TV Halloween episodes and specials herald the arrival of America’s three-headed holiday season, where we get super happy, super spendy, and super hungry before a long, dark winter.
To help jump-start the season, we’re recommending five of the best Halloween episodes of TV shows like The Simpsons, South Park, Trailer Park Boys, The Office, and Freaks and Geeks. We even tossed in a couple of classic Halloween TV specials—and a few words from Freaks and Geeks’ Mr. Rosso, Dave “Gruber” Allen.
7. The Simpsons | “Treehouse of Horror V” (S6, E6)
It’s too bad that “Treehouse of Horror V” wasn’t the sixth Simpsons Halloween episode since it’s also the sixth ep of the sixth season. Oh, well—665 is still pretty close to the Holy Number.
In the fifth edition of the series’ perennial Halloween episode, The Simpsons’ writers drop the family into three stories:
- “The Shinning,” where Homer loses his mind while caretaking Mr. Burns’ estate for the winter. (Best line: “No beer and no TV make Homer go something, something.”)
- “Time and Punishment,” where Homer turns a toaster into a time machine, leading to nightmarish scenarios—including a world without donuts!
- “Nightmare Cafeteria,” a gorefest where the students become the meat in Lunchlady Doris’s “Sloppy Jimbos.”
Kinda gory, genuinely creepy in spots, and totally hilarious, “Treehouse of Horror V” is a Halloween special we watch annually.
Stream The Simpsons on Disney+.
6. The Paul Lynde Halloween Special
This wonderfully strange Halloween special (an exercise in contract-fulfillment for Lynde) features guests like the Wicked Witch of the West (Margaret Hamilton, reprising her role from The Wizard of Oz), legendary rock band Kiss, and the dear, departed Betty White. It also has Mormon luminaries Donny and Marie Osmond dressed in devil costumes!
The loose variety-show narrative has Lynde hating Halloween but agreeing to do some PR work for the Wicked Witch, Witchiepoo (from H.R. Pufnstuf), and White, the good witch.
In between, Lynde (as a trucker) marries Pink Tuscadero from Grease and cracks some very naughty jokes (for the time), Kiss mimes its way through three wildly out-of-place songs, and the cast performs “Disco Baby.”
Unfortunately, the special was nearly lost, and the only surviving copy looks like a potato-quality VHS recording.
Watch The Paul Lynde Halloween Special free on YouTube or rent it from Amazon Prime Video.
5. Trailer Park Boys | “Halloween 1977” (S6, E5)
It turns out that Trailer Park Supervisor and ex-cop Jim Lahey wasn’t always a stumbling, incontinent drunk—and he was a competent officer. That is, until Halloween 1977.
In this episode, Lahey finds a film reel. The footage proves that Halloween shenanigans by Ricky, Julian, and Bubbles led to Lahey’s firing from the Sunnyvale police force. “Mr. Lahey was nice back then, and we turned him into a drunk lunatic,” Bubbles says when confronted about the revelation.
The episode doesn’t feature your favorite TPB characters in funny costumes, but it sets up the hilarious finale of this fan-favorite season. So maybe also watch Episode 6: “Gimme My F**king Money or Randy’s Dead.”
Stream Trailer Park Boys on Netflix.
4. South Park | “Pink Eye” (S1, E7)
What’s more transmissible than the zombie virus? That’s right: pink eye, which we all—South Park included—treat like zomb-unctivitis, anyway. And what a way to subvert the “Oh my god—they killed Kenny!” gag.
Other notable gags in this classic episode include Stan as a Raggedy Ann–less Raggedy Andy costume (a slight dig at couples’ costumes) and Cartman as Adolf Hitler. We can’t believe they got away with the latter in 1997.
Stream South Park on Max™.
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3. It’s the Great Pumpkin, Charlie Brown (1966)
It might be 57 years old in 2022, but this Peanuts-gang adventure holds up.
This time, Charlie Brown somewhat cedes the loser role to his blanket-toting, thumb-sucking buddy Linus.
Linus believes that a gigantic pumpkin delivers presents on Halloween night. Obviously, this is total b.s. (everybody knows that loot delivery is Santa’s job), and the Peanuts gang tells Linus so. They all go trick-or-treating while Linus sets up camp in the GP’s drop zone: a punkin patch, natch.
If you’ve yet to see this Halloween gem, we won’t spoil the ending for you. Just watch it already.
Stream It’s the Great Pumpkin, Charlie Brown on Apple TV+.
2. The Office | “Halloween” (S2, E5)
In the first and best The Office Halloween episode, Dunder Mifflin boss Michael Scott is dropping the ball again. He was supposed to let one DM employee go by October 31, and, bless his poor tender heart, Michael can’t bring himself to swing the axe.
The rest of the show is classic The Office—highly relatable workplace annoyances and coworker idiosyncrasies—but with silly costumes. And we’re here for it, especially with Michael trying to pick a head to roll while wearing an extra cabeza made of papier-mâché.
Stream The Office on Peacock.
1. Freaks and Geeks | “Tricks and Treats” (S1, E3)
This episode of the beloved late-90s comedy-drama Freaks and Geeks nails one of the saddest moments in a kid’s life: realizing you’re too old to trick-or-treat.
It also shows a similar moment in the lives of older teens, who are both too old and too cool to participate in Halloween. Except, you know, for raising a little hell.
That’s how Lindsay Weir (Linda Cardellini), Nick Andopolis (Jason Segel), and friends came to smash their high-school counselor’s jack-o’-lantern. “Oh, man,” says Jeff Rosso (Dave “Gruber” Allen). “That is so uncool.”
We agree. And, as usual, Mr. Rosso has everything in perspective. What does he think about the pumpkin prank 23 years later?
“I think, in Mr. Jeffrey Theodore Rosso’s mind, not being cool makes you cool in some ways,” Gruber tells CableTV.com. “But then sometimes there are things people do that are just uncool!”
Stream Freaks and Geeks on Hulu or Paramount+.
In a scene from the Freaks and Geeks episode “Tricks and Treats,” high school counselor Jeff Rosso (Dave “Gruber” Allen) watches students speed off after they smashed his jack-o’-lantern.
