10 Creepy Medieval Paintings- Part 2

medieval paintings

I think everyone knows that many medieval paintings error on the side of weird. What I don’t think we realize is the treasure trove of oddities out there. I mean these painters were jacked up. I don’t know if they found ‘shrooms and consistently ate them while painting, but man! Anyway, my last 10 Creepy Medieval Paintings ranks #8 as the most read post, so why not give the people what they want? Let’s get started!

Medieval Drag Queen

drag queenMost drag queens are beautiful, all dolled up. Then you have Mark, to the left. Perhaps he hasn’t put his face on yet? Wait, I just realized something as I was typing this. How does Mark have boobs? Albeit not firm but seriously friends, what’s up with the boobs? I thought maybe this is just a super, super ugly woman but I think this is definitely a man. What do you guys think?




Medieval Sawmedieval saw

Ok, OW!!! Come on people! We don’t need to see that. You hear of the standard forms of torture but did they really torture people like this? Jesus! And did some ass hole really need to paint it? Why not a lovely bowl of fruit or flowers? This is some messed up Dexter shit right here.

the holy shatThe Holy Shat

Again, I’m questioning why one felt the need to document this and if this really didn’t happen, why imagine it up? Is she praying to his ass hole? Is she clapping? And actually now that I look closer, it’s almost like they are clapping in unison. Maybe this is a toddler and she’s trying to potty train him? Maybe he finally shits for the first time in the designated dirt hole the family uses for a toilet and she’s like “good job buddy!” Yes, I’d like to think this is a potty training moment.

weird monster Weird Monster

I’ve noticed there were monsters everywhere in Medieval paintings. They are walking through doors, at murder scenes, the lunch table….everywhere. This artist took it to a whole new level and put a monster on the monster’s ass. Then there’s a little boy next to the monster, happily flying what seems to be an airplane fashioned into a penis? This is so wrong.

On Drugsweird faces

There is no other way to describe this painting. I don’t even have to be a forensic historian (is there such a thing?) to know that this painter was on drugs. And he’s not even a good painter. I mean, look at the attention to detail in this pic versus Mark’s wrinkly boobs in the first one? Why are people’s faces on their torso? And why does it look like the thing on the left is holding a female urinal…and only has 1 eye? Bleh!

dildoDog Toys

This is as if the dog (I don’t know what kind of animal this is so we’re going with dog) ran off with someone’s dildo and the poor woman is trying to coerce the dog to “release”, in exchange for a nice fish. That dog’s probably like, “lady….I got all the fish flavor I need on this thing.”


With the exception of awful, disturbing is really the only other word to describe this painting. This type of monster is what nightmares are made of. But the artist was like, “it needs a playful quality.” He holds his paintbrush to his chin, pondering what delightful, light-hearted element he could add. And what does he settle on? Dead babies.


bird man


I’m pinching the skin between my eyes right now because I don’t know where to start. Is this a Halloween costume? Is this supposed to be a half-bird, half-man situation? I’m guessing those are titties and if this is a costume, why didn’t he put it inside the costume? And the bells around the waist and in the hands? I have SO MANY QUESTIONS! Was this what was funny back then? And he has I guess, a horn on his side? Like he’s gonna blow it upon entrance to the party and be like, “Hey bitches! I’m here!!!” Then shake his hips so his bells ring while simultaneously ringing the bells in his hands? SO. CONFUSED.


Magic Dick Ridewoman flying

This has to be an ad for adult toys. She’s like, “Purchase the rocket 3.0 and you too will feel like you’re on a magic dick ride!” And I know boobs have been a topic in several of these paintings but did the artist get the shakes when he was working on her tits? They look like icing bags that a baker just depleted. Or maybe she’s just deformed and the marketing budget only afforded Sally Sad Tits. We’ll never know.

weird manIncredibly Odd

Can you honestly come up with a better or more fitting title? I can’t. It does, however, remind me of Eeyore from Winnie the Pooh if Eeyore was on psychedelics and was an old man smoking. Like, what was the artist like that this actually came from his mind? Was he a genius or deranged? Personally, I think he was probably one sick puppy.

So yeah, that was my second installment of creepy Medieval paintings. I can confidently say that the artists of yesteryear did not disappoint. What do you guys think?


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