Sacred Walloween: Top Ten Best Halloween Specials

Welcome to Sacred Walloween! Today, we’re gonna be looking at the best Halloween Specials. TV shows love to celebrate holidays, and they release entire odes to it. Halloween is no different-costumes, pumpkins, scares, etc. cover our favorite shows. And while some fail miserably, some end up creating classic episodes in their universe’s lexicon.

I’m going to stop beating around the bush and cut straight to the Honorable Mentions. “Horror Fiction in Seven Spooky Steps” was a Twilight Zone-esque masterwork for Community. Frasier had two great episodes in “Halloween” and “Room Full of Heroes.” Monk got into the game with the bittersweet “Mr. Monk Goes Home Again.” “Night of the Day of the Dead” was a high point for not only Lizzie McGuire, but Disney Channel itself. Freaks and Geeks’s “Tricks and Treats” was a heartwarming sibling bonding homage complete with an appearance by Bionic Woman. And both Brooklyn Nine Nine and Roseanne have made annual traditions out of their Halloween specials, focused on pranks and fun-loving shenanigans. However, while these episodes are funny, scary, and heartwarming, often at the same time, the Top Ten are not only high points in their show, they often feature character growth imperative to the show. Oh, and one episode per show. Sorry, thems the rules So let’s take a look at the Top Ten Best Halloween Specials.

10. Fear Itself-Buffy the Vampire Slayer

In the grand scheme of things, “Fear Itself” isn’t one of the best episodes in Buffy’s classic run. It’s not the funniest episode (that would be “The Zeppo”), and it’s not the scariest (that would be “Hush”). But it does feature the true spirit of Halloween-some scares, pranks, and good clean fun. Each character confronts their biggest fears, some of which cover arcs of the entire series, all while confronting demons, witches and werewolves (which often means fighting themselves), in scenes alternating between horror and comedy. While it’s frightening to see severed heads and eyeballs, it’s also hilarious to see Giles with a chainsaw and a six-inch tall demon screaming bloody murder. Overall, “Fear Itself” drives to the heart of our heroes’ souls, and provides us the best of not just the show (horror-comedy), but the best of the holiday (horror, pranks and chainsaws) as well.

9. Graveyard Shift-Spongebob Squarepants

This is the biggest stretch on this list. The episode didn’t originally air during October or near Halloween. However, it has since become synonymous to the holiday. And I really wanted to have a kid’s classic for the list (“Frankenpooh” and “The Ghost of Suite 613” by The Suite Life of Zack and Cody came the closest). So I decided to make one exception to my usual rules. And how could I pick anything other than “Graveyard Shift?” Not only one of the best episodes of Spongebob Squarepants, but a childhood classic. After being forced to work all night by their boss, the depressed and cynical Squidward decides to scare his coworker, the naïve and innocent Spongebob, with a ghost story. It’s actually a somewhat frightening story, but still childish and fun. However, the joke’s on him when his myth may turn out to be real. The jokes are a mile a minute, on par with the best of the Looney Tunes, and actually gets to the heart of the characters in a way lots of other episodes don’t-Mr. Krabs’ penny-pinching ways, the cosmic failure of Squidward’s luck, and Spongebob’s happy, upbeat nature. And of course, there’s the immortal Nosferatu joke. If you are under 13 (or older, it’s still a classic), this is the pinnacle of Halloween episodes.

8. The Haunting of Taylor House-Home Improvement

One show that really enjoyed letting loose on Halloween was Home Improvement. Tim Allen’s 90s sitcom really captured something sweet and funny about families in a way that most sitcoms still struggle to do. And it is really on display in this episode. It’s got all the marks of a general Home Improvement episode-an episode of Tool Time where Tim cause Al (Richard Karn) harm, Brad (Zachary Ty Bryan) having relationship issues, Jill (Patricia Richardson) alternating between voice of reason and just as neurotic as her family, Wilson (Earl Hindman) being weird yet wise, and Randy (the immortal Jonathan Taylor Thomas) being sassy. However, it also had a sense of the Halloween spirit that really captured the show’s energy: Tim just wants to build the perfect haunted house while helping his family deal with their issues, Jill deals with her husband’s childish behavior, and everyone leaves happy. Well, everyone but the bad boy who steals Brad’s girl. Side note: Rider Strong should be in everything. Side side note: never dress as Raggedy Andy, kids. It’s just weird. Poor Brad.

7. Who Got Dee Pregnant?-It’s Always Sunny in Philadelphia

Rashomon is widely considered one of the greatest films of all time. It takes the idea of truth and shows its subjectivity to each person, making the audience question what is real and what is just a story. So naturally, the trashiest show on television is of the right caliber to take on a spoof of such a monumental film. However, from the desire to just make a trashy Halloween episode came one of the most brilliant Halloween specials of all time. Centered around the season’s arc (and real life event) of Dee’s (Kaitlin Olsen) pregnancy, the gang begins to panic over the revelation that one of them got her pregnant last Halloween. The gang had “browned out,” so they have to put together their own memories to figure out who was responsible. What results is not only a building world of absurdity, but also one of the best looks into the minds of the characters the show has ever given: Frank’s (Danny DeVito) memory is sex-filled and filthy, Dennis’ (Glenn Howerton) only recalls his own actions and his disturbing pursuits/assaults of women, Charlie’s (Charlie Day) is simplistic and happy, and Mac’s (Rob McElhenney) is delusional to the extreme. They are also each in costume for the night, to absurd degrees: Dennis is Luigi, Mac was supposed to be Mario but instead went as “Virgil Morgenstein (Viggo Mortensen as Aragorn), Charlie went as the Phantom of the Opera, Frank is Man-Spider (a horrifying half man-half spider creature), and Dee is an angel, which the Gang mistakes for a bird, resulting in a brilliant visual gag where Mac is shown to envision Dee as a literal ostrich). The episode twists, it turns, it’s disturbing, and it shows us the Gang’s true soul. It’s the modern Halloween classic.

6. Slutty Pumpkin-How I Met Your Mother

People often forget, mostly because of a weaker back half and a god-awful series finale, but at one point How I Met Your Mother was one of the best shows on television. The reminiscings of fatherly Ted (Josh Radnor as a youngster, Bob Saget as an adult) as he tells his kids the story of the eight-year quest to meet their mother as he hung out with his wild and crazy friends in the present day, the show told lovable, Friends-like stories through creative and brilliant twists. One such episode revolves around Ted’s quest to wait all night at a Halloween party for a girl in a pumpkin costume. If this sounds familiar, it’s because it’s a sendup to another special on this list. The show helps solidify the romantic nature that exists within Ted (with this being the sixth episode of the show, it may be the earliest sign), as well as establishing traits of other members in the group-Marshall and Lily’s (Jason Segal and Alyson Hannigan) relationship, Robin’s (Cobie Smulders) inability to form lasting relationships, and Barney’s (Neil Patrick Harris) crazed narcissism. It’s a sweet, funny and touching episode, and coming just six episodes into the run of the show, it helped solidify it as the classic people now regard it as.

5. Halloween-Modern Family

I’ve always found it weird how most classic shows are at their peak during the second season. One of the most recent examples of this is Modern Family, a show that still is funny eight years in, but will never be the truly groundbreaking experience it was in 2010-2011. One of the best episodes of that season was their Halloween episode. Most Halloween specials fall flat if the ensemble isn’t into it. However, if the ensemble is all in, and they have this level of chemistry, you’re onto something great. Here we have Julie Bowen’s crazed perfectionist, innocent Ty Burrell’s quest to avoid a divorce with his beloved wife, Eric Stonestreet being an emotional mess, uptight Jesse Tyler Ferguson embarrassing himself the one time he tries to cut loose, and Sofia Vergara’s all-around talent as both a form of slapstick and vocal farce. The episode works across the board, with funny jokes, touching family moments, and a laugh-out-loud moment involving a voice enhancer. I didn’t understand at the time why the show had one the Emmy its first time out. I understood it the day this episode aired.

4. Halloween Candy-Everybody Loves Raymond

One of the most underrated sitcoms in history is Ray Romano’s Everybody Loves Raymond. The level of absurdity that the little Italian family in New York goes through every episode is peak comedy writing, and the way the cast interacts makes them feel like a real family, instead of just actors. One of their more brilliant episodes is their Halloween special, simply because it is barely a Halloween episode. The bulk of the episode revolves around the sex life of married couple Ray and Debra (the phenomenal Patricia Heaton)-which goes to demonstrate the brilliance of the writing, because the word “sex” is never said the entire episode. It’s all metaphors and euphemisms. Basically, Ray has a desire to increase his sex life with his wife, and buys condoms; realizing that with the kids out of the house trick-or-treating, they have a chance to be intimate when things quiet down. This is where Halloween enters the picture-not as a convenience, but as a plot device. It’s brilliant. However, things go wrong when grandpa Frank (Peter Boyle, dressed as Frankenstein as an homage to his role in 1974’s Young Frankenstein) mistakes the condoms for chocolate coins-not only ruining Ray and Debra’s chances of getting lucky, but also embarrassing them in front of the entire neighborhood. It’s brilliant writing, and it stands out amongst the best for that very reason.

3. Halloween-The Office

If there’s one live action show that dominated the Halloween season, it’s The Office. Given the unfair advantage of taking place in an office building, and thus reflecting reality, the show allows us to see our favorite characters cut loose the way real people do on Halloween, dressing up as a black cat, wearing a fake papier-mâché head, dressing as Dorothy Gale, or being a Sith Lord. Of course, we all know that person who never took anything seriously and refused to embarrass himself, wearing a simple outfit, like 3 black stickers, to create “Three Hole Punch Jim.” It’s a sense of realism, amongst the characters and amongst the viewers, that makes these episodes such a relatable experience. However, the reason I’m going with the first episode, “Halloween,” from season 2, is because this episode is actually important. You see, when the show first aired, Michael Scott was supposed to be a direct correlation to David Brent: an unbearable, kinda racist, kinda sexist prick who you hate as a boss and as a person. And sure, these types of bosses are relatable. But it seemed old hat by the time Steve Carell started playing Scott. Which is why Carell chose to make a change. He shifted Scott’s personality-instead of being an unlikeable idiot bigot, he was now a well-meaning but bumbling guy. Instead of thinking everyone liked him out of narcissism, like Brent, Scott thinks everyone likes him because he likes everyone. It’s a change that made the show one of the best on TV, and changed the game completely. The first signs of this come in “Halloween.” Michael spends all day lamenting at the realization he’ll have to fire someone. He spends his Halloween bumbling through the decision, changing his mind multiple times, asking everyone’s opinion, and suffering at the hands of the economic downturn. When he’s finally convinced to fire a background character (and, ironically, supposedly the only person there who is decent at their job), he asks him if “they can still be friends.” In response, the former employee smashes a pumpkin on Michael’s car. The true joy of the episode, however, comes as Scott heads home, dejected and beaten from his day at work. However, the smile on his face as he opens the door to give candy on his kids is no fake-the promise of innocence and escapism helps him fight off the hurt, and give a sense of empathy and catharsis to a character who previously didn’t deserve it. What I’m saying is, if “Halloween” hadn’t been so good, The Office would never have been a hit.

2. Treehouse of Horror IV-The Simpsons

But if The Office owns live action television’s take on Halloween, The Simpsons thoroughly dominate it. Treehouse of Horror is pretty much a holiday staple, like Rudolph at Christmas. I could have filled this entire list with Treehouse of Horrors if I wanted to, but I made a rule that each show only gets one special, so I had to narrow it down. Most fans prefer V, thanks to “The Shinning.” And the first was so good I almost picked it. However, if you’re asking me which is the only episode to feature three absolutely great sketches without any misses, it’s IV. The episode starts by taking on the classic “The Devil and Daniel Webster.” And if you ask me, this is one of their best vignettes ever. The idea of Ned Flanders as the Devil is inspired. The Forbidden donut is brilliant. And Homer in Hell is one of the funniest moments in Simpson history. Of course, there’s also the trial, which features the Jury of the Damned (including a Not-Dead-Yet Richard Nixon), and an appearance by failed lawyer Lionel Hutz, played by the incomparable Phil Hartman. Then we get the Twilight Zone, and a funny send-up at that, thanks to Bart, Otto, and once again, Ned Flanders. Finally, we get “Bart Simpson’s Dracula,” a sendup to the incredibly cheesy Francis Ford Coppola film. The idea to cast Mr. Burns as Dracula is ingenious, but not as brilliant as the Head Vampire being Maggie. That baby is the best. The episode ends with the family gathered around and singing “Hark the Herald Angels Sing.” This is fitting, because #1 is so obviously…

1. It’s the Great Pumpkin, Charlie Brown!

Is this really that surprising of a pick? It’s the most famous Halloween special of all time. It’s the only one that is shown annually, and has been for 50 years. It’s the only one that truly speaks to childhood. Sure, it’s not an episode of a TV show, like the rest of these. But it’s so much more than that. It features the greatest hits of fall, Halloween, and childhood-football, jumping into leaves, carving pumpkins (“You didn’t tell me you were gonna kill it!”), trick or treating (and getting only rocks), bobbing for apples, and spending time with siblings, no matter how idealistic/stupid they are. From Snoopy fighting the Red Baron to Schroeder’s World War I medley to “I’ve been kissed by a dog” to Linus’ optimistic desires to see the Great Pumpkin, the clip is filled with pop culture staples, and stands out as the greatest Halloween special of all time.

What about you? Do you have a favorite Halloween special? Any I’m forgetting? Let me know in the comments. In the meantime, I’m going to go check my local listings to see what night Charlie Brown will grace my presence. Stay spooky, and remember to be surprised when they do the Mash!