These 10 Halloween Specials will make your skin crawl (or remind you of simpler times)

These 10 Halloween Specials will make your skin crawl (or remind you of simpler times)
Photo by Szabó János / Unsplash

Who doesn’t love the spookiest time of the year?

One of the greatest highlights of syndicated television has got to be a series’ Halloween episode. And the beauty of the artform that is the Halloween episode is that it gives a television show license to add some scary elements that likely wouldn’t make it anywhere else in the show.

Oh, yeah, and expect a few spooky spoilers. Read at your own risk…if you dare.

It’s the Great Pumpkin, Charlie Brown

Okay, technically this isn’t really an episode, but rather a TV special.

Originally released in 1966, It’s the Great Pumpkin, Charlie Brown was a special based on Charles M. Schultz’s classic Peanuts comic strip, and features our glum protagonist navigating the Halloween season.

Charlie’s best friend Linus writes a letter to the Great Pumpkin, a sort of Santa Claus-like figure in the pre-Jack Skellington days. And though Linus and his not-so-secret admirer Sally are the only ones who believe in the Great Pumpkin, he sends his letter anyway.

Meanwhile, Charlie gets invited to a Halloween party by Violet. Before he shows up, Charlie and some of his friends go trick-or-treating. Charlie, of course, wears his iconic hole-ridden ghost costume and receives rocks, where his friends get candy instead.

And as this group of children go to their party, they find Linus and Sally sitting in the pumpkin patch to wait for the Great Pumpkin. The two wait all night, only to see Snoopy’s shadow instead of any sign of the Halloween figure. Though Sally is disappointed, Linus is not deterred and plans on doing the same thing next year.

As with most Peanuts holiday specials, they offer a sweet slice of nostalgia, even for those who weren’t alive when they first came out.

Boy Meets World - “And Then There Was Shawn”

This may be a controversial pick, as it technically wasn’t intended as a Halloween episode. We’re including it in this list, however, because despite airing in February, this ‘90s slasher parody would have worked so well as one.

After our main cast lands in detention, they find the words “No One Gets Out Alive” written on Mr. Feeny’s chalkboard. This is the first of many spooky scares that appear in the episode. Some have comical explanations, such as the sound of a loudly beating heart actually being a bouncing basketball. Though there are also plenty of genuinely horrific things that happen in this ABC sitcom episode.

A one-off character gets stabbed in the head by a pencil, Feeny is killed with a pair of scissors, and the normal janitor is killed and replaced by a much creepier one.

As the episode goes on, it plays on more and more slasher tropes, with Jennifer Love Hewitt even guest-starring in the episode. The best part of her showing up isn’t even just that she was in I Know What You Did Last Summer, but that that particular movie was about the manifestation of guilt. And at the episode’s climax, it’s revealed that Shawn himself is the “killer,” until he wakes up and realizes that he was only dreaming during detention. His dream was his own manifestation of guilt.

The episode is terrifying and, honestly, should have aired in October if you ask us.

The Suite Life of Zack & Cody - “The Ghost of Suite 613”

While this may have been a show made for children, don’t count this spooky Halloween episode out too soon.

The Suite Life of Zack & Cody was a Disney Channel sitcom that aired in the mid-2000s, about two mischievous twins living in a fancy hotel. In this season one episode, the boys are told about a haunted suite by the hotel’s heiress, London.

The rumor is confirmed by a maid, who tells the story of a woman who died after waiting three years for her husband to return from World War II. When she finds out that her husband cheated on her, the woman accidentally dies when she throws a gift from her husband into the mirror and shatters it.

The boys, London, and some of their friends on the hotel staff decide to investigate the haunted suite, which culminates in a challenge to spend the night in the room, and even perform a seance to contact the ghostly Irene. She seems to spirit everyone away until Zack is truly terrified.

Though the whole thing is revealed to be a prank to give Zack a taste of his own medicine, the episode ends with Zack and Cody returning to the suite to recover Cody’s lost security blanket, where they encounter the actual ghost of Irene.

If you have young kids and you want to watch a great Halloween episode with them, this is a solid choice.

Charmed - “All Halliwell’s Eve”

In a show about witches, one would have to imagine the Halloween episode is pretty  good, right?

The Charmed Ones, AKA the Halliwell sisters, Prue, Piper and Phoebe, are just trying to celebrate a normal Halloween when they are attacked by a pair of demons they vanquished two seasons ago. While trying to fight these Grimlocks off, the sisters are sent back in time through a portal, where they find themselves in the late 1600s.

As it turns out, the sisters were summoned by a good witch to help save a woman named Charlotte. See, Charlotte is pregnant, but has been kidnapped by an evil witch who intends on raising her baby on the dark side.

The sisters have lost their magical powers and have to adapt to the witchcraft available to them in their current time, while also avoiding witch hunters who try to execute them. The sisters are successful in their efforts to free Charlotte and help deliver her baby.

The baby turns out to be their magical ancestor Melinda Warren, whom they first met in another time travel-themed episode in the first season.

But the best part of this episode is that despite Phoebe’s griping about the classic cackling-witch-flying-across-the-moon-on-a-broomstick motif, she actually does this while back in time and creates the trope herself.

It’s a lovely Halloween episode with a rare historical twist that anyone can enjoy, but fans will appreciate even better.

Modern Family - “Halloween”

Sitcoms just do Halloween episodes the best, don’t they?

Modern Family is centered on the wacky misadventures of the lovable Pritchett-Dunphy family. And in their first Halloween episode, there are plenty of them.

From Mitchell mistakenly believing that everyone in his new office will dress up for Halloween and spending the rest of the day trying to hide his Spider-Man costume, to Phil and Claire trying to get their oldest daughter not to wear something too…inappropriate, this episode is full of classic Modern Family mishaps, but with a fun Halloween edge to it.

While Claire and Phil are trying to get their house ready for their annual party, Gloria and Jay get in a tiff because Jay teases his Colombian wife over her thick accent. But the funniest parts of the episode have to do with Cameron reliving his Halloween trauma from years passed.

As with a lot of Modern Family episodes, the episode gets wrapped up with some heartwarming moments, but that doesn’t take away from the humor or the frankly impressive Halloween party set-up the Dunphys came up with.

Brooklyn 99 - “Halloween”

Ah, the first Halloween episode from Brooklyn 99. The first of many Halloween Heists to appear throughout the series.

While Detectives Santiago and Boyle are out undercover, Jake Peralta makes a claim that he would be a great criminal. The seemingly no-nonsense Captain Holt is not convinced, so Peralta decides to issue him a challenge. If he can steal Holt’s Medal of Valor before midnight, then Holt will have to do Peralta’s paperwork and declare him to be an amazing detective. But if Holt wins, then Jake must work the next five weekends with no overtime, as well as keep a secret for the captain.

It’s a fun concept for a sitcom, and one that’s different from most, “We’re having a Halloween party” episodes, such as the previous entry on this list.

Peralta makes several attempts to snag Holt’s medal, even going so far as dressing up as a janitor to get access to the office. Naturally, Peralta is thwarted by the seasoned captain at every turn.

Or is he?

Peralta reveals to Holt that he has enlisted the other detectives to help him steal the Medal and that all of Jake’s attempts have just been diversions and that Detective Boyle has successfully stolen Holt’s Medal of Valor.

There’s a great reason why the writers of Brooklyn 99 kept coming up with more Halloween Heists, and that’s because episodes like this are just so much fun to watch.

The Office - “Halloween”

There are quite a few sitcoms known for their great Halloween episodes and the American version of The Office is one of them.

As the first season was a mid-season replacement, the original Halloween episode was featured back in season two. In it, the employees of Dunder Mifflin all dress up in costumes as they carry on through their workday.

At the beginning of the month, manager Michael Scott was tasked with firing one of his employees by the end of October, so of course he waits until Halloween to do something about it. Meanwhile Pam and Jim have posted their oddball co-worker Dwight’s résumé online to see what happens.

Dwight has a phone interview gone wrong and Michael tries to fire Creed. In an act of desperation, Creed convinces Michael to fire Devon, who does not take it well. The ex-employee smashes a pumpkin on Michael’s car and invites most of the staff to meet him for a drink. There’s a sweet moment where Pam apologizes to Jim for telling him he should apply for one of the jobs they found while pranking Dwight, and she tells him she would hate it if he left.

Though the plot rings as an average episode of the workplace mockumentary, it’s highlighted by the inclusion of ridiculous Halloween costumes, such as Michael’s extra head dummy and Dwight’s Sith Lord cape.

And though Michael is known for being an incompetent idiot, he is redeemed by the end of the episode when he takes delight in having trick-or-treaters come to his door. It’s a sweet way to close out the episode and give it more of a Halloween vibe.

Bob’s Burgers - “The Hauntening”

Bob’s Burgers is a wonderful somewhat family friendly animated sitcom. And one of the things it does best is the Halloween episode. Throughout its many seasons, there have been many spooky episodes, each featuring clever punny Halloween costumes from the Belcher children as they get into some sort of trouble while trick-or-treating.

In season six, however, things change.

Bob and Linda Belcher take their three children to a haunted house they’ve set up in a different neighborhood. Their youngest daughter, Louise, finds these sorts of things boring, and is not amused when her parents start a pretty lackluster performance.

As the Belchers prepare to leave, Bob discovers he has a flat tire and has no cell reception.

Things start to get very creepy as they return to the house. Metal grinds, the power goes out, and someone starts moaning terribly. The family travels through the house, trying to avoid the mysterious figure that’s chasing them, and even Louise loses her cool veneer. As the family resorts to climbing up onto the roof, they find a group of people in cloaks who seem to be performing some sort of ritual. And when things get dire, Louise admits that she’s truly terrified.

But instead of falling victim to this ritual, it’s revealed that the whole thing was the “real” haunted house, and that the family, as well as some of their friends, were behind it.

There are so many great Bob’s Burgers Halloween episodes, but this one sticks out because on first watch we end up just as scared as Louise, and on future viewings we can appreciate the twist even more.

Buffy the Vampire Slayer - “Halloween”

Another Halloween episode from a supernatural TV show.

Much like the Halliwell sisters from Charmed, Buffy Summers has dealt with many different demons and monsters in her time. But as she tries to be a normal teenager and enjoy this Halloween, things go a bit wonky.

The Slayer and her best friends stop by Ethan’s Costume Shop, where Xander buys an accessory for his army costume, Willow decides to be a ghost, and Buffy buys an 18th century-style dress to impress Angel, her vampire love interest.

When Halloween rolls around, Buffy and her friends go out to chaperone trick-or-treating kids. But while they’re out, everyone who bought a costume at Ethan’s shop has started to turn into whatever they’re dressed as, and most of them lose their memories, including Buffy.

Still with it, Willow finds Giles, Buffy’s Watcher, and together they seek out Ethan, who turns out to be someone from Giles’ past. Meanwhile, Buffy is cornered by Spike, who at this point is still a villain, and just before he takes advantage of her not knowing she’s the Slayer, Giles learns how to stop the curse.

It’s a really fun episode, and the perfect concept for a Buffy the Vampire Slayer Halloween episode.

The Simpsons - “Treehouse of Horror V”

Back in season two, the seminal animated sitcom The Simpsons started making their Halloween episodes an anthology. Each of these are called “Treehouse of Horror,” as the first one featured Lisa and Bart telling each other scary stories in Bart’s treehouse as Homer listened in.

Though we could pick any of these episodes to highlight in this list, we’ve chosen the fifth, which is arguably the most popular.

“Treehouse of Horror V” starts with a parody of The Shining, called “The Shinning,” where Homer works as a caretaker at his boss’s haunted lodge and takes his family along with him. While there, Bart develops “the shinning” and Homer goes crazy over time.

The second segment is called “Time and Punishment,” where Homer accidentally creates a time machine and learns a little something about the butterfly effect. He creates various timelines, but he cannot fix them or go back to normal. This was inspired by a short story by Ray Bradbury, called “A Sound of Thunder.”

The third part is called “Nightmare Cafeteria,” which was based on Soylent Green. In this segment, Principal Skinner starts having kids in detention butchered and served for lunch. Though a scant few children escape being eaten at school, they come home and become enveloped by a fog that turns people inside out.

These three parodies were incredible fodder for a Halloween show, especially with the running gag of Groundskeeper Willie getting hit with an ax in every story. It’s a great episode, and one that stands out in a long line of “Treehouse of Horror” episodes.

Halloween is such a fun time of year, so it makes sense for TV shows to celebrate and share those lovely spooky moments with us. Honestly, it seems the only negative to a Halloween episode is that sometimes the writers aren’t too creative with their names…

Well, that’s our list of the 10 BEST Halloween episodes! What’s your favorite? Which ones did we miss?