Top 10 SNL Sketches That Keep Us Up at Night

Oh, how we miss you, Chris Farley. In typical Foley fashion, the highly spirited, van-dwelling motivational speaker attempts to warn some local teens about the dangers of vandalizing neighborhood houses. The teens, led by episode host Christian Slater, rather predictably don’t take Foley seriously. That is, until he asks David Spade to imagine that he’s an egg, and some incredible physical comedy ensues in Farley’s inimitable style. Foley’s victims this time around? A glass table and a giant window, the latter thanks to a bag of flaming dog poop. What we wouldn’t give for another lesson from Matt Foley…

We’ll just cut to the chase here — Andy Samberg’s character in this Digital Short is decidedly not having a great day. What appears to begin as a delightful, “Singin’ in the Rain”-esque jaunt quickly reveals itself to be something much darker and unsettling. Samberg initially seems to be an average Joe who’s simply trying to see the bright side of things. And who can’t relate to that? Well, before you answer that question, you might want to hear Samberg out. He’s a little more than just down-on-his-luck: not only have his wife and kids left the building, but not even host Alec Baldwin and musical guest Tom Petty want to hang out with him. Truly a cosmic punishment.

It’s no secret that Kristen Wiig is the originator of some of “SNL’s” most iconic characters and performances, a deeply talented impressionist who’s game for anything. And, if you’re familiar with the criminally underrated “Shana” sketches, you’ll know that we mean anything. For the uninitiated, this recurring skit finds Wiig playing the titular sexy siren, desired by every man with the great misfortune of crossing paths with her. However, as with almost any situation in which Kristen Wiig is involved, things almost immediately go awry, and Shana is definitely more than meets the eye. We’re almost more worried about Ben Stiller’s character in this sketch. Seek help, dude!

This John Mulaney-anchored sketch is downright nasty in, like, several ways. For some reason, Mulaney, Pete Davidson, and the rest of the “SNL” gang had a lot of very blue questions about the legend of Sleepy Hollow, Ichabod Crane, and in particular, the Headless Horseman. In this iteration, Crane (as played by Mulaney) is reimagined as a truly disgusting pervert who, when encountering the Horseman, isn’t even remotely scared. Rather, he floats a number of rather… innovative… possibilities as far as the, y’know, “detached head” thing goes. Where Mulaney and co. have questions for the Horseman, the audience assuredly has questions for the writers of this sketch.

One can only wonder as to the thought process that resulted in this sketch — and specifically, the existence of Peter Dinklage’s Jonathan Comets and his “space pants.” Dragged to a bar by Bobby Moynihan and Beck Bennett’s intimidating gangsters, Jon Rudnitsky and Pete Davidson are spooked into paying off their $20k debt. However, they’re saved — at least momentarily — by the hilariously incongruous Comets and his close personal friend Gwen Stefani. Why is Comets obsessed with his space pants? How does he know Stefani? We’re not even sure we want the answers to these questions!

We really wish we had Chad’s total unflappability in any given situation. Here, Pete Davidson’s most famous recurring character finds himself stranded during a road trip on a dark and stormy night, with his only option for seeking refuge being a creepy, old mansion that he almost instantly learns is haunted. Luckily for him, the haunter in question is played by Adele, as a lonely ghost who seeks Chad’s help in crossing over into the afterlife. Unsurprisingly, the well-meaning but dimwitted Chad turns out to be no help at all. Hello from the other side, indeed…

Look, before anything, we should state unequivocally that Adam Sandler’s Canteen Boy is canonically 27 years old, and continues to be active as a lifelong scout due to his relative eccentricity. Seriously, that’s from this sketch’s title card! Now, having said that, it doesn’t make this iteration, with host Alec Baldwin as a blatantly predatory scoutmaster, any less uncomfortable. Immediately controversial from the time of its airing, the sketch features Baldwin making several extremely overt attempts to come on to the sweetly innocent Canteen Boy. Thankfully, the latter has seemingly supernatural powers at his disposal, sparing himself from Baldwin’s creepy wrath.

This is one sketch where, after watching it, all you can really say is… “Well, they really went there!” You might also be asking yourself, “How did they get Dwayne Johnson to agree to this?” Well, unfortunately, we don’t have the answers to those questions, but if you find them, please don’t hesitate to let us know! Johnson plays Roy, a seemingly mild-mannered participant in the titular competition. Roy participates alongside a host of cartoonishly over-the-top comic book villains, who put forth such dastardly inventions as… a freeze ray! Once you learn what Roy has cooked up, you’ll not only be nauseous, but probably in agreement that he should take home the gold.

Remember Andy Samberg’s earlier “Great Day” sketch? Well, if you thought he was actually having a terrible day there, get ready for “The Curse,” in which the former “SNL” star seems to be in for a terrible life. It’s a tale as old as time: a callous businessman (Samberg) damages Fred Armisen’s offensive caricature’s “sacred talisman,” and in a show of pure hubris, belittles him when asked to pay up. Samberg quickly learns the error of his ways after Armisen places a curse on him… which entails a shirtless, oiled-up Jon Hamm appearing at inopportune times to play a mean jazz sax. And we mean seriously inopportune times.

Hey, they don’t necessarily have to keep you up for a bad reason! Sometimes, it’s just pure bafflement. This sketch for the ages stars Beck Bennett and Kate McKinnon as a couple in search of corny Halloween frights. What they don’t expect to find, however, is Oscar winner Tom Hanks’ now-iconic David S. Pumpkins. Pumpkins’ creepy cohorts make sense. That is, his fellow ghosts, not the inexplicable B-boy skeletons who accompany his routine… which is, what, exactly? We don’t know, but they’re definitely… part of it! While McKinnon and Bennett, despite their increasing levels of confusion, aren’t able to crack the mystery, maybe that’s for the best.

Which “SNL” sketch keeps you up at night? Let us know in the comments below! Or… maybe don’t.