Ten of the Weirdest Paintings in the History of Art

Maria Cristina
10 min readApr 1, 2022

Happy April Fools’ Day! To celebrate the silliest holiday, I’ve decided to share some of the weirdest and most bizarre paintings I’ve encountered in the history of art.

Truth Coming Out of Her Well
Source: Wikimedia Commons

1. Truth Coming Out of Her Well by Jean-Léon Gérôme

All of the paintings I’m going to talk about today are weird; however, I have to say that this painting is particularly strange. Truth Coming Out of Her Well is an allegorical paintings that depicts truth as a naked woman climbing out of a well. The piece is based on a quote from the philosopher Democritus: “Of truth we know nothing, for truth is in a well.” In Gérôme’s vision of the saying, Truth carries a whip “to chastise mankind.” The image of a naked woman climbing out of a well is pretty absurd on its own, but her ridiculous expression is what really makes this painting so goofy. I mean, look at that face, it’s so memeable!

Saint Lucy
Source: Wikimedia Commons

2. Saint Lucy by Domenico Beccafumi

In Christian tradition, Saint Lucy is a third century martyr who endured a rather gruesome death. During her martyrdom her eyes were torn out, although some sources say her sight was miraculously restored before her death. Because of this, she is the patron saint of the blind, and is commonly associated with eyes and eye trouble. In Domenico Beccafumi’s painting of the saint, she is pictured carrying her own eyes in a dish, which is obviously extremely weird. Strangely, she also has eyes in her head, so it’s just a bizarre image. Although, I’m guessing no one wants to paint a woman with big bloody holes in her face, so I guess that makes sense.

As weird as it seems, the eyes in the dish is actually a pretty common attribute in paintings of Saint Lucy. I also think this painting is particularly strange because Saint Lucy doesn’t have any eyebrows-which gives her a pretty strange expression-but the extra set of eyes is definitely the most bizarre part of this painting. If you’re interested in Saint Lucy’s extra set of eyes, I recommend you check out this article titled “I’m Obsessed with Saint Lucy’s Extra Set of Eyes in This Renaissance Painting” to learn more about her iconography.

Portrait of Antonietta Gonzalez
Source: WikiArt

3. Portrait of Antonietta Gonzalez by Lavinia Fontana

Looking at this painting for the first time, you’d probably assume it’s an image of a character from a fantasy novel. The first time I saw it, I certainly thought the artist intended some kind of joke. However, Lavinia Fontana’s Portrait of Antonietta Gonzalez actually portrays a real person. Gonzalez suffered from hypertrichosis disease, which causes an abnormal amount of hair growth over the body. Because of her unusual condition Gonzalez and her family (several of whom suffered from the same condition) lived in the court of King Henry II of France, where they participated in social events and entertainments.

Italian painter Lavinia Fontana painted the little girl when she was less than ten years old. In the painting, Gonzalez wears an elaborate court dress and holds a piece of paper that details her life story. It’s a particularly interesting painting because Fontana goes beyond painting Gonzalez’s disease. Instead, the artist portrays the child as a fully realized human being. The portrait captures the little girl’s sweet and charming demeanor while also accurately portraying her disease. It is a nuanced piece that manages to give its subject personality without shying away from the reality of hypertrichosis.

Portrait of Eve
Source: WikiArt

4. Portrait of Eve by Giuseppe Arcimboldo

Okay, this 👏 painting 👏 is 👏 so 👏 weird! In case you’re wondering, yes, this is a picture of a woman with a face made out of human bodies. Bizarre? You betcha.

As unconventional as this portrait is, there’s actually some logic behind the artist’s choice. The Eve in this painting is the Biblical Eve (notice the apple she holds), the first woman and the mother of all humankind. Therefore, the bodies that make up her face represent the innumerable human descendants that trace their lineage back to Eve. In this painting, her body is literally composed of all the bodies produced by her bloodline. You could say that Eve has all of humankind within her flesh. It’s an interesting artistic choice.

Giuseppe Arcimboldo, the artist behind Portrait of Eve, is rather famous for his composite portraits, in which human faces are constructed from objects like fruit, books, and even fish. His art is utterly unique in the story of Western painting, and, as such, it’s notoriously difficult to interpret. However, I think it’s safe to say that it’s wildly entertaining and charming. Or, at least, it’s normally entertaining and charming. Maybe it’s the naked people that grabbing on to Eve’s hair band, but I actually find this painting kind of disturbing. Looking at it too long makes you a little queasy in my experience. However, if you’re still up for more weird art, there’s a matching painting of Adam created in the same bizarre style.

The Art of Living
Source: renemagritte.org

5. The Art of Living by René Magritte

If you’re like me, you’re probably screaming at your screen “what is going on with his head?!” Is it a balloon? Is it a giant orange? Is it some kind of bizarre basketball? The answer is unclear, but whatever you see in this painting, I think we can all agree it’s very weird.

Granted, The Art of Living was created by a Surrealist artist, which means that the viewer should expect some degree of weirdness. Magritte was known for his bizarre and witty paintings, and his work often challenges viewers by placing everyday objects in strange contexts. The contradictions in his art force viewers to examine their understanding of the world around them.

All the same, The Art of Living is especially weird because most of the painting looks fairly realistic and normal, aside from the huge, abnormally orange head! My reading of this painting is that the large head implies that the self is a small part of a larger world or larger consciousness. The phrase “the art of living” refers to the need to expand your mind or worldview. But, what do I know? It could just be a portrait of a guy with a really big head.

Escaping Criticism
Source: Wikimedia Commons

6. Escaping Criticism by Pere Borrell del Caso

I know that this blog is all about weird paintings, but this piece is more comical than weird. Pere Borrell del Caso’s masterpiece Escaping Criticism is a trompe-l’oeil to be remembered. The piece depicts a young boy climbing out of the frame of the painting. The piece is so well executed that it’s hard to believe that you’re looking at a two dimensional piece of art. The interpretation of this piece is debated, but many art historians believe that Borrell del Caso was commenting on the difficulty of being a Realist in the age of Romantic art.

Trompe-l’oeil means “deceives the eye,” and that’s certainly what’s going on in this piece. I don’t know what criticism the boy in Borrell del Caso’s masterpiece is escaping, but he’s certainly doing it very realistically.

Cat with Cat Necklace (Source: Pixels)

7. Cat with Cat Necklace by Louis Wain

Louis Wain was an artist of cats, a fact that endears him to me because I’m a cat person if there ever was one. Wain became famous for his drawings and paintings depicting cats engaged in everyday activities.

However, as he grew older, Wain began to suffer from mental health issues (some modern scholars believe he was schizophrenic), and his art changed accordingly. His later work is much more colorful and experimental, and some of it has a distinctly psychedelic vibe.

Wain’s Cat with Cat Necklace feels like something out of an Alice in Wonderland themed nightmare. It depicts a colorful cat with a stylized, geometric face. In a way, it reminds me of a mandala design. However, the actual look of the cat is more reminiscent of an Elizabethan portrait. Looking carefully, you can see that the cat wears a wide, elaborate ruff and chain of office along with a fancy headdress. I don’t know how to interpret this piece and all its visual elements, but it’s certainly very cool. To my mind, it has big acid trip energy (not that I have any personal experience with that), but in a positive way. I particularly like the cat necklace.

The Garden of Earthly Delights
Source: Wikimedia Commons

8. The Garden of Earthly Delights by Hieronymus Bosch

The Garden of Earthly Delights is the quintessential weird painting in the history of Western art. It is full of bizarre and inexplicable little vignettes that have become meme fodder around the internet. Seriously, if you see a painted image that makes you say “what?!” on the Internet, there’s a good chance it comes from The Garden of Earthly Delights.

Detail from the Garden of Earthly Delights

The painting is incredibly complex and detailed. I’ve seen it in person, and I can tell you that you’d need to stand in front of it for a long time to actually look at everything that’s going on in the piece. My theory about The Garden of Earthly Delights is twofold. One, I think that the artist-Hieronymus Bosch-was having a grand old time thinking of strange things to include in the piece, and clearly he wanted to entertain viewers of the piece as well. However, I also think Bosch was operating in the established tradition of fantastical and bizarre Medieval Hell imagery as well as the equally bizarre tradition of Medieval marginalia. Both of these motifs were on their way out by the time Bosch created The Garden of Earthly Delights, but a penchant for intricate detail survived much longer in Northern Europe than in other parts of the continent.

Detail from the Garden of Earthly Delights

Thus, you can now look at The Garden of Earthly Delights and enjoy images like a pair of ears carrying a knife, a bird eating a human, a man embracing a giant owl, and one really strange looking giraffe. As Crowley, one of my favorite characters from Neil Gaiman and Terry Pratchett’s delightful novel Good Omens, once said: “That Hieronymus Bosch. What a weirdo.”

Ya tienen asiento
Source: Brooklyn Museum

9. Ya tienen asiento (Now they are sitting well) by Francisco Goya

I like to think of this etching as The Lampshade People, however, its proper name is Ya tienen asiento, which roughly translates to Now they are sitting well. The piece depicts a group of young women wearing their petticoats upside down and balancing chairs on top of their heads. The piece is meant to be satirical; the chairs on the heads imply that the women are thinking with their bottoms, not with their brains.

The piece comes from Francisco Goya’s Los Caprichos series, which criticizes the social ills and superstitions of contemporary Spanish culture. The two young women in Ya tienen asiento are blindly following fashion, despite the onlookers laughing at them. However, to me, they will always be two sentient lampshades carrying chairs, and, of course, they have to carry them on their heads because lampshades don’t have arms. That’s just my logic.

Snail Cat
Source: British Library

10. Snail Cat

There’s a whole meme genre based on the absolutely crazy images of cats that Medieval artists created ( I present exhibit A). Medieval artists seemed to take great pleasure in adding funny little scenes to the margins of illuminated manuscripts, and, like many modern social media users, they found that nothing is more ridiculous and humorous than a cat. (These illustrations in the margins are called marginalia, and you can read more about them here if you’re interested.)

The marginalia often had nothing to do with the actual text of the manuscript, which meant that this liminal artistic space offered a rich opportunity for creative expression. Snail cat is my favorite example of this bizarre art form. This illustration of a cat in a snail shell may look totally out there at first glance, but, as I mentioned earlier, it’s actually one of many preposterous Medieval images of cats. The drawing is also part of a larger Medieval obsession with snails. Snails are one of the most popular motifs in Medieval marginalia. They can be found in all sorts of manuscripts, jousting with knights, climbing ladders, and answering prayers. You know, just normal snail stuff. No one really knows what the snails meant to Medieval people, but they were clearly an important symbol. I look at snail cat as a combination of the greatest hits of Medieval marginalia. In this picture, you get two bizarre things for the price of one.

Snail cat comes from the Maastricht Hours, an illuminated devotional manuscript produced in the Netherlands during the early fourteenth century. In my opinion, snail cat is not the hero we deserve, but he is the hero we need.

With that being said, I’m going to take a break from writing about ridiculous art for a while.

Originally published at https://artisthesolution.blogspot.com on April 1, 2022.