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10. Treehouse of Horror 14
A kinda meh Frink story aside, this is a great collection, and well worthy of a spot in the top 10. Homer taking up the mantle of the Grim Reaper, and trying to fool God, is as hilarious as it is dark. Milhouse and Bart getting a watch that stops time is perhaps the least scary Halloween story to date up to this point, but it still makes for a genuinely intriguing plot based around Bart's subservient blue-haired best friend Fun fact: This is also the first Treehouse of Horror to use a "Treehouse of Horror" title card in the actual episode – and it's painted with Homer's blood.
9. Treehouse of Horror 18
Treehouse of Horror 18 is a love letter to the show's past. Not only is it a fitting tribute to The Simpsons Halloween canon, with neat spins on well-established narratives, it has some fantastic references for long-time fans of the show, too. The Kodos/Homer shower scene is awkward as hell and you'll be laughing throughout, "Mr. and Mrs. Simpson" is a parody that lets the action and Marge's chemistry with Homer do the talking, and "Heck House" is joyfully anarchic, finally shining a spooky light on Springfield's kids. Don't let the season number fool you, this is just as good as the classics.
8. Treehouse of Horror 15
Treehouse of Horror 15 is the best Simpsons Halloween episode in the last 20 years. It's a sorry state of affairs that over half the show's output has been relegated to constant comparisons to its older, funnier brother, but this entry proves it still has jokes and scary scenarios in abundance. Flanders steals the show with his futile attempts to stop Homer from dying; the Jack the Ripper parody has enough of that sweet, sweet Simpsons flavour to keep it fresh, and Homer *ahem* entering Mr. Burns through a shrunk-down ship is just as joyfully silly as you'd imagine.
7. Treehouse of Horror 2
God bless Bonerland. The second serving of Treehouse of Horror mines its Twilight Zone influences to good effect as Bart's mind-bending powers steal the show with multiple alternative history test answers about the good ol' US of A. Homer's misuse of the monkey paw is only made funnier by the kicker that his last wish being a turkey sandwich, one that he curses for being a little dry. Oh, the humanity. Mr. Burns' robot slave story, though, is barely played for laughs and stops this episode from cracking the top five.
6. Treehouse of Horror 4
While "Bart Simpson's Dracula" and "Terror at 5 ½ Feet" rarely stray away from tried and tested material – including a William Shatner Twilight Zone episode – it's Homer's deal with the Devil that generates the most laughs and raises it from a very good Treehouse of Horror to an outstanding one. It certainly stakes (ahem) a claim for the best one-shot Halloween story in the show's history; Flanders as the Devil is a genius concept and the animation – including the Devil's Fantasia-style flourish – is up there with the show's very best. Phil Hartman's Lionel Hutz, though, steals the show. He's at his most brilliantly incapable here – and proves the format works best when it leans on Springfield and its characters rather than real-world horror influences.
5. Treehouse of Horror 7
The best seventh instalment of a beloved franchise since Rocky 7: Adrian's Revenge, Treehouse of Horror 7 does away with its framing device altogether to craft an episode packed with some of the show's best, most ghoulish work. Misdirection a-plenty is the name of the game with both "The Thing and I" and "The Genesis Tub" but, while they both provide irony and scares in equal measure, it's Kang and Kodos' first full short in years that ranks as the high point. Filled with one-liners that are still used today, and a genuinely funny commentary on American politics, "Citizen Kang" is worthy of appearing on Treehouse of Horror's Mount Rushmore.
4. Treehouse of Horror
The original Treehouse of Horror, if not quite the best, still stands the test of time – and then some. "The Raven," is, for my money, the definitive version of Edgar Allan Poe's poem. Elsewhere, "Bad Dream House" is a bit tame by later standards but features some delightfully spooky imagery and one of the show's greatest jokes: a haunted house that would rather implode than live with The Simpson family. The debut of Kang and Kodos is also wrapped up in a nice bait-and-switch story, in what would prove to be a longstanding Treehouse of Horror tradition.
3. Treehouse of Horror 10
I know, I know. Putting something from post-season 10 this high up the list may amount to sacrilege for many a Simpsons stalwart, but Treehouse of Horror 10 deserves it. Being one of the most consistently fun (and funny) episodes isn't enough for you? There's Homer accidentally spilling the beans on Ned's death, a madcap Y2K story, and a campy comic book caper to boot. All in all, this well-rounded anthology proved The Simpsons hadn't missed a step in the Halloween department as its lustre began to fade.
2. Treehouse of Horror 6
The sixth Treehouse of Horror not only had some of the most inventive imagery found in any Halloween spin-off, it carries with it a playful, brighter tone that puts it head and shoulders above most episodes, old and new. "Attack of the 50ft Eyesores" and "Homer3" showcase Homer's selfish arrogance in a way that sees him get an entertaining comeuppance and, in case you thought things were getting too light, Groundskeeper Willie's there to give you the heebie-jeebies in a Nightmare on Elm Street homage. This episode is, Halloween or otherwise, a classic. It even comes with some great advice: "Do not touch – Willie."
1. Treehouse of Horror 5
Simply put, this is the best Treehouse of Horror. The love and care put into "The Shinning," with its litany of Kubrickian nods, would ordinarily be enough to elevate it to greatness on its own. Beyond that, every story is filled with belly laughs and increasingly gory deaths. Groundkeeper Willie's trio of axe-related murders will still make you laugh over 25 years later, as will Moe playfully poking at his brain matter, Homer leaving Grandpa at the gas station, Skinner's groan-worthy murderous puns, and much, much more besides that. If you watch this and don't think it's the best, I owe you a Coke.
