Unlike the rest of the “very special episodes” of our favorite sitcoms, nobody’s about to wind up pregnant or addicted to caffeine pills this week. Because it’s Halloween – and that means even the fuzziest of shows are about to get a whole lot creepier.
For some reason, even shows that are entirely grounded in reality will make up some ridiculous, unexplained supernatural plot at least once in its run, and for that we are endlessly grateful. There’s nothing quite as memorable as watching beloved characters get mysteriously killed off “I Know What You Did Last Summer” style, or thrown into the most horrifying of situations. Especially if they’re fifth graders and they’re boarding a ghost train to hell.
Read on to explore our ENT staff’s list of the greatest Halloween episodes of all time. But you better turn your night light on first.
“Slutty Pumpkin,” “How I Met Your Mother” | Holly Coletta
Call me a hopeless romantic, but there’s something seriously endearing about a guy who’s convinced that his one true love (and future mother of his children, obvs) dresses up like a slutty pumpkin for Halloween.
The premise is super “How I Met Your Mother”-y: Ted spends every Halloween at a party on their apartment building’s roof because one night four years ago he met The Perfect Woman in a pumpkin outfit (with strategically carved bits) who spent time studying penguins and told him about her specialty drink (“Tootsie Roll,” which is Kahula and root beer. I haven’t actually tried it, but you know it’s on my “HallOUween 2012” bucket list) and then wrote her number on a Kit-Kat wrapper. Ted loses the wrapper (because of course), but thinks his Jack-o-Lady will recognize him if he keeps showing up to the party dressed as a hanging chad.
The sidestory involves Lily, Marshall and Robin having real talk at McLaren’s because the Canadian is being annoying and refusing to like Halloween or couple-y things. Lilly and Marshall are also gag-inducingly couple-y cute as a pirate and his parrot (His actual parrot, guys. Get your mind out of the gutter), and Barney is Barney-y and wears like five outfits and hits on five different girls and gives himself high fives like five different times.
“The Slutty Pumpkin” might not be the best HIMYM episode ever, but it harkens back to the sitcom’s best era, a.k.a. before the time-suck of Ted-and-Robin, before the awkward dramedy of death and pregnancy problems, before the lackluster sequel called “The Slutty Pumpkin Returns,” before Barney’s catchphrases became less funny than internet memes and before Ted Moseby’s quest for happy monogamy felt tedious and tired.
Plus, this episode is bookmarked for me as the Exact Moment I Fell in Love with Jason Segel (it’s when he compares penguins to “black-and-white Ewoks”).
Love or hate the series as a whole, but you can’t deny that the Slutty Pumpkin episode is legen…wait for it…dary.
“Treehouse of Horror IV,” “The Simpsons” | Ross Dickerhoof
Yes, yes, I know. Almost all of the Treehouse of Horror episodes are fantastic (I’m particularly fond of the satirical take on “The Raven” from I and “The Shinning” from V), but this is the one that’s the strongest all around.
As is often the case, the first segment, “The Devil and Homer Simpson,” is the best. After selling his soul to the Devil (who happens to be Flanders, because “it’s always the one you least expect”) for a doughnut, Homer is sent to Hell and must await a trial to determine whether or not he is worthy of eternal damnation. There’s lots of great gags here (Homer being force-fed doughnuts endlessly as an ironic punishment… only to keep demanding more), and they come hard and fast, leading up to a hilarious ending.
The second segment, “Terror at 5 ½ Feet,” isn’t quite as good and is a lot more simplistic, but has its charms. This bit parodies the classic “Twilight Zone” episode “Nightmare at 20,000 Feet,” changing the setting to a bus and placing Bart in the William Shatner role. Bart sees a gremlin loosening the lug nuts on the wheels, but no one else seems to, causing him to try and stop the beast before it kills everyone. It’s rather predictable, but fans of the parody’s material will surely be impressed, and there’s several good laughs to be found (particularly a bit involving Flanders and the gremlin).
The final segment, “Bart Simpson’s Dracula,” is a spoof of “Bram Stoker’s Dracula” and “The Lost Boys,” and it provides a nice cap to the episode. When the family is invited to Mr. Burns’ castle in Pennsylvania, Lisa and Bart discover that he is actually a vampire. Burns turns Bart into a vampire as well, and typical Simpsons chaos ensues. It strikes the right balance between creepy and funny, and the ending is so unexpected and gut-busting that you’ll wish every “Treehouse of Horror” episode had an ending this good.
“Night of the Day of the Dead,” “Lizzie McGuire” | Carina Belles
Not only can “Lizzie McGuire” boast the greatest TV parents of all time (sup, Robert Carradine), it also blessed us with the scariest Halloween episode to ever grace the Disney Channel. Don’t believe me? Yeah, that’s what I thought.
In one of the best examples of the fine line between stereotyping and cross-cultural education, Miranda wants to bring her family’s Dia de los Muertos heirlooms (aka a terrifying pair of skeletal bride and groom mannequins) to the school Halloween party. Kate, flawless queen of the universe, is not amused. Not only does she hate Miranda’s cheap taste in decor, she won’t let Lizzie rule over the haunted janitor’s closet in a sexy vampire costume! Instead, she must hand out balloon animals to sticky children in an even stickier clown costume. Vengeance is imminent. (For the record, Kate is a hotter vampire).
With the help of Lizzie’s beyond irritating kid brother, my future husband Gordo and Miranda’s parents (who are way cool because they love torturing middle school mean girls) Kate finds herself on the hit list of a pair of ghoulish ancestors. Word to the wise: Don’t mess with Miranda, or her dead relatives will trap your soul in a bobblehead and send a possessed Hilary Duff to come kill you.
“Haunted Train,” “Hey Arnold” | Conor Morris
You know what’s awesome? “Hey Arnold!” You know what else is awesome? Trains!
Combine those two with that most magical time of the year (Halloween, duh) and you’ve got one of the best Halloween specials ever: “Haunted Train.” Basically, Arnold and co. go to explore “Engine 25,” a train that was driven off of its tracks by an insane engineer and straight into, uh, “the fiery underworld.” The kids board a similar engine at the old abandoned trainyard near town, but after some scares and misunderstandings it turns out it’s not actually haunted – just a work train with this guy on board.
As Arnold is heading home after his night of scares, he gets all grumpy with his grandpa about making up stories. Soon after this scene, however, we see Brainy derping around on a fence as the real Engine 25 zooms by, driven by a crazy-ass accordion-playing stitched-up ghost dude who ain’t care about the rules of the road.
“Haunted Train” exemplifies what was so awesome about the “Hey Arnold!” seasonal episodes – it’s still the same goofy show, but it legitimately gets at the spirit of the holiday, especially with that final scene. I actually had nightmares as a kid after seeing that episode. It was spooky, okay!?
Also, Gerald plays the harmonica in it and sings a bluesy song about the ghost train, which makes any episode cool as crap in my book.
“And Then There Was Shawn,” “Boy Meets World” | Christian Law
Anybody who grew up during the nineties is already aware of the fact that “Boy Meets World” is one of the greatest shows of our generation. Who didn’t love the Matthews family and Cory’s group of friends? Heck, I met my first girlfriend by stalking someone from my class all the way to Disney World. Apparently, restraining orders are a lot easier to get than studio applause.
But there was always one episode that didn’t sit right with me. “And Then There Was Shawn” chronicled the death of pretty much every loved character on the series, and it absolutely terrified me. When the episode premiered, it was 1998. I was six freaking years old. Try explaining to a six year old that what happens on TV isn’t real. I thought Leonardo DiCaprio died on the Titanic until I was fifteen.
After the gang is given detention for disrupting class, everybody is stalked and murdered (kinda viciously for public TV) for a half hour. Whether it was death at the hands of a pencil or a well-placed pair of scissors in the back, watching your favorite characters get murdered as a child is traumatizing. Even if the whole episode was a metaphor for Shawn’s guilt at breaking up Cory and Topanga (still the coolest name in the history of ever), I never stopped being terrified of after school detention, because my teachers were never as cool as Mr. Feeny and they were much more prone to murder.
What’s your favorite special Halloween episode? Let us know in the comments or tweet us @SpeakeasyENT!