The 10 Most Hilarious Halloween TV Episodes

Alistair Gray
TV Horror
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Outside of the likes of American Horror Story, horror doesn’t translate too well to episodic TV, so television prefers to play Halloween for laughs. It’s a ripe comedic set-up: costumes, candy and competitive egos always offer the potential for laughs, but often it’s the enforced fun aspect of Halloween that provided satisfying humour — it’s a season that’s endured through gritted teeth as much as it’s enjoyed. Join us as we look at TV’s 10 greatest examples of hilarious Halloween hijinks! (Participation is not optional; anyone not having fun will be deemed a buzzkill and excluded from all future events as a social pariah).

The Office – “Halloween”

Season 2, Episode 5

The Office
Michael Scott figures that two heads are better than one

Dunder Mifflin comes alive at Halloween — because mandatory fancy dress and an excuse to goof off sounds something like Michael Scott’s perfect day at work. Unfortunately there’s serious business at hand, as Michael needs to fire someone by the end of the day. With echoes of the dismissal of David Brent while dressed an an ostrich jockey, Michael eventually lets no-mark Devon go, who is dressed — fittingly — as a hobo. There are other equally great Halloween episodes of The Office – Creed’s showstopping cosplay of The Joker comes to mind — but none capture the formula of the show’s success quite as succinctly: the idea that business and pleasure can’t mix, no matter how hard Michael wishes it were true.

Community – “Epidemiology”

Season 2, Episode 6

Troy and Abed get their cosplay on

Leave it to Dean Pelton to turn something as straightforward as a Halloween party into a flesh-eating zombie apocalypse. The students of Greendale turn rabid at their Halloween rager thanks to an airborne virus caused by cheap “military meat,” and the fun and flirtations quickly descend into a Romero-esque fight for survival. There’s competitiveness in the air even before the zombification begins: Jeff (dressed as David Beckham i.e. holding a football) and Troy (dressed as a Sexy Dracula i.e. shirtless) compete to see who can care the least about their costumes. It matters not: Abed’s Xenomorph outfit is damn near unbeatable anyways.

How I Met Your Mother – “The Slutty Pumpkin”

Season 1, Episode 6

How I Met Your Mother
'The Barnacle' in action

An early episode of HIMYM — before Ted’s romantic quest became entirely intolerable — “The Slutty Pumpkin” is a fine example of the pitch perfect comedic interplay between Ted and Barney. One is a hopeless romantic, the other a shameless pig, and the set-up that sees Barney dressed in a devil costume whispering wicked thoughts into Ted’s ear while a stoned Angel does the opposite is inspired. Ted’s fruitless mission to locate a girl dressed as a “slutty pumpkin” he met four years ago sees him wearing the same outfit in case she recognises him — a “hanging chad” costume based on the infamous 2000 Florida election recount. It’s a neat touch in an episode full of great costume gags.

Modern Family – “Open House of Horrors”

Season 4, Episode 5

Modern Family
Do not mess with a pregnant Colombian woman on Halloween

“You put an egg on my house, I kill what you love!” The shrill screams of Gloria still ring in our ears every Halloween, but although she isn’t that keen on the antics of October 31st, the rest of the Dunphys are still majorly into fright night. However, after scaring children half to death in the Season 2 Halloween episode, Claire has been told by the neighbourhood she has to tone down the terror (Phil: “You’re the type of person who can be twice as scary without makeup!”) while Cam and Mitchell suffer minor drama when a mis-sized costume means nobody can see the results of Cam’s weight loss. The episode belongs to Gloria, however, whose pregnancy hormones make her more irrational — and more genuinely threatening — than ever.

The Simpsons – “Treehouse of Horror V”

Season 6, Episode 6

The Simpsons
No TV and no beer make Homer... something something

This entire list could be comprised of Treehouses of Horror, but if we have to pick just one, it’d be this Season 6 three-part spectacular. “The Shinning” is a perfect Kubrick parody, complete with an all-time greatest Homer line-reading (“Go crazy?” “Don’t mind if I do…”) and a touch of axe-related ultra-violence for good measure; “Time and Punishment” is a unique Simpsons spin on the consequences of time travel which ends with Homer punching as many dinosaurs as he can; final segment “Nightmare Cafeteria” is a genuinely frightening tale about how your teachers really just want to eat you. And then it ends with the fog that turns people inside out, and a show tune. A perfect episode of television.

Friends – “The One With The Halloween Party”

Season 8, Episode 6

Chandler's sex face in full effect

You haven’t known true Halloween horror until you’ve seen Chandler’s sex face. This classic Friends episode is all about the costumes. On one hand, you’ve got Ross dressed as potato-based satellite “Spudnik” arm-wrestling Chandler dressed as the Easter Bunny (“Suddenly I don’t have the worst costume any more”). Then we have a pregnant Rachel (“I am a woman who spent a lot of money on a dress because pretty soon, she won’t be able to fit into it”) picking fights with local candy-napping kids. The best costume at the party, however, goes to Joey, who turns up wearing the most boring-looking sweater vest imaginable: “I’m Chandler! Blarrghhh!” Game, set and match.

Curb Your Enthusiasm – “Trick or Treat”

Season 2, Episode 3

Curb Your Enthusiasm
This is how Larry's face always looks when his doorbell rings, to be fair

Oh Larry. If the Seinfeld creator would only play by society’s rules, he wouldn’t get in half as much trouble. Everyone knows you always give trick-or-treaters candy, but Larry decides his Halloween visitors didn’t put enough effort into their costumes, so opts for ‘trick’ — which duly arrives, in the form of a barrage of eggs and toilet paper. Oh, and the words “BALD ASSHOLE” spray-painted on his front door (“That’s a hate crime!” yells a frustrated Larry. “We consider ourselves to be a group!”). He breaks yet more boundaries later in the episode, when he manages to insult a man in a wheelchair, and is labelled a self-hating Jew for whistling Wagner: “I do hate myself, but it has nothing to do with being Jewish!” All in a day’s work for Larry David.

Frasier – “Halloween”

Season 5, Episode 3

The Cranes celebrate Halloween the only way they know how: pretentiously

“Not now Niles, this pointy hat is a babe magnet!” Frasier is a show that’s built on absurdity, so it’s tailor made for Halloween, an evening that only compounds the tangled romantic lives of the Cranes and their kin. Through various misunderstandings and overheard conversations, Niles becomes convinced that his beloved Daphne has fallen pregnant — and that Frasier is the father. After all sorts of kerfuffle — everyone is dressed as famous literary characters, which makes the whole mix-up seem even more pompous than usual — we discover that it is actually Roz who is with child, but not before all involved have revealed their personalities way better than any costume choice ever could.

It’s Always Sunny In Philadelphia – “Who Got Dee Pregnant?”

Season 6, Episode 7

It's Always Sunny in Philadelphia
"Shut up, bird!"

One of the best episodes of Always Sunny full stop, “Who Got Dee Pregnant?” is as smart and funny an episode of comedy as you’re likely to see — all without losing its near-the-knuckle gags and nasty streak. When Dee reveals she’s pregnant and that *dun-dun-dunnn* one of the gang is the father, Charlie, Mac and Dennis all have flashbacks to the drunken night in question, to discover whether any of them truly could manage the worst thing imaginable — doing the dirty with Dee. It’s like Rashomon, if all of the characters in Rashomon were the absolute worst people alive.

Brooklyn Nine-Nine – “HalloVeen”

Season 5, Episode 4

Brooklyn Nine-Nine
Happy HalloVeen, everyone!

The Nine-Nine‘s Halloween heist episodes are always season highlights, as the members of the precinct stage annual competitions to outsmart one another, but Season 5’s heist stole the most valuable thing of all: our hearts. The shenanigans are as ridiculous as ever, involving a stolen belt, handcuffs, a corgi, a decoy corgi and a Handmaid’s Tale-inspired flashmob, but the greatest feat of misdirection in the episode is the one pulled by Jake, who hijacks proceedings to propose to co-worker and long-term girlfriend Amy. It’s a great romantic rug-pull, in keeping with the uplifting TV of showrunner Michael Schur, but “HalloVeen” is never less than hilarious with it.

Alistair Gray
Blogger, writer, general word-make-gooder. I will proofread your article even if you don't want me to.