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Meme History: Halloween Memes

Be afraid, be very afraid. Just kidding! We’re here to laugh.

Photo of Kyle Calise

Kyle Calise

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In each edition of web_crawlr we have exclusive original content every day. On Saturday our Video Producer Kyle Calise explores the origins and history of the most iconic memes online in his “Meme History” column. If you want to read columns like this a day before everyone else, subscribe to web_crawlr to get your daily scoop of internet culture delivered straight to your inbox.


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Halloween: It’s a moment for bait and switchessweet nothings that taste good and melt away in your mouth in 5 minutes, scary things, and spooky cozy fall affectations

Today, we’re bringing you not just one, but five of our favorite Halloween memes of all time.

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5) Art The Clown

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Our number five pick is a product of a perennial Halloween scare-trope: clowns. 

Originating as far back as 2008, Art the Clown didn’t make his meme debut until after the 2022 horror/slasher film, Terrifier 2

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But what separates Art from other clowns is also the thing that makes him great meme-fodder—he’s a super awkward-looking, and generally kind of lurky dude.

Although the film was reportedly scary enough to make moviegoers throw up and pass out in theaters, online, Art is emblematic of someone’s social clumsiness. His memes are used to punctuate any situation where someone stands out like a sore thumb, and has fully internalized their weirdness, or if someone or something is just being a little too extra.


4) Scooby-Doo

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Number four comes from a piece of media far less scary, more of a classic, and far lighter: Scooby-Doo.

Although the Scoobyverse manifests online as any number of memes, from “Shaggy This Isn’t Weed,” to “Scooby-Doo Punching Fred,” to “Are you Challenging Me?” by far the most famous one comes from the trope that at the end of every episodethe villain is unmasked.

It’s a classic subject-object meme—but rather than saying something is better than something else, memers often leverage this classic cartoon moment to say something is or is like something else. 

Typically, this is just plain old fun, although like most image macros, depending on how hard the user wants to go, it can be used to comment on subject matter of more or less importance to the real world.


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3) Miserable Michael Myers

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Coming in at number three, we have the eternal Michael Myers.

Specifically, Miserable Michael Myers. This alliterative meme originated in a video from a since-deleted Instagram post, of a child wearing a Michael Myers mask in the backseat of a car, in October of 2018.

Pretty much immediately famous on Instagram and Twitter, as you might expect this image macro crops up whenever a memer has a moment of disgust, despair, or well, misery. It often appears in a situation that’s both mundane and totally relatable


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2) Spirit Halloween

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Our next pick has less to do with terrifyingly vacant expressions on the face, and more to do with vacant retail space.

Spirit Halloween is your favorite seasonal costume store, usually taking over the sad empty space in your local strip mall for two or three months in early Autumn each year. On October 19th, 2019, the Facebook page “Post Ironic Meme Vault” uploaded this image of a fake Guy Fieri Halloween outfit made to look like one of the countless pre-packaged costumes sold en-masse by Spirit Halloween.

Within a few years, an easier-to-manage template began circulating all over Reddit, ImgFlip, and wherever you get your memes. 

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It’s actually great. Because all in one easy-to-use meme, users get a sassy headline, room for color text, and a huge blank space for an image of the thing they want to poke fun at. And the possibilities for this are endless.


1) Dwight Schrute Pumpkin Head

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And finally, no list of hallomemes could possibly be complete without our top-favorite: “Dwight Schrute Pumpkin Head.”

The Office’s Season 9 Halloween episode “Here Comes Treble” features a subplot wherein Dwight “decided to really get into the spirit of Halloween.” To that end, he puts a carved pumpkin on his head, which gets stuck.

The earliest known image macro was posted to Pinterest in 2012, and features a simple Dwight quote from the episode, but its renown has since grown. This one has become a general stand-in for mid-fall lovers the internet over.

If Christian Girl Autumn is the fall meme for those of us who are just into being cozy, then Pumpkin Head is for everyone who’s less about being perfectly aesthetic and more about giving general spooky season vibes

So there’s our top five, but in fairness, honorable mentions have to go to Hubie HalloweenWerewolf Bar MitzvahLoabMomoGrimace, and Slender Man

We could keep going, but at a certain point we need to let you get to your costumes, your candy, and of course, your hallomeme-posting.

Stay spooky everyone.


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