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Saturday Night Live

50 Best Saturday Night Live! Sketches of All Time

Papyrus! Cowbell! Head Wound Harry! They're all here—plus quite a few that you wouldn't expect.

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What constitutes a great Saturday Night Live! sketch? The question is more complicated than it seems. Besides the obvious issue of subjectivity—I’m sorry, but I just don’t think "Opera Man" is funny—there are several SNL-specific issues we have to think through before we pick favorites. For instance, what’s the difference between great characters and great sketches, or are they synonymous? I love Tracy Morgan’s lip-glossed embodiment of the idiosyncratic zookeeper, Brian Fellows, as well as Will Ferrell and Cheri Oteri’s Spartan cheerleaders. But did either of those characters produce one of SNL’s best sketches? I’m not so sure.

And what about "Weekend Update" desk segments? Do those count as sketches? Well, as an official member of Esquire’s divisive Pete Davidson fan club, it's my duty to include them. Also, I've decided to include digital shorts, commercials, and all things pre-taped because. If I didn’t, this list would end in 2003 and Esquire would call it "50 Times Eddie Murphy and Will Ferrell were Hilarious on Live Television on Saturday Night." Finally, are cold opens sketches? Sure, why the hell not? Now that we’ve determined what a sketch is, let’s establish what makes one exceptional. To be clear, funniness is not the only factor that matters. Legacy counts, too. How well has the sketch held up over time? Do people still quote it? What about its impact? Did it change the culture of the show? The culture of America? The way we view a certain celebrity or politician? Here’s the other criteria I came up with:

Originality: The more out there a sketch is, the better. Translated: less reliance on game-show formats. The obvious exception is every "Celebrity Jeopardy" sketch ever.

Breaking: Everybody loves it when cast members break out laughing during a sketch. But just because Jimmy Fallon can’t keep his shit together doesn’t mean it’s a quality sketch. This is a serious list, which means sketches that produced cheap laughs from mishaps, cast mistakes, or Christopher Walken’s insane way of reading cue cards, will be limited.

So let’s get on with the reason we are all gathered here today: Esquire’s definitive list of the 50 Best SNL sketches of all time. It's the “Matt Foley Motivational Speaker” of Best SNL Sketches listicles, if you will. And if you’ve got a problem with that reference, I look forward to not reading the opinion you shared with me in the comments section.

50

Mary Katherine Gallagher Wants To Join A Gang

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Youths of the nation take note: this is what it looks like to commit to the bit.

49

White Like Me

Ever wonder where the idea for the underrated comedy White Chicks came from? Look no further than this 1984 pre-taped sketch from Eddie Murphy. Styled like a mock investigative documentary, “White Like Me” sees Eddie Murphy going undercover as a white person for a day—and discovering that everything is better when you’re white.

48

Black Jeopardy with Tom Hanks

Michael Che and Bryan Tucker, the two writers behind "Black Jeopardy," knew they had to deliver a great sketch for legendary host Tom Hanks. Thankfully, they didn’t disappoint with this 2016 election-inspired bit. As the Trump-loving Doug, Hanks unexpectedly bonds with his fellow Black contestants over their shared grievances and manages to nail all the questions that the white contestants usually get wrong. The sketch was a huge hit at the time, with Oprah even calling Hanks to tell her how much she liked it.

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47

James Brown Celebrity Hot Tub Party

Many of Eddie Murphy’s best impressions relied on inversion. Gumby reimagined as an asshole, Mr. Rogers if he were homeless, etc. But in this legendary sketch, Murphy delivers a straightforward impression of James Brown—because sometimes the source material is so ludicrous, it shouldn’t be messed with. If James Brown ever vamped about getting in a hot tub in real life (and he probably did), this is what it looked like. I also suspect this sketch was the inspiration for Kenan Thompson’s iconic “What’s Up with That?” performances.

46

Spelling Bee

To enjoy this dark horse of an SNL sketch, you have to really like Will Forte, whose absurdist sense of humor isn’t everybody’s cup of tea. But even if you can’t find the joke in this sketch about a man who seriously misspells the word “business” (hint: there isn’t one), you should at least be able to appreciate Forte’s commitment. It’s funny because it’s ridiculous.

45

Totino's with Kristen Stewart

In an interview with Vulture, former SNL writers and The Other Two co-creators Chris Kelly and Sarah Schneider revealed that the inspiration behind their string of Totino's commercials was how funny cast member Vanessa Bayer was when she was sad. “Smiling through pain is Vanessa Bayer’s sweet spot,” Kelly said. The Totino's commercials were an annual tradition for a while, appearing every year around the time of the Super Bowl, with Bayer playing the titular role of a desperate, dejected housewife who just wants to feed her “hungry guys.” But things begin looking up for Bayer in the final installment of the series, when Kristen Stewart—hot off the heels of her official coming-out—finally gives Bayer the attention she craves. “I’ve never had one” should go down in history as the funniest response to the question: “What’s your name?”

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44

The French Chef

When it comes to gory sketches about food prep starring Dan Akroyd, most people will point to the legendary “Bass-o-Matic” as the obvious, if not only, choice. But early SNL got a kick out of disgusting, kitchen-themed sketches, and the lesser-known "French Chef" sketch is simply funnier than the infamous blender infomercial. Akroyd’s impression of an injured and bloody Julia Child trying to fasten a tourniquet out of an old cheesecloth and a chicken bone is a pure *chef’s kiss* moment.

43

Jeffrey's with Sean Hayes

"Jeffrey’s" was a recurring sketch from the early ‘00s about snooty department store employees. It was based on a real store in New York City...and the owner wasn’t thrilled about the sketch. But even he had to admit that this installment with Sean Hayes, which instantly became a fan-favorite, was good for business, telling The Advocate in 2008, “All my friends thought it was the most incredible, wonderful thing in the whole world and that I should be thrilled.”

42

Two Wild and Crazy Guys: Computer Dates

The Czech-born Festrunk Brothers, AKA two wild and crazy guys, were some of SNL’s first beloved staple characters. Plus, they're the clear inspiration for Chris Kattan and Will Ferrell’s Roxbury guys two decades later. First introduced in the season 3 premiere in 1977, these Soviet Union refugees (played by Akroyd and Steve Martin) constantly strike out with women, thanks to their heavy-handed but harmless approach. In this sketch, the perpetually cool Garret Morris, SNL’s first Black cast member, tries to explain to the perpetually overconfident nimrods that they’ve been stood up by the supermodels they’re expecting. The joke, though, is on Morris. The supermodels, AKA Gilda Radner and Jane Curtain, actually show up—and, for once, the creepy guys get the girls. The sketch was a huge hit when it first aired, but nearly 50 years later, what remains funny aren’t the dated jokes about romance. It’s the giant portable vacuum with the Czech word “Pozor!” on it. (Translated: "Warning!") That’s a Cold War relic if I ever saw one, and more evidence that SNL’s prop department is the secret ingredient to the show’s longstanding success.

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41

Colonel Angus

Many of SNL’s head writers have been major word nerds, and as such, they love a joke based on pronunciation. Take, for example, 2003's Tina Fey-written sketch about a Colonel visiting women at “Shady Thicket” grove and the many women who are, well…excited …to greet him. Say the name of this sketch out loud in a Gone with the Wind-style Southern accent, and you’ll immediately understand the premise.

40

NPR’s Delicious Dish: Schweddy Balls

For as many iconic cultural moments SNL has produced, very few of them have been tied to the holidays. Name a famous holiday-themed SNL sketch other than Adam Sandler’s "The Chanukah Song." If you thought of anything, it was the Schweddy Balls sketch. Sure, all the double entendres are funny, but it’s really Ana Gesteyer and Molly Shannon’s spot-on impressions of quaint NPR hosts that get me.

39

Meet Your Second Wife

You know how whenever you hear about a couple with a crazy age gap, you can’t help but think, She wasn’t even born when he was 20! This is the exact thought that sprung to life, and it is so disturbing.

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38

Super Showcase Spokesmodels Sketch

Now class, what did we learn from the "Super Showcase Spokesmodels" sketch? That’s correct: that Studio 6H’s soundstages are too small for a golf cart.

37

Close Encounter

No one plays a weirdo like Kate McKinnon. Writers Mikey Day and Streeter Seidell created the perfect role for her in this sketch, which is about three people who were abducted by aliens and the one lady (McKinnon) whose experience isn’t like the others. What made everyone on stage break? Probably McKinnon’s impression of the aliens “gently batting” around her knockers.

36

CBS Evening News: Katie Couric Interviews Sarah Palin

All of Tina Fey’s Sarah Palin sketches are now legendary, but this one deserves special recognition due to how closely it resembles its source material. Watch the interview this sketch is attempting to satirize, and you’ll appreciate how little Fey and Couric are actually doing here. Restraint doesn’t come naturally to sketch comedians.

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35

Star Wars Undercover Boss: Starkiller Base

The premise of this digital short—the evil Star Wars character Kylo Ren is upset that his underlings on the Starkiller Base don’t like him—is so absurd that all Adam Driver had to do to make it successful was be his usual super-intense self. Thankfully, he did just that—and the sketch was a hit.

34

Evil Boss

It’s so hard to pick a favorite “Will Ferrell flying off the handle” sketch because there are so damn many of them. The curly-haired Californian excelled at playing characters with anger issues. Many of his most beloved sketches—“Evil Boss,” “Dysfunctional Family Dinner,” “Dissing Your Dog”—feature the same character, just in different clothing and seething at different volumes. In “Evil Boss,” Ferrell goes full-throttle. Honestly, watching him act completely unhinged in a sketch that would not be allowed on air today is exhilarating. But if you prefer your Ferrell freakouts a little more mellow, maybe watch “Dysfunctional Family Dinner” and work your way up to “Evil Boss.”

33

Weekend Update: Stefon on Halloween's Hottest Tips

Stefon, the legendary nightlife correspondent of "Weekend Update," was less of a character and more of a cruel joke on Bill Hader. Every week, John Mulaney, who wrote the Steffon segments with Hader, would change the lines at the last minute, amping up the ridiculousness to try and get Hader to break. Watch this sketch closely and you’ll see Hader staring at the cue cards in disbelief over what he is about to say. That’s why Hader always tents his mouth, too. It’s not a character quirk he came up with for Stefon. Really, he’s trying not to visibly lose it before (in this sketch) explaining that a human pinata is, “that thing when a Mexican midget eats a lot of candy and then dances until he throws up.”

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32

Beavis and Butthead

I know, I know. Including a sketch from the most recent SNL season on a “Best of” list is ballsy. Not enough time has passed to properly consider its legacy! But this simple, borderline stupid sketch, in which two audience members are unaware of their striking resemblance to the animated TV show characters Beavis and Butthead, has already racked up 17 million views on YouTube. It’s also the funniest live sketch SNL has produced in at least five years. It’s not because Heidi Gardner breaks not once, but twice after turning around to see Mikey Day dressed as Butthead, exposed gums and all. Performers breaking isn’t inherently funny! What’s hilarious is Mikey Day staying in character as a clueless Butthead-lookalike, responding to Gardner’s comment about his distracting looks with a dumbfounded expression and: “I’m sorry, me?” Yes, you!

31

Brenda the Waitress

"Brenda the Waitress" is an incredible sketch that isn’t so much funny as it is…sexy. Alec Baldwin and cast member Jan Hooks play a mysterious cowboy and a waitress whose flirty back and forth about pie ends in bizarre heartbreak. There’s so much chemistry between these two in this sketch that you’ll wonder what went on at the cast party later that evening.

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