With the season premiere this past weekend, Saturday Night Live celebrated its 50th season on air. It’s a remarkable achievement for a show that seemed doomed from the start (see, or maybe don’t, the historical dramedy Saturday Night, currently in US theaters) and one that has had ups and downs worthy of the Big Apple’s skyline.
Choosing the 100 greatest sketches from the show’s run would be a daunting task, so having to pick just 20 is downright impossible. For every one that is listed below, you could probably swap in 10 more just as good, if not better.
Some of these choices listed here make it in due primarily to historical significance or pop cultural relevance, but ultimately what’s the point of comedy if you must take it seriously?
Blues Brothers: Soul Man
Disregarding just about everything in the above preamble – this isn’t really a sketch and it’s not particularly funny (although it’s still a little funny) – you can’t not include this musical performance from the first breakout characters from the show: The Blues Brothers, “Joliet” Jake Blues (John Belushi) and Elwood (Dan Aykroyd). Once you get past the initial joke – these two schlubby white midwesterners have no business being this good at playing the blues – you understand what made early SNL so special: it wasn’t just funny and daring, it was cool. Original cast members Aykroyd and Belushi gave the show its first icons, which would lead to its first foray into motion pictures (with 1980s hit The Blues Brothers), and this 1978 performance, during a Carrie Fisher-hosted episode in season four, remains their most famous.
Word Association
It speaks to the transgressive brilliance of Richard Pryor and the edginess of early Saturday Night Live that this infamous sketch – in which a job interview between a hiring manager (Chevy Chase) and a janitorial applicant (host Richard Pryor) gets very tense very quickly once a game of word association turns into a volley of racial epithets – has never really been outdone. Pryor, who show creator Lorne Michaels had to fight to bring on to the program after he’d offended executives during previous live taped events, demonstrates why he’s the most ferociously funny comic of his generation, while Chase brings all of his smarminess to bear as the “honky” who comes dangerously close to becoming a “dead honky”.
King Tut
You can’t have a list of the greatest SNL anything without Steve Martin on it. And when it comes to Martin + SNL, one sketch comes first to mind: King Tut. A funky disco tribute to the ancient Egyptian pharaoh and Martin’s “favorite honky”, it’s a wonderful showcase for Martin’s skills as both a singular absurdist comedian and an immensely talented musician. Is this the most hilarious sketch ever? Not necessarily, but it’s one of the most charming.
Mister Robinson’s Neighborhood
Like Pryor before him, Eddie Murphy brought an edgy, often confrontational Black perspective to his time on SNL. But by mixing it with his megawatt charisma, he made himself into the biggest star the show ever produced (so popular was he, in fact, that he got to host while he was still a cast member). You could fill this entire list with Murphy sketches, but if you had to pick just one, you might as well go with his most popular recurring character: Mister Robinson, a gritty, inner-city version of the beloved children’s TV show host Mr Rogers. The word of the day is “bitch”.
It’s a Wonderful Life Alternate Ending
One of the premises that SNL likes to use, especially in recent years, is alternate scenes or outtakes from classic films. These are usually good for some laughs if only because we get to see the cast bust out impersonations of older movie stars. That’s the case here, with Dana Carvey – arguably the greatest impressionist in the show’s history – doing an excellent Jimmy Stewart in the beloved holiday classic It’s a Wonderful Life. But that’s not the main draw. Introduced by host William Shatner, we get treated to the film’s “lost” ending, which sees the villainous Mr Potter (who, in the real film, never gets any kind of comeuppance) beaten to death by the people of Bedford Falls. Not only does the slapstick violence of it all make for some huge belly-laughs, it also provides a measure of catharsis for fans of the film who always wanted to see Potter get his.
Unfrozen Caveman Lawyer
With the right actor, a chuckle-worthy idea can be made into an instant classic. For one of the best examples of this, see Unfrozen Caveman Lawyer, a send-up of TV legal dramas starring Keyrock, a primitive caveman from 100,000 years ago who was thawed out of the ice by scientists and decided to go to law school. It’s a funny premise, sure, but what makes it so great is the way Phil Hartman – one of the most talented and most tragic figures to ever grace the show – plays things 100% straight. That slick, mid-Atlantic voice of his, juxtaposed against his protruding facial prosthetics and wig, reading off lines such as “I’m just a caveman … your world frightens and confuses me …” before busting out the ace legalese, is a work of pure comic magic.
Matt Foley: Van Down by the River
Of all the memorable characters Chris Farley gave us during his tenure on the show, none is more beloved or more oft-quoted than Matt Foley, the high-wired, shambolic, divorced motivational speaker who subsists on a steady diet of government cheese and “LIVES IN A VAN DOWN BY THE RIVER”. The creation of Farley and Bob Odenkirk when they were both with Second City, he would appear in eight televised sketches, all of them great, but none greater than this demolition derby of a debut.
Canteen Boy: Mr Armstrong
Reactionaries often like to point to comedy of the past and say: “You could never get away with that now.” What they often don’t take into consideration is people didn’t always get away with it then, either. Look no further than this sketch, one of the most controversial in SNL’s history. In it, we find the popular Adam Sandler character Canteen Boy – a socially awkward Boy Scout obsessed with hydration (Sandler would tweak him and turn him into the title character for his later feature The Waterboy) –being aggressively groomed by his pervy Scout Master, played with comic abandon by SNL’s greatest recurring host, Alec Baldwin. So outraged were viewers that the show would dare to make light of pedophilia, that the show had to retcon the character of Canteen Boy to make him a stunted adult (which doesn’t make things much better). In DVDs containing this sketch, a disclaimer stating that factoid was included. A year later, during his next go-round as host, Baldwin poked fun at the controversy by performing a politically correct version of the sketch.
Schmitt’s Gay
Of all the fake ads SNL has ever done, none has been as brilliant in its simplicity as this one, which takes the horny, adolescent fantasy of so many beer commercials of the 90s and flips it by making it, well, gay. That the humor never comes off as mean-spirited or homophobic is partly why it works so well, but it really comes down to the clownish, boorish behavior of Sandler and Farley – both of whom would parlay those personas to great success by making movies that appealed to the same demographic this sketch is poking fun at – as they find themselves in beefcake heaven.
NPR’s Delicious Dish: Schweddy Balls
Back to Baldwin, you can’t make a list of the greatest SNL sketches without talking about this Christmas classic. Even before his character, baker Pete Schweddy, shows up to talk about his holiday confections on a radio program, the audience is cracking up at Molly Shannon and Ana Gasteyer’s pitch-perfect impressions of low-energy NPR hosts. But as soon as the trio start discussing the pleasures of his delicious “Schweddy Balls”, they’re rolling in the aisles. This is the show at its juvenile best.
Cobras & Panthers
Robert Downey Jr’s short-lived time as an SNL cast member is looked back on today as an odd footnote in his career, mostly because it came about during what’s regarded as the nadir of the show. He fared better when, in 1996, he returned to host, with this sketch being the clear standout from the episode. A parody of West Side Story, the hilarity comes not from the singing and dancing, but the bewildered reaction from the Cobra gang leader, played by the late Norm MacDonald. Rightly regarded as the greatest Weekend Update host of all-time, this sketch showcases how good he was as a sketch comedian too.
Seinfeld in Oz
One of the darkest and most out-there parodies the show ever gave us was this impressively filmed crossover between two of the most disparate television programs of the day. Fresh off the “satisfactory at best” series finale of Seinfeld, Jerry finds himself serving out his year-long incarceration in Oz, the maximum-security hellhole at the center of HBO’s prison drama. Shot on the actual Oz set with the actual cast members (who play an array of neo-Nazis, gangbangers and killers), Jerry ends up adjusting to life behind bars, reacting to all the nightmarish drama of the prison soap opera with the same “Good luck with all of THAT” nonchalance that he treated the minutiae of everyday life on the outside. Tapping into the latent sociopathy of Seinfeld’s fictional doppelganger, the comedy here is the blackest of black, and all the funnier for it.
Tales of Bill Brasky: Holiday Inn
Some of the most grotesque sketches in all of SNL, the Bill Brasky chronicles serve as a twisted version of modern-day campfire stories, only here it’s four buck-toothed salesmen getting apocalyptically sloshed at a bar and trading the most unbelievable and heinous stories about the fabled Brasky – a modern-day Paul Bunyan who stands, according to who’s talking, at “6ft 8, 340lb,” “7ft 10, 590” or “9ft 8, 790lb”. As great as all the Brasky stories are, though, the funniest moments come when the salesmen blurt out horrible truths about themselves, followed by a short moment of sober reflection – right before they go back to guzzling scotch and chewing glass.
Celebrity Jeopardy!: French Stewart, Burt Reynolds & Sean Connery
The greatest gameshow parody the show has ever done, as well as the best vehicle for celebrity impressions, Celebrity Jeopardy! was the brainchild of MacDonald and show writer Steve Higgins. It’s one thing to make fun of how hopelessly dumb celebrities are (as anyone who’s watched real Celebrity Jeopardy can attest), but the idea that in this universe, Alex Trebek (Will Ferrell) is a hopelessly put-upon everyman stuck in his own personal hell where he’s bullied by a sadistic Sean Connery (Darrell Hammond) and smirkingly sociopathic Burt Reynolds (MacDonald) is so specific in its absurdity it could only have come from Norm. Every single installment of Celebrity Jeopardy! is great, but this one makes the cut because it gave us “Turd Ferguson”.
More Cowbell
One of the most absurd and random premises in all of SNL: at a studio recording session for 70s rock group Blue Öyster Cult, their producer, the very specifically named Bruce Dickinson (Iron Maiden fans have tried for years to figure out why he was named after that group’s lead singer), played by one of SNL’s all-time great hosts, Christopher Walken, interrupts and demands – what else? – “more cowbell”. The only thing more impressive than how well it all comes together is how popular it would go on to be. There’s an argument to be made that this might be the single most beloved sketch in the show’s history.
Woodrow: Britney Spears
As with others before him, Tracy Morgan has almost too many incredible sketches and characters to choose from. And while his simple-minded animal trainer Brian Fellows is probably his most iconic, I’ve always been partial to Woodrow, his sweet-natured, but dangerously schizophrenic homeless man. Of all the Woodrow sketches, this one, starring Britney Spears at the height of her popularity, is by far the best, partly because it’s legitimately sweet, but mostly because we get to hear the biggest pop princess of our time sing “Make a doo-doo pie” alongside Morgan.
CBS Evening News: Katie Couric Interviews Sarah Palin
Looking back on this cold open from 2008, it proves to be a Rubicon moment for both American politics and Saturday Night Live’s way of approaching them. If it weren’t for the meteoric rise of Sarah Palin during that election, would Donald Trump have been able to succeed where she failed? And if it weren’t for how big of a hit this mockery of her was – Tina Fey, who had left the show by that point, bore so much of a resemblance to the would-be VP that there was never a question of her not returning – would the show have gone down the path of political stunt casting, reaching out to former cast members and celebrities to play the big-name politicos, instead of using player from their own bench? Regardless, this cold open remains one of the greatest of all time, not least of all because much of the dialog is taken verbatim from Palin’s disastrous interview with Couric.
Spelling Bee
The simplest, stupidest of sketches, which makes it one of the funniest. Watching Will Forte’s nervous middle schooler run through the entire alphabet (out of order) for over a minute while trying to spell the word “business”, we’re right there with the live studio audience as their patience begins to dip, only for them (and us) to come roaring back the longer it goes on. Forte’s dead-eyed, soft-spoken performance is an all-timer, but almost as good is Chris Parnell’s deadpan moderator, especially when, at the end of it, he simply utters, “Wrong.” The Tenacious D (RIP) performance that caps everything off is the cherry on top.
Meet Your Second Wife
When Fey and Amy Poehler shared co-hosting duties in 2015, they gave us one of the most brutal send-ups of modern sexual politics and gender dynamics the show had ever seen by way of the gameshow Meet Your Second Wife. Three male contestants, all of them happily married with their wives cheering them on in the audience, are introduced to their future betrothed, girls whose current ages range from preteen to prenatal. The darkly hilarious premise is further bolstered by the horrified reactions from the contestants and their spouses.
Totino’s with Kristen Stewart
Honestly, the entire Totino’s trilogy deserves ranking here. As the nameless, thankless housewife whose entire existence centers around feeding miniature pizza rolls to her “hungry guys” during the “big game”, Vanessa Bayer crafts one of the most unsettling characters in recent memory. More than just parodies of bro-y snack ads that infantilize women, she digs deep into the meta-muck of it all to create a lost soul trapped in a suburban version of hell. But in the final entry, she is freed by the love of Kristen Stewart’s seductive stranger, with the two embarking on an erotic journey straight out of a Palme d’Or-winning French drama.
Career Day
In recent years, Adam Driver has become one of the most highly anticipated returning hosts, and for good reason. His willingness to get weird was already apparent from the movies he’s made, but, boy, does he let his freak flag fly on SNL. Although his reprisal of his Star Wars villain Kylo Ren in an episode of Undercover Boss is his most popular sketch to date, I’m fonder of this gonzo one from 2018. In it, he plays Abraham H Parnassus, the aged, decrepit father of a middle school student come to speak to his class during career day. His occupation? “For 82 years, I’ve been an oil man.” He then proceeds to go full-blown powder keg, stabbing a dead crow with his cane while giving a furious Darwinian speech about crushing one’s enemies. By the end, the rest of the cast is laughing as hard as the audience, and you can hardly blame them.
