The Simpsons celebrates two major milestones with its Oct. 16 episode. It’s not just the 27th installment in the series’ ongoing Halloween anthology, “Treehouse of Horror” — it’s also the show’s 600th half-hour. After its debut, “Treehouse of Horror XXVII” will live alongside the other 599 episodes at Simpsons World, the show’s streaming home powered by FX’s on-demand arm, FXNow. Among the tricked-out special features of Simpsons World is the ability to assemble playlists of episodes and clips of your own choosing, like, say, the Top 10 “Treehouse of Horror” segments. As inspiration for your own deep dive into the ghosts of “Treehouses” past, here’s how we would assemble such a list. And while you need to be an FXNow subscriber to be able to access the many delights of Simpsons World, civilians do get an hour-long preview pass, which is just enough time to stream all 10 of these six-to-seven minute funny-spooky stories.
10) “It’s the Grand Pumpkin, Milhouse” (“Treehouse of Horror XIX,” 2008)
The Simpsons takes aim at the Halloween classic, It’s the Great Pumpkin, Charlie Brown — which celebrates its 50th birthday this year, by the way — and hits the pumpkin-shaped bull’s-eye. The innocent Great Pumpkin of Linus’s dreams becomes the stuff of Milhouse’s nightmares, as the Grand Pumpkin realizes what’s being done to gourd-kind and sets about inflicting the same punishment on mankind. Like a vintage Peanuts special, this story has a moral: Do unto holiday symbols as you would have them do unto you.
9) “Bart’s Nightmare” (“Treehouse of Horror II,” 1991)
Bart and Homer have always had a contentious relationship, but the pair finds that elusive common ground after the son transforms his father into a jack-in-the-box. Where most “Treehouse” segments run toward the gruesomely hilarious, “Bart’s Nightmare” has a sweetly emotional center. No wonder this particular dream causes feelings-avoidant Bart to wake up screaming.
8) “Attack of the 50-Foot Eyesores” (“Treehouse of Horror VI,” 1995)
Homer’s love of doughnuts lands him in hot water — or should that be, hot d’oh? — with another giant doughnut fan: Lard Lad. The towering cherub-cheeked mascot proceeds to stalk the Springfield landscape, making the town’s citizens both angry and hungry.
7) “The Island of Dr. Hibbert” (“Treehouse of Horror XIII,” 2002)
Thanks to this Island of Dr. Moreau homage, we no longer have to wonder what the Simpsons family’s spirit animals are. And it’s worth noting that they’re more adorable than scary in their animal form. Who wouldn’t want a plush Maggie the Anteater doll? Get on that, Simpsons merchandisers!
6) “The Terror of Tiny Toon” (“Treehouse of Horror IX,” 1998)
After years of cackling at animated violence, Bart and Lisa experience the true horror of what it’s like to be limb-tearing adversaries Itchy and Scratchy when they’re transported inside the ultra-gory cartoon-within-the-cartoon. Whatever suffering the siblings endured, they did perform a valuable public service by demonstrating exactly what happens when you stand in the line of fire of a piranha-filled water hose.
5) “Homer3” (“Treehouse of Horror VI,” 1995)
Released a month prior to the original Toy Story, Homer beat Woody and Buzz into the third cartoon dimension. Given a CGI makeover by the company that later became DreamWorks Animation, the Simpsons patriarch explores a digital landscape filled with concentric shapes on a Tron-like grid. Trust us, kids — back in the ’90s, this looked positively futuristic.
4) “The Devil and Homer Simpson” (“Treehouse of Horror IV,” 1993)
Holier-than-thou neighbor Ned Flanders is the devil? That’s the all-too-believable hook for another doughnut-themed horror show, where Homer willingly trades his soul for a sweet, sweet circle of fried dough. The segment winds up being a great showcase for the enduring strength of Homer and Marge’s marriage, not to mention a reminder of how much we miss Phil Hartman and his incompetent attorney, Lionel Hutz.
3) “The Shinning” (“Treehouse of Horror V,” 1994)
Stephen King’s horror classic gets a Scottish twist, courtesy of Groundskeeper Willie, who rides to the rescue when a cabin fever-afflicted Homer goes after the rest of his family while locked inside Mr. Burns’s cavernous house. There have been many “Redrum” gags over the decades, but the one in “The Shinning” remains the gold standard.
2) “The Raven” (“Treehouse of Horror I,” 1990)
A direct adaptation, rather than a spoof, of Edgar Allen Poe’s immortal poem, “The Raven” is light on jokes but rich in style. The segment finds the animation team pushing the boundaries of what the still-young show was capable of, while Dan Castellaneta gets an early opportunity to tap into Homer’s range of emotions. Simpsons producers have since said that they’d never attempt something like “The Raven” again, which makes it even more of a rare bird.
1) “Citizen Kang” (“Treehouse of Horror VII,” 1996)
Even if this weren’t an election year — and one involving a Clinton, no less! — “Citizen Kang” would easily climb to the top of our “Treehouse” list. A hilariously on-point critique of America’s democratic process, it’s also the finest hour of everyone’s favorite alien visitors, Kang and Kodos. All hail President Kang … even though we totally voted for Kodos.
All episodes of The Simpsons are available to stream on Simpsons World.