most twisted aspect of the sketch, however, is the final reveal, when the entire thing just turns out to be an advertisement for White Castle. You truly outdid yourselves with this one, "SNL."
