The 20 best Halloween TV specials – from ‘Friends’ to ‘Curb Your Enthusiasm’

One-off frights fit for a Halloween binge sesh

TV loves a holiday special. Whether it’s the classic Friends Thanksgiving spectacular or a Community Christmas gift, a themed special has been a staple of television for decades, a comforting reminder that those on the box are just like us.

And Halloween is no different. From the delicious delights of the long-running Treehouse of Horror Simpsons specials to a Larry David one-off, spooky season has proven to be ripe material for TV writers, particular on the sitcom side of things.

‘Curb Your Enthusiasm’ Halloween special ‘Trick or Treat’. CREDIT: HBO

Curb Your Enthusiasm – ‘Trick or Treat’ (2001)

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Where to stream: NOW

Larry David was born to pick apart the societal weirdness of trick or treating. Those that love a Larry rant are treated to one of the best as he takes aim at pesky sweet hunters he thinks are gaming the unwritten rules and regulations. Wearing clothes that are too normal? Get lost. Too old for trick or treating? Don’t count on a Hershey bar.

Bob’s Burgers – ‘Tina and the Real Ghost’ (2014)

Where to stream: Disney+

TV’s most emotionally mature animated sitcom proved it had a really great understanding of its characters as it explored the forlorn Tina and her love life in the form of Jeff who turns out to not really exist. Those with particularly strong hearing, see if you can catch Bubbles from The Wire as a pest exterminator.

Friends – ‘The One with the Halloween Party’ (2001)

Where to stream: Netflix

Somehow the only Friends Halloween special. This more than makes up for it by giving us a Sean Penn guest spot in which he dresses up as the solar system, a Phoebe and Ursula love triangle and Ross as Sputnik but looking like a potato with a colander on its head. Matt LeBlanc does a Chandler impression and it is remarkable.

New Girl – ‘Keaton’ (2013)

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Where to stream: Disney+

New Girl had its fair share of good Halloween specials but it’s Keaton that steals it as it turns out Schimdt has based his entire life around the fact he is pen pals with Batman and Beetlejuice himself. And yes, Zooey Deschnael does a Batman impression.

The Simpsons – ‘Treehouse of Horror V’ (1994)

Where to stream: Disney+

The Shinning. James Earl Jones as Maggie. Principle Skinner eating poor Uter. The fifth Simpsons Halloween special is a tornado of gags and references that range everywhere from Dostoyevsky to Terminator 2. The incredibly detailed parody of Stanley Kubrick’s The Shining still stands as one of the greatest spoofs of all time.

Halloween TV
‘The SImpsons’ Halloween special ‘Treehouse Of Horror V’. CREDIT: Fox

Family Guy – ‘Halloween on Spooner Street’ (2010)

Where to stream: Disney+

Only in Family Guy could a basic premise such as Brian taking Stewie trick or treating (dressed as a duck) turn into a smorgasbord of squeamish gags involving Peter getting a kamikaze attack confused with the Culture Club hit ‘Karma Chameleon’. An episode for the hardcore.

Frasier – ‘Halloween’ (1997)

Where to stream: All4

Oh those Crane boys love their Halloween especially when Niles hosts a party in which all the guests have to come as their favourite literary character. Frasier dresses up as Geoffrey Chaucer while Niles hosts as Cyrano de Bergerac complete with the fake nose to end all fake noses.

Two and a Half Men – ‘Hi, Mr Horned One’ (2005)

Where to stream: Prime Video

Before the show and its star fell off, Two And A Half Men was a fun and neurotic look at middle-aged anxiety with this Halloween special being a particularly humorous look at an old scoundrel willingly entering a curse just to be with a younger woman. Holland Taylor as the Wicked Witch is particularly cackle-worthy.

It’s Always Sunny In Philadelphia – ‘Who Got Dee Pregnant?’ (2010)

Where to stream: Netflix

An old school ‘who’s the daddy?’ mystery gets a suitably Sunny twist with it being insinuated that one of the gang got Dee pregnant. Though the answer is revealed several episodes later (Mac’s trans ex-lover Carmen) the real delight is the alcohol impaired Rashomon-like structure with Dee at one point confused with an ostrich.

Freaks and Geeks – ‘Tricks or Treats’ (1999)

Where to stream: not currently available in the UK

The cult classic one-season wonder could only manage one Halloween episode but it’s a cracker as Lindsay and the freaks get swept up in a whirlwind of vandalisation across Detroit while wearing some deliberately lame costumes. An early glimpse of Linda Cardellini’s star.

Freaks and Geeks
‘Freaks and Geeks’ Halloween special. CREDIT: Alamy

Gossip Girl – ‘How to Succeed in Bassness’ (2009)

Where to stream: BBC iPlayer

The wealthy beyond all conceivable reality characters of Gossip Girl never needed an excuse to dress up but its holiday episodes always took it to the next level. Here, the guys get dolled up as 1920’s gangsters and look more boyish than Bugsy Malone. The girls, including a pre-Ryan Reynolds Blake Lively pull off their flapper wear more convincingly.

The League – ‘Ghost Monkey’ (2010)

Where to stream: Apple TV+

All of the characters in The League are adults masquerading as children but no more so on Halloween when they realise suburban houses and kids mean you can’t have exactly the same kind of fun you used to. They decide to have one last blow out with a soon to be deceased monkey, a Kesha-heavy playlist and a girl scout on ecstasy.

Buffy The Vampire Slayer – ‘Halloween’ (1997)

Where to stream: Disney+

You can’t have a vampire show without a Halloween episode, especially one as self aware as Buffy. In a neat twist, the inhabitants of Sunnydale get turned into their costumes with Willow stealing the show after her sheet-over-the-head outfit transforms her into an actually invisible ghost. The best of Buffy.

Cheers – ‘Fairy Tales Can Come True’ (1984)

Where to stream: Paramount+

Cheers was also good for a seasonal episode but it’s very first Halloween special – in season three – eschewed the scares in favour of sentimentality. Despite featuring a reading of Edgar Allen Poe poem The Raven and Kelsey Grammar dressed as the Mad Hatter, the episode actually belongs to John Ratzenberger’s Cliff who bags a date and a slow dance with Tinker Bell.

The Cleveland Show – ‘It’s the Great Pancake, Cleveland Brown’ (2010)

Where to stream: Disney+

Capturing the timeless awkwardness of being too old to do the things you loved as a child, this Cleveland Show special sees Cleveland Jr ignore societal norms and go trick or treating dressed as a pancake. Stay for the kid singing ‘Closer’ by Nine Inch Nails at the Halloween party.

Halloween TV
‘Malcolm In The Middle’ Halloween special. CREDIT: Alamy

Malcolm In The Middle – ‘Halloween’ (2005)

Where to stream: Disney+

Before Bryan Cranston broke bad, he had a paralysing fear of ghosts on Malcolm In The Middle. The neurotic dad of five starts going insane at the thought of living in a house where a murder occurred while his sons (wearing some very lazy costumes) continue to terrorise the neighbourhood and get into an egg-throwing war with an elderly neighbour. Old school mischief from an old school sitcom.

South Park – ‘Hell on Earth 2006’ (2006)

Where to stream: Paramount+

A surreal later entry for South Park that somehow manages to riff on My Super Sweet 16, Candyman and the death of Steve Irwin. Satan is planning the Halloween bash to end all Halloween bashes which gets attended by the former crocodile hunter complete with stingray protruding out of his chest. He then gets kicked out for not wearing a costume. Don’t laugh…

I May Destroy You – ‘Social Media is a Great Way to Connect’ (2020)

Where to stream: BBC iPlayer

Not your standard Halloween episode. Michael Coel’s masterpiece features Halloween with a twist as Arabella puts on a costume fit for the Paris runway before tensions ignite over the subject of sex and consent.

Community – ‘Epidemiology’ (2010)

In terms of TV Halloween costumes, Joel McHale as David Beckham but not even bothering with a football kit, has to be up there with the best ever. The gang attend a party that’s only playing ABBA songs and campus has a Walking Dead-style zombie panic after an infection spreads. Having to thermostat at the right degree stops the disease transmitting – if only that was true in real life.

This Is Us – ‘The 20’s’ (2017)

Where to stream: Disney+

A flashback episode and Halloween special all in one that seems to garner unintended laughs courtesy of the fact a bunch of 40-year-old actors are dressed to look down with the kids. US network TV’s favourite drama proved there’s one thing scarier than the ghosts and ghouls and goblins – your 20’s.

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