5 'Saturday Night Live' Halloween Sketches For The Ages

Welcome to ComedyNerd, Cracked's daily comedy superstore. For more ComedyNerd content, and ongoing coverage of the Iran/Contra Affair, (that Oliver North's in real trouble) please sign up for the ComedyNerd newsletter below.

Sign up for the Cracked Newsletter

Get the best of Cracked sent directly to your inbox!

SIGN ME UP

Halloween on SNL is almost as fun as getting fried eggs and a lukewarm can of Miller Lite in your trick-or-treat bag. The show has created enough spook-inspired sketches over the years to fill an entire 90-minute episode and even an animated spin-off.  Throw on your pumpkin jacket and let’s go ring five decades’ worth of SNL Halloween doorbells. And Lorne Michaels' doorbell, he probably gives out full-sized Snickers.

1977: Coneheads Halloween 

This was the sixth Coneheads appearance (and for some reason, presumably drug-related, the second one was titled “Return of the Coneheads”), but the aliens hadn’t yet worn out their welcome. Sign up for a free Peacock account to hear the studio audience go nuts for another round with Beldar, Prymaat, and their daughter Connie. 

While the miserable Earth festival of Halloween is mostly a mystery, the Coneheads do their best to fit in, handing out generous helpings of fried eggs and low-cal beer. Soon, concerned neighbors ring the doorbell.  

Sharlene van Arsdale (Gilda Radner): I know your family’s just moved into the neighborhood, and I’m sorry we had to meet under these circumstances. I don’t know where you people are from, but we at Parkwood Heights do not give liquor to minors!

Carl van Arsdale (Bill Murray): Yes, we were extremely upset to find six-packs of brewski in the children’s trick-or-treat bags. 

Everyone calms down when the odd new neighbors reveal they’re from France, international home of underage drinking.  

The rest of the short sketch revolves around forbidding Connie from apple bobbing, or as it’s provocatively explained to Prymaat, submerging her cone into a fluid bath while attempting to grasp buoyant fruit with a major orifice.

1992: Adam Sandler's homemade costume ideas

While the Sandman created his share of memorable sketch characters, he did a lot of his comedy damage on the Weekend Update desk.  Declaring fancy Halloween costumes a big rip-off, Sandler demonstrates a number of DIY scary costumes that only require a face. 

Try them yourself this holiday season: Squishy Man, Crazy One-Arm Man, Crazy Hand-Coming-Out-Of-The-Neck Guy, Crazy No-Arm Woman, Crazy Spoonhead, Crazy Planthead, Crazy Plantarm.  Kevin Nealon chimes in with his own idea: Cuphead. How do they come up with these gems?

All of Sandler’s creations have one thing in common:  They want you to give them some damn candy.

The bit proved so popular (or so easy to write) that Adam followed it up in subsequent years with More Halloween Costume Ideas (Smiley Boy, About To Sneeze Man, and Crazy Newspaper Face ) and Even More Halloween Costume Ideas (Crazy Big-Eyed Man, Shaky Lip Guy, and Crazy Teabag Mouth).

1998: Jimmy Fallon on trick or treating

Holy cow, was Fallon 17 when he started on the show?  After so many years of fake laughs on The Tonight Show, it’s easy to forget Jimmy Fallon: The Bedhead Seduction Years.

Here, Fallon apes Sandler by bringing out his acoustic guitar. But instead of goofy originals about hooded sweatshirts or lunch ladies, Fallon performs a series of very 1990s song parodies with a tenuous link to trick-or-treating.  Seriously, when was the last time your heard someone break out their killer Marcy Playground impersonation?

Jimmy is undeniably charismatic here, somehow playing the guitar better than his work on the Casio keyboard for the “I Wish It Was Christmas Today” bits.

2005: Vincent Price Halloween Special

Hader’s Vincent Price was always a gas, if only because you could see how much fun he had doing it. Most SNL viewers probably aren’t old enough to recognize Price (he was a golden oldie when he did Michael Jackson’s Thriller back in 1984, for Pete’s sake), but the joke works anyway.

The black-and-white sketches (in addition to a few Halloween editions, there were also Vincent Price Christmas, Thanksgiving, and Valentines Day Specials) give the SNL cast a chance to dust off impressions of older celebs.   Guessing here that Fred Armisen wouldn’t be allowed to do his mincing, sex-hungry Liberace these days, but Kristen Wiig’s rabid Judy Garland and Jon Hamm’s gimlet-guzzling JFK are a lot of fun.

2007: Clintons' Halloween Party

Once you get past the distraction of Amy Poehler’s false Hilary Clinton nose, this sketch serves as a hilarious political snapshot of the months leading up to Obama’s first election. The Clintons throw a party with then-relevant Democratic guests including Bill Richardson, Chris Dodd, Mike Gravel, and Dennis Kucinich.  (Who, who, who, and who?) It's weird that you could be parodied on SNL one year and fall into complete political oblivion the next - so, Marjorie Taylor Greene everyone!

There are other dated pop-culture references, but Bill Clinton as Mystery from The Pick-Up Artist still gets laughs.

The sketch is famous, of course, for the big reveal -- a guest wearing an Obama mask turns out to be the real Barack Obama!  Listening to the crowd go absolutely bonkers is a good reminder of what a rock star Obama was before the realities of two Presidential terms returned him to the mortal slush pile.

2008: Will Forte trick-or-treats Jon Hamm's house 

Easily the most unsettling of all the Halloween sketches, though not in the traditional scary way.  

Will Forte scores again as yet another of his creepily off-kilter characters. At first, it’s simply disturbing to meet a grown man going door to door for candy.  Then Forte turns it up to 11 when neighbor Jon Hamm asks “What exactly is your Halloween costume?”  

“I’m a sex offender.”

There’s something about the way Hamm and Forte keep a straight-faced seriousness throughout that makes the laughs feel both uncomfortable and earned.  The goofy slate at the end is just the Charlton Chew we need to wash the bad taste out of our mouths.

2011: Shana Halloween Party

Shana at a Halloween Party - SNL

Even without Kristen Wiig’s hilarious Shana, this sketch gets points for Ben Stiller strutting around in his Planet Hollywood jacket.  For the record, “it’s not a costume.”

Shana isn’t one of Wiig’s most remembered creations, but as one-joke characters go, it’s a good joke.  The self-fondling beauty seems to be every man’s desire -- until she sloppy-chews some caramel apple, describes the undigested peanuts in her stool sample, or billows out her ghost costume with explosive, foul-smelling flatulance. 

An SNL writer trick in recent years has been to save a weak script by typing “Kenan reacts here.”  Time and time again, Thompson saves the day.  

2014: Graveyard Song

SNL has introduced a few Halloween songs to the catalog over the years, and this one starts out spooky.  Teenagers in a graveyard are threatened by a grim, scythe-wielding reaper, a twisted, rotting tree, two tombstone heads come to life, and of course ...

Paul and Phil.

Seriously, who wouldn’t want to have a Halloween party with these guys?  They can’t hold their beer--literally--but their Iowan good nature and funky dance moves turn even the most haunted forests into feel-good hangs.

2016: David S. Pumpkins

Yep, David S. Pumpkins is his definitely own thing. And the b-boy skeletons are part of it.

One of the weirder SNL breakout sketches ever, Pumpkins had a labored birth, morphing from one idea to another without finding its final-final form until air time.  

Mikey Day, Bobby Moynihan, and writer Streeter Seidell basically scribbled out a 4 am. fever dream, inspired by their love of Holiday Rap by MC Miker and DJ Sven.  The original plan was to have host Tom Hanks join the b-boy skeletons in an elaborate hip-hop routine.  There’s was only one problem, according to Hanks:

“Fellas, I don’t breakdance.“

Back to the drawing board. The name “David Pumpkins” was something Day threw out in a fit of exhaustion (Moynihan added the S.), but the writers couldn’t really figure out exactly who Pumpkins was.

“One line we almost kept, which I think is a good encapsulation of David Pumpkins,” says Day: “‘He’s not part of the known Halloween universe, but he’s acting like he is.’”

But eventually, says Moynihan, the writers realized it was simpler than that. “Nope, this guy’s weird and we’re all here on board.”

Hanks was still figuring out the character during dress rehearsal, hesitating enough to suggest that the following week’s host, Chris Hemsworth, might make an even better David Pumpkins. 

Hanks got over his trepidations, according to Mikey Day, telling them, “Gentlemen, I swear I will figure out who this David Pumpkins is by the time it’s on television.”  He did just that, breaking out the character’s distinctive voice for the first time during the live performance. 

“It’s this weird alchemy,” says Day, “of Halloween, the best host ever, the time of the country (the show was in full Trumpmania), and just a silly song. It all kind of came together.”

Hanks ended up being so pleased with the final result that he took the costume home to keep. It’s five years later and you still see Halloween celebrators young and old walking around in pumpkin-spotted sportcoats. The character was brought back for a hip-hop music video, this time as David S. Pumpkins.

Finally, the sketch was so crazy popular that Day and company turned Pumpkins into its own animated TV special.

Any questions?