The 10 Creepiest Vintage Halloween Pics…Ever

 

At Halloween Alliance, we LOVE creepy. But when we researched vintage Halloween images, we got a little more than we bargained for.

Come along with us on a spooky journey into a much darker past than you may have imagined. But beware: when it came to preying on fears, kids weren’t spared anything in the good ol’ days. (Anything.)

Yeah…we’re going to go ahead and consider this an overprotective parenting fail. It doesn’t seem like those harnesses did a whole lot of good. But hell (sorry), at least they’re together, right? Forever…

Women: you’re probably okay. Men: run. Dear God, run. Save yourselves. That isn’t a Men’s Room, right? …right?

You can’t MAKE us say it. No. Seriously. You can’t. So just forget about it. We aren’t going to…Oh, okay, fine. What a cute little devil. Satisfied?

There really aren’t enough underwear changes in the world to get through just one viewing of this adorbs little vintage gem.

Yeah, we know. “Grownup doll” costumes are supposed to be peek-a-boo and flirty and adorbs and…not freakin’ terrifying. But…then there’s this. By the way, she’s (or is it a fella?) HOLDING a doll, too. And it’s…looking at her. We’re pretty sure of it. (Don’t go to sleep, lady…okay?)

That isn’t the car Michael Myers used to escape from the asylum, is it? We kind of think it is. We kind of feel worried right now. We’re kind of wondering whether this li’l guy ever saw 1959.

Sure, Halloween is all about hiding, but we’re wondering what “the teacher” (air-quotes, meaningful nod) is indoctrinating this masked little bunch into. And what she’s instructed them to unleash on the town while it’s peacefully sleeping in cozy beds.

We don’t remember the Black Death breaking out any time during the 20th century but just in case it were to pop up, these kids were ready. Plus, they had a sailor and some dude with a cone to help out in case…Okay, we’ve lost the plot on this one. Anyway…happy Halloween, strangely wrapped kiddies.

Isn’t it weird which one of these two is crying?

…but no one heard little Timmy’s whimpers in the night whenever the door creaked open, slowly, so very slowly, almost tauntingly, the soft snick, snick of the razor prickling his ears…nor did they seem to notice the hollow look in his eyes. But one day…yes, one day the town would come to regret…Be right back, we feel a movie plot coming on.

 

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