Ah, the Halloween episode. Using Halloween or similar scary elements as a narrative hook to see how characters we've come to love will react to the night of fright is a staple. Halloween Episodes are usually memorable for their scary moments, weird plots, and autumn aesthetics. There are probably hundreds of Halloween specials out there that I haven't seen or don't remember, but tonight I have a handful that I've re-watched lately and would like to share and give a couple of quick thoughts on.
"Boo Haw Haw" is a cartoon special that showcases the strengths of both the show Ed, Edd n Eddy and Halloween episodes. In it, Eddy leads the boys on a treasure map-hunt to find Spook-E-ville, a promised land of generous candy helpings. Eddy and Edd are doing their usual routines, but Ed is in peak Ed-form. Ed's been binge-watching Halloween movies to the point he's beginning to hallucinate that the other kids around the cul-de-sac are monsters and that he, Lothar, Viking ruler of Montezuma, has to defeat them to help the gang get to Spook-E-Ville. The expressiveness of Ed, Edd n Eddy's animation, always moving through wavering outlines even when nothing is actually going on, catches Ed's explosive fervor and absurd slapstick violence in hilarious moments of him mercilessly beating up everyone while shouting nonsensical quips and B-movie monster knowledge. The best Halloween episodes are never really about Halloween; they just use the night as writing fuel and character potential. "Boo Haw Haw" delivers though giving us an absurd episode amongst a sea of absurd episodes that still makes me laugh on re-watch.
King of the Hill's "Hilloween" shows a rarely seen side of main character Hank Hill. At his worst, Hank can be an overly-moralizing stick in the mud, but in this episode, Hank is rebellious one for a change when his Halloween traditions are called into question and censured by an evangelical church lady who deems Halloween a satanic holiday. Hank expectedly stands his ground stubbornly and takes a strong stance on keeping Halloween the way it used to be when he was a kid, which is shown through hilarious flashback. It's odd to see Hank in Bobby's or the culture war stand-in's seat for a change as the rogue element shaking the stability of Arlen, while another character becomes the stern, Hank-like conservative figure, buts its delivered in such an in-character way that it still works and speaks to a more well-rounded depiction of Hank in King of the Hill as not so much a social conservative but rather an individual of decades old sensibilities who has to navigate a changing world around him, often awkwardly. Hank learns new lessons all of the time, but in "Hilloween," it's one Junie Harper that has to learn a lesson. The episode just goes to show how conflicted society was in the 90s if Hank Hill looks rebellious, and his righteous indignation is supported by the people of Arlen and we the viewers.
Gravity Falls is a show all about the spooky happenings of the Pines family and friends as they encounter monsters, magical creatures, strange artifacts, and other weird things that sometimes push the bill for a Disney property. Since the show is set during one summer, its Halloween is instead a summer-based spoof complete with its own lore like Jack O' Melons instead of Jack O' lanterns and a monster named the Summerween Trickster. The Trickster is among the show's most memorable one-off antagonists for his frightening appearance and creepy presentation as a nimble, long-legged monster that can scour buildings like a spider and reform from being destroyed. He borrows elements from other monsters like Spirited Away's Noface, Trick 'r Treat's Sam, Internet Legend's Slenderman, and Batman Villains Scarecrow and Clayface to make a monster that feels like an embodiment of Halloween and its cobbled together elements that frequently borrow from and compound with one another. Aside from having a cool monster, the episode delivers the series' usual quirky humor and heart about the struggles of growing up and being a family while celebrating Halloween tropes.
The first episode of Scooby-Doo actually set on Halloween, "The Headless Horseman of Halloween" and its titular Headless Horseman didn't make my scariest Scooby villains list, but it still an episode worth watching or re-watching for any Scooby-Doo fan. It's like "Nowhere to Hyde" in that its another episode that takes an old scary story and places it into the show's lore as a true legend. At a Halloween party with the descendent of Ichabod Crane from Legend of Sleepy Hollow fame, the gang run into the pumpkin headed ghoul who cries out "I want a head." The Horseman's headlust reaches its peak when he chases down the Crane descendent girl's cousin on horseback into the fog and re-emerges with the cousin's head on his shoulders (I'll let you figure out that twist yourself). The episode is a standard episode of Scooby-Doo in most regards and doesn't really lean into its Halloween setting for much more than a premise, but its reinterpretation of one of American horror's oldest icons into its lore is another fun example of how the show perpetuated macabre cultural artifacts into public consciousness on its journey to become itself a cultural artifact.