Staff Picks: Favorite Halloween Episodes/Specials

With it being Halloween, we at The Pop Break decided to get together and highlight our favorite episodes, TV movies, and specials from the Halloween season. We were going for a less obvious list, so don’t be alarmed that It’s the Great Pumpkin, Charlie Brown is not here. We love it as much as you do.

With that in mind, here are Our Favorite Halloween Episodes/Specials.

Pokémon, “The Ghost of Maiden’s Peak”

Okay, this choice may technically not be a Halloween episode, but I think that any TV episode that features ghosts and comes out in October is a de facto Halloween episode. Few people (unless their nostalgia goggles are glued on) will defend Pokémon as being a truly great television show, yet there are a handful of episodes that I can sincerely consider entertaining. “The Ghost of Maiden’s Peak” is one such episode in large part because the episode breaks from the show’s typical formula and finds a strong balance between spooky and comedic. Turning Brock’s obsession with beautiful women into a dangerous vulnerability is a clever excuse for introducing the seductive ghost that haunts the city, and the ghost itself generates an entertaining air of mystery and peril.

What most sets this episode apart in my mind, though, is the ending. My favorite part of most spooky/ghost stories is the twist at the end, the last-minute reveal that the monster is actually real, still alive, or not who you thought it was. “The Ghost of Maiden’s Peak” concludes on such a note and instantly adds a greater sense of tragedy and eeriness. The result is an incredibly memorable episode that is equal parts sidesplitting, heartbreaking, spine tingling.

–Josh Sarnecky

Buffy the Vampire Slayer, “Fear, Itself”

Out of seven seasons of Buffy and multiple Halloween related episodes, “Fear, Itself” is my go-to episode year after year.

Buffy is a freshman at Sunnydale University, attending her first college Halloween party at a fraternity on campus. After a previous Halloween where everyone turned into their costumes, Buffy comes dressed as Little Red Riding Hood with a basket full of weapons, just in case. Once at the party, however, Buffy and friends quickly discover that things aren’t quite right and people’s fears are coming to life. They later discover that a symbol has been painted on the floor, which brings forth a fear demon who takes away all exits to the house and the only way out is to destroy the demon.

I love the episode because there are so many great one liners and memorable moments. My favorite moment is when Xander tells Anya to come dressed as something scary and she shows up dressed as a bunny, the scariest thing she could think of. The ending is the absolute funniest part, but I won’t give that away.

If you want to understand the references to the costumes they choose, you can start with the episode “Halloween” from Season 2, but “Fear, Itself” is fine holiday fun on its own.

–Ann Hale

Over the Garden Wall

Granted, this show isn’t exactly a Halloween special. Over the Garden Wall is a miniseries that first aired on Cartoon Network on November 3, 2014, so a few days after Halloween. It’s a series that is more celebratory of fall in general than it is of any one specific holiday, but the creators drew visual inspiration from vintage Halloween postcards, Victorian chromolithography, and the landscapes of New England, to create something hauntingly beautiful and distinctly spooky. Every year since its debut, I have made a point to wait for the perfect chilly night in October to enjoy some apple cider and watch it, in what has easily become one of my favorite holiday traditions.

In Over the Garden Wall, two brothers find themselves lost in the woods and attempt to get home, leading them to get lost further into “the unknown” and wander in and out of stories that seem to come straight out of a fairytale. There’s a town of strange pumpkin people who aren’t keen on visitors. A lonely millionaire who is unsure if his mansion is truly haunted by ghosts, or if his solitude has driven him to madness. A young woman possessed by an evil spirit that compels her to consume unsuspecting travelers. There are witches, skeletons, ghosts, demons, monsters, talking animals. Pretty much everything you look for in a good Halloween special. Some of these episodes are genuinely unsettling even for an adult, but wrapped up in a fun, compelling story that is endlessly enjoyable for children. It also happens to have some of the most breathtaking artwork you’re likely to see in a cartoon. Watch it on Halloween and be sorry you didn’t think to dress up as one of these characters sooner.

–Melissa Jouben

Don’t Look Under the Bed

When I was growing up in the ’90s, the best Halloween specials came on Disney Channel. One of my favorites will always be Don’t Look Under the Bed. This movie was actually decently scary, at least if you were a kid. It actually spiked some controversy because parents claimed it was too dark for the children and the movie was taken out of the regular rotation, which is a bummer because its seriously a solid movie but I also totally understand.

Don’t Look Under the Bed debuted in 1999. It tells the story of Frances McCausland, who is very intelligent and about to start high school a year early. But weird things start happening around town, mostly little things like alarms going off crazy early or eggs covering teachers’ vehicles, the most unique thing though is the letter B being spray painted all over town. As the occurrences increase and get a bit less playful, signs start pointing to Frances as the culprit (like her locker being the only one without a B, or her house being the only one whose Christmas lights turn on). Frances is running out of logical answers and her world is drastically changed when she meets Larry Houdini, an imaginary friend who tells her that these happenings are all the work of the Boogeyman.

This may seem rather whimsical, and at it’s core, it is. However, this movie gets really dark, really fast. The Boogeyman is actually pretty scary looking (at least to a child) and after Darwin stops believing in Larry due to Frances telling him to “grow up”, we watch as Larry slowly starts turning into a monster, try as he might to fight it. Darwin gets pulled under the bed and taken to Boogey World, and Frances alongside the Larry (who is slowly going insane) must enter to find and save him. It’s literally a child’s nightmare. The Boogeyman living under your bed and waiting to take you. Even so, the movie still retains its comedic moments and there’s an epic fight between Larry and the Boogeyman with a twist at the end of the true identity of who the Boogeyman is. I really can’t think of another movie that’s anything like it and that makes it even more unique.

–Rachel Freeman

Scooby-Doo on Zombie Island

Scooby-Doo on Zombie Island technically landed on home video first, but Cartoon Network aired the movie on Halloween the following month. No matter who you are, chances are you’re familiar with at least one of Scooby-Doo’s various incarnations. The franchise has a tried-and-true formula that’s worked for decades, though this does make most of the stories essentially the same. This flick is different.

Shows like The 13 Ghosts of Scooby-Doo featured actual monsters, but Zombie Island makes a conscious effort to challenge the established tropes. Nothing depicts this better than Fred’s attempt to explain the zombies as phony, only to pull the head off of one and figure out it’s all too real. I’ll admit that I was as terrified as the characters when I was a little kid. In fact, Zombie Island scared me so much that I avoided rewatching it for years.

I now look back Scooby-Doo on Zombie Island fondly as the cleverly written, wonderfully animated movie that it is. The sequel, Scooby-Doo and the Witch’s Ghost is pretty good too, even if it’s largely a retread. Still, it’s Zombie Island that deserves bulk of the praise. It’s worth checking out if you haven’t seen it.

–Aaron Sarnecky

Toy Story of Terror

While this may not be the most obscure, or deep cut choice for this list — it’s still one of my favorite television specials to watch on Halloween.

Toy Story of Terror is a delightful 30-minute special (21-minute actually) that finds all your Toy Story pals stuck in a motel run by an unscrupulous hotel manager (voiced by Stephen Tobolowsky AKA Ned Ryerson from Groundhog Day). The manager, like most villains in this series, wants the toys for his own personal collection so he can sell them off to the highest bidder. The story is framed like an old timey horror story, thanks to the continuous narration of one of my all-time favorite animated characters, Mr. Pricklepants (Timothy Dalton). We’ve also got the fantastic addition of Combat Carl voiced by Carl Weathers, who is in all his hyper-masculine glory here.

Nothing in this special is scary, but it’s truly charming, and a joy to watch. All the voices from the Toy Story movies are back, and it’s just great to see all these characters doing their thing onscreen. If you have kids, this is must-watch.

–Bill Bodkin

Check out The Pop Break’s review from 2013 here.

Founded in September 2009, The Pop Break is a digital pop culture magazine that covers film, music, television, video games, books and comics books and professional wrestling.

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