13 Vintage Halloween Photos That Will Haunt Your Dreams

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It’s been said that reality can be more terrifying than any dark daydream from the sharpest Hollywood mind. Having combed through some pretty darned terrifying vintage pics, we tend to agree.

So without further ado, here are some of the weirdest, wildest, and most disturbing vintage Halloween photos…direct from (believe it or not) real life. Pleasant dreams!

(NOTE: We weren’t able to locate original sources for several of these pics. If you own them, please tell us. We’d like to credit you!)

Aww. What a Cute Little Monster

What’s REALLY creepy is that a toddler sat still this long. Was she promised something? No more suffocating devil masks if she promised not to make any sudden moves?

He’s Coming for You

halloween child skeleton in costume

The blur of whatever that is in this chilling child’s hand and the position of his or her legs shows this little creature of the night has something on its mean little mind…and it probably isn’t candy. Run.

Such a Good Mom

man dressed as a doll for Halloween

We have it on semi-reliable authority (sorry, that’s the best we could do) that this is a man. That part is fine (and fun), but the doll? Dude.

He Promises He Won’t Tell

…if they’ll just let him go. We wonder how this wound up, but at the same time, we’re not so certain we want to know.

Poor Little Dolly

And we don’t just mean the plastic one. This photo haunts our imaginations in so many ways. The heart-wrenching poverty, the starkness, the weird mask…reality truly can be more frightening than fiction.

We…Just Can’t

Another “send help” pic, but this time you can see the dejected expression. You know it’s an eerie pic when the most daunting image is the face that ISN’T masked.

Not the Disney ‘Cars’ You Imagined

Awww, so adorable, the little masked grins, the hand-holding, the…burning vehicle in the background?


We don’t know who actually owns this photo, but it pops up everywhere with the reference “circa 1940s” and still gives us the chills 80 years later. You have to wonder whether she always led them around that way, not just on Halloween.

The Big Guy Downstairs

No comment.

The Scariest One

…is the little girl. What the unholy heck is she smiling about? We wonder how many of her little friends from this pic actually made it home that night.

That’s Ducked Up

Just no. That is all.

Air Time

How did this even happen?

At Least They’ve Got Each Other

Some people just get lucky.

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