These Creepy Halloween Photos Date Back to the Mid-20th Century

Two people stand side-by-side wearing large, hand-drawn paper bag masks over their heads and plaid flannel shirts.

These unsettling mid-20th century photos of kids in Halloween costumes are bound to bring a few memories — or nightmares — for viewers.

Coming from the spectacular snapshot collection of Robert E. Jackson, the photos capture creepy costumes, pumpkin heads, and even a clown baby.

“The way I acquire my photos is through eBay, Instagram, Facebook, people offering me images, and traveling to shows,” Jackson tells PetaPixel.

“I like photos which are detached from their original narrative. Thus, I am not a subject-based collector per se. I am really not interested in the history behind the photo, but rather I am more drawn to how the image strikes me emotionally. I like photos of mystery, and Halloween photos, to me, contain lots of mystery.”

A man in a plaid shirt sits in a chair holding a baby wearing a clown mask and a pointed hat.

A child wearing a large, flat clown mask and costume stands in a living room next to a striped armchair.

Two young girls wearing matching plaid dresses and masks stand side-by-side in front of a chair.

A child stands in front of a log, wearing a carved pumpkin as a mask over their head.

Flashbak notes that a lot of mid-20th century costumes depicting cowboys, cowgirls, Disney characters, Casper the Friendly Ghost, the Lone Ranger, and Woody the Woodpecker were produced by now-defunct companies like Ben Cooper, Inc., Collegeville Flag and Manufacturing Company, and H. Halpern Company (Halco).

No doubt at the time it was all a lot of fun, but viewed through today’s lens, a combination of the cheap plastic outfits, the direct flash, and the passage of time makes it seem like the photos are behind-the-scenes shots of a horror movie.

A young girl in a light-colored dress and a plain white mask holds a small carved pumpkin while sitting in a chair against floral wallpaper.

A child stands on a lawn in front of a house wearing a round, fabric pumpkin costume with a matching hat.

The photographs echo Halloween’s roots, which lie in the ancient pre-Christian Celtic festival of Samhain, a feast to mark the death of the old year and the birth of the new.

It was believed that on this night the veil separating the worlds of the living and the dead grew thin and ruptured, allowing spirits to pass through and walk unseen but not unheard amongst men.

With the spread of Christianity, the traditions surrounding Samhain gradually became intertwined with Christian observances. All Saints’ Day, celebrated on November 1, honored saints and martyrs, while All Souls’ Day, on November 2, was dedicated to praying for the dead. The evening before All Saints’ Day became known as All Hallows’ Eve, eventually shortened to Halloween.

Children and the poor often masked or in outlandish costumes wandered the night begging for ‘soul cakes’ in exchange for prayers, and fires burned to keep malevolent phantoms at bay.

A child in a black cat Halloween costume with a mask and a shirt labeled "Jingles" stands with arms raised, holding a pumpkin bucket.

A child sits on porch steps wearing a paper bag mask with a hand-drawn face, holding a carved jack-o'-lantern.

A child stands in a living room wearing a dragon mask and a costume featuring a large dragon illustration, with a vintage television set visible in the background.

A person wearing a paper bag mask with a hand-drawn face and a plaid shirt stands in front of a wooden fence.

Either way, Jackson’s collection of ephemera, often called found photography or vernacular photography, is an excellent insight into the ordinary mid-century Halloween celebrations.

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