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The 15 Best Halloween TV Specials!

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With the spookiest season of the year right around the corner, we look at some of the best times Halloween invaded TV
in spite of it ultimately coming down to marketing and advertising dollars in the end, I still like it when television shows indulge in holidays. Shows like Friends could even help make a name for themselves by tapping into the perfect holiday and making it a yearly tradition. Christmas specials have been a long-standing tradition and no doubt see the most attention, but Halloween has done a respectable job at getting up there and becoming a nearly as popular staple for TV to give in to. With Halloween’s arrival this year being imminent, we thought we would dig into some of the best Halloween episodes of television! Here’s your new binge list!


Psychoville
“Halloween Special”

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This British acid trip might not be on your radar, but it’s the show that I think of when it comes to Halloween and it’s produced the prototypical Halloween special as far as I’m concerned. The main reason this episode (which is brilliantly a collection of short stories, while also a hugely canonical installment that bridges the show’s first and second seasons) resonates so much is because show creators, Reece Shearsmith and Steve Pemberton, are tremendous horror junkies. Their show to begin with is a huge love letter to the genre and so while most British series turn out an Xmas special there’s a certain poetic justice that instead Psychoville would turn out a Halloween one. Christmas means nothing to them. All Hallow’s Eve is their holy day. Messed up stories that include ruminations on The Ring, An American Werewolf in London, and The Eye fill the episode, while simultaneously accumulating a rather large (lasting) body count for a comedy series. Seek out this show and this special and add some flavor to your holiday!


The Simpsons
“Treehouse of Horror V and XIV”

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The Simpsons is a no brainer here. The show loves Halloween so thoroughly that they’ve made their “Treehouse of Horror” segments a yearly fixture in the show for 28 seasons (that’s a total of 84 segments total, for those doing the ghoulish math). Due to the sheer wealth here, and certain Treehouse of Horrors from the show’s golden years seem like the obvious answer, I’ve included both an entry from the show’s early years as well as from its later half (and if ya’ don’t like it you can take it up with Halloween List Court). “Treehouse of Horror V” is pretty flawless Simpsons. The three segments, “The Shinning”, “Time and Punishment”, and “Nightmare Cafeteria,” are all efficient missiles of comedy. “Time and Punishment” is such a tight, wonderful entry and “The Shinning” is as strong as parody gets.

Then, from season 15, “Treehouse of Horror XIV” has a surprising amount of merits to it for later Simpsons. Here, the stories, “Reaper Madness”, “Frinkenstein” and, “Stop the World, I Want to Goof Off,” all hit different heights of humor. Homer as the Grim Reaper has a lot of value to it (as does him recalling his stint as Death in another segment). “Frinkenstein” brilliantly casts Jerry Lewis as Professor Frink’s father, and the latter is just fun, frantic visual gags.


Curb Your Enthusiasm
“Trick or Treat”

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“Trick or Treat” is a strong example of early Curb Your Enthusiasm that operates on all cylinders and comes together in sublime fashion. Unsurprisingly Larry fails to give some costumeless Halloweeners any candy, and he finds his house ending up the recipient of some vandalism. In perfect Larry David-like fashion, he breaks down the phrase “trick or treat” to an extreme degree and trying to use it as means to get these kids thrown away. Plus, there’s the glorious analysis as to whether “Bald Asshole” qualifies as a hate crime or not, and what sort of rights bald people actually have. As one might suspect from Curb, there’s plenty of other disparate plot lines bumping around in this episode involving things like an anniversary, a cobb salad, and Wagner music, but it’s Larry’s battle with the vandals that’s the element that revolves around Halloween.


Happy Endings
“Spooky Endings”

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Most people have clued in towards the brilliance of Happy Endings at this point (although perhaps a little too late for the show’s own good), but at the least you can honor the show during the Halloween season with a tremendously funny episode from its too-short run. The majority of the gang ends up at a warehouse Halloween party where everyone’s biggest concerns are their costumes, which have failed to make an impression yet. Getting an episode that’s mostly all about the stress and disappointment of costuming on Halloween is a great idea and one that’s far too relatable. Plus. Dave as Austin Powers. The episode relegates Brad and Jane to spend Halloween in the suburbs and their solitary storyline over there does not disappoint either. Renegade trick-or-treaters and costumes gone awry is what Halloween is all about.


It’s Always Sunny in Philadelphia
“Who Got Sweet Dee Pregnant?”

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There was a bit of a bombshell when it was announced that Kaitlin Olson got pregnant and that her pregnancy would even be incorporated into Dee’s character on It’s Always Sunny in Philadelphia. While adding a baby to a series is fair cause for alarm (especially on a show like this), “Who Got Sweet Dee Pregnant?” happens to turn out to be one of the series’ weirdest, funniest episodes, and a lot of that good will comes from the fact that the gang mashes all of this up with Halloween. This episode juxtaposes the entertaining scares of the holiday with the very real scare that one of the gang is allegedly the father of Dee’s baby. Accordingly, everyone accounts their hazy, boozy Halloween night with the hopes of getting to the bottom of this awfulness. Plus, this episode also has some of the most broad, out there jokes in the entirety of It’s Always Sunny. There’s an unbelievable running joke in the episode where Dee is increasingly depicted as a giant bird during the stories, and it’s so damn weird and good. Also, Mac as Aragorn. So yeah.


Parks and Recreation
“Greg Pikitis”

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One of the first true classics from out of Parks and Recreation’s oeuvre. “Greg Pikitis” sees a determined Leslie using the brunt of her resources to take down the vandal that’s making working in the Parks Department so difficult lately. Parks and Rec is so good when the story is Leslie versus someone and “Greg Pikitis” is a great example of everyone getting collectively outsmarted and banding together to take someone down. The episode is incredibly solid when it comes to characterization and dialogue with Halloween being a particularly good look for the show. The only shame here is that Pikitis wasn’t made a yearly threat and a continual foe for Leslie to thwart, like Brooklyn Nine-Nine would do.


Cheers 
“Bar Wars V: The Final Judgment”

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And speaking of traditions, Cheers does some wonderful work with its many “Bar Wars” episodes, all of which are fantastic occurrences, but “Bar Wars V: The Final Judgment” is particularly wonderful. It works so well due to just how far it goes, its incorporation of an “actual” corpse, and that it also happens to be the favorite “Bar Wars” episode of Ken Levine, the co-writer of these yearly installments. This is the best sort of episode where you’re guessing the whole time if a prank is going on or not and when the other shoe is finally going to drop. “Bar Wars V” sets Sam against the rest of the Cheers crew as he is the lone person that believes that their rival, Gary, is not actually dead and really just pulling off the most elaborate “Bar Wars” prank of all time. It’s so, so good to see how unbelieving Sam is and if all of this is actually going to pull the rug out from under you or not. The episode juggles between outlandish prank and Sam simultaneously going through the stages of grief as he tries to process this loss he’s experienced. It’s surprisingly deep, with the ending also being just perfect, perfect comedy that I won’t dare spoil for you.


Community
“Horror Fiction in Seven Spooky Steps”

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Community is exactly the sort of wonderfully inventive show that treats Halloween with respect. This is a show that turns out a flawless claymation or musical installment for Christmas and then will do a Hearts of Darkness homage for absolutely no reason at all. Everyone goes on about Community’s Halloween zombie episode, but let me argue that “Horror Fiction in Seven Spooky Steps” is the stronger episode. “Horror Fiction” not only has a super self-aware script by series creator Dan Harmon himself that captures the spirit of telling scary stories around the campfire. Somehow Harmon crams seven complete, hilarious stories into this episode and it’s just a feat in storytelling.


Boys Meets World
“And Then There Was Shawn”

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So for some reason Boy Meets World decides to do a slasher/Agatha Christie parody and it’s maybe their greatest episode of all time. They even go as far as casting a ’90s Jennifer Love Hewitt in the final girl role. Rather brilliantly, the episode uses this stylistic swap as a means of commenting upon what’s going on with Shawn, his new relationship, and Cory. This “mental break” that’s being experienced makes total sense in the context, but it’s just so much fun to see tropes like power outages, lightning, and dramatic music stings all perfectly landing. This might not even be a Halloween episode per se, but it’s got a high body count and endless love for the slasher genre. It’s worth mentioning that Boy Meets World would also do an homage to Psycho in “The Psychotic Episode,” which is also a ton of fun, but this one just does it all better. Someone needs to get Girl Meets World to start doing spiritual sequels to these scary episodes, stat.


Brooklyn Nine-Nine
“Halloween Trilogy”

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If there is any modern contemporary to Cheers’ annual “Bar Wars” challenges, it’s Brooklyn Nine-Nine’s charming “Greatest Detective/Genius” recurring contest. These episodes have pitted Peralta against Holt (and increasingly more of the 99) in an extreme measuring of skills that uses the frivolity and erratic nature of Halloween to its advantage. The series just did their fourth installment of this and it doesn’t seem to be showing any signs of slowing down. With different flairs and aspects being present in each year’s competition, things also stay fresh without this feeling derivative each time. If anything it’s exciting.


Frasier
“Room Full of Heroes”

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Frasier is the sort of high brow show that can spend an entire episode on wine tasting, the opera, or charting the lineage of some Russian family tree, but it’s a show that’s also capable of delighting in such silly frivolity, with “Room Full of Heroes” very comfortably falling into the category of the latter. The episode in question sees Frasier throwing one of his trademark parties, with this one having the Halloween-related caveat that everyone most come adorned in the costume of their hero. This results in some fantastic costume decisions, including Roz as Wonder Woman, Frasier as Sigmund Freud (not Fidel Castro), Martin as Joe DiMaggio, Daphne as Elton John, and Niles, brilliantly dressing as Martin. It’s endless fun to just watch this crew play as their personae for an episode, but the real gem here is in the double dose of Martin that we get. Watching Niles perfectly imitate Martin, creating an echo effect in the room is fantastic, and the feud and jealousy that it starts between Frasier and Niles is trademark Frasier material. This Halloween installment has a lot of fun, but it’s also not afraid to pack some personal issues and get emotional for a minute.


South Park
“A Nightmare on Facetime”

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South Park has done a number of great Halloween episodes, and this technically isn’t one of them, but I felt like getting a little crazy here and this episode is an inspired Shining homage, so let’s give it a break. Randy comes into possession of a Blockbuster location on its last legs and impulsively moves his family in with the most optimistic of expectations. It’s so, so funny to see this dead chain sucking out Randy’s soul, making him go crazy while also faithfully riffing on the beats of the classic film. This idea sneaks up on you and don’t realize how solid a concept it is until it’s deep in the thick of it all. Besides, when is a Randy episode of South Park ever a bad thing?


Millennium
“The Curse of Frank Black”

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Millennium came onto the scene with great potential, acting as a second more extreme, religious-based series for Chris Carter while The X-Files was operating at peak popularity. While Carter’s dour series failed to catch on and underwent multiple facelifts, it’s agreed by many fans that the series’ Halloween episode, “The Curse of Frank Black” is one of the show’s very best entries. “The Curse of Frank Black” is watchable even if you’ve never seen an episode of the show before. It almost feels like a haunted, mostly silent short film that just happens to feature Frank Black in it. The episode largely sees a stoic Frank wandering the streets on Halloween and taking in his life and what’s become of it (not to mention how he’s viewed by others). It might not be the most exciting Millennium episode and it doesn’t throw a bunch of demons or serial killers at you, but it’s a tragic tone piece that highlights how strong of an actor Lance Henriksen is.


King of the Hill
“Hilloween”

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The marvelously dry King of the Hill with Hank disapproving (“The boy ain’t right”) and raining on his parade. So when that cross section of interests intersects with Halloween, things get particularly interesting. The episode manages to open a pretty engaging, thought provoking conversation on the Pagan aspects of the holiday and what’s the “right” behavior for this spooky holiday. Plus, what’s more inspiring than Hank and friends proudly marching through the streets chanting “Trick or treat!” as if it’s some protest chant?


Tales From the Darkside
“Halloween Candy”

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Tales From the Darkside might not feature as many classics as Tales From the Crypt, but that doesn’t mean that the anthology series is without its merits. “Halloween Candy” is a disturbing entry that’s directed by Tom Savini and widely considered to be one of Darkside’s best and scariest episodes (including the George A. Romero scripted pilot, “Trick or Treat”). The story looks at a terribly bitter old man, Michael Killup, who doesn’t want to give candy out to self-entitled children, with his grown son even trying to cover for him. Killup’s aversion to children is kind of insane. He just doesn’t want to give them candy. As thin as a character trait as that makes, it still works. Moments like where he’s dishing out “goblin candy” to kids highlights just how much of a callous asshole the man is. We’re literally given no reason to want to root for him. You want to see him get his just desserts. It’s all beautifully constructed.

After Killup has sufficiently broken the dreams of the neighborhood children, a troll inconspicuously joins the scene and Savini’s work with it is great, terrifying stuff. Savini chooses to show the troll through quick flashes and clever angles to make him even scarier. There’s a great sense of dread building through all of this as Killup gets victimized. The in essential doorbell becomes an increasingly terrifying sound. The phrase “Trick or treat” likewise becomes downright menacing by the end of the episode.  There is also plenty of horror here stemming beyond the troll, like in a set piece involving a crawling bag that ends up being full of bugs. It’s a fantastic visual. Later on when even Killup’s eggs explode with cockroaches, it’s even more effective. There’s also an added time loss aspect to things where it seems like this Halloween nightmare is never going to end and that this man is trapped in purgatory. And talk about creepy endings!

Lists by design have to leave things out, so tell us what the glaring omissions are here in your opinion. Maybe you’re a fan of How I Met Your Mother’s “Slutty Pumpkin” outing. Does NewsRadio’s Halloween installment need to be on here? Or do you consider ALF’s “Some Enchanted Evening” mandatory Halloween viewing? Sound off and trick or treat!


AROUND THE WEB


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