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When you think of old paintings, your mind may wander to an image with a somber, stiff tone. It’s likely because most of the surviving pieces are religious, creating an impression that this type of artwork often carries a serious vibe. 

What most people don’t see is the vibrant and humorous side, which you will see in the following images. They instantly break the impression of this supposedly restrained form of visual expression, making them extra funny

Check out this list to see what we mean, and as always, don’t forget to upvote your favorites!

#1

This Cat Has Seen Things

Old paintings showing a hilariously bad black cat with large yellow eyes and a white ruffled collar on a dark background.

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    #2

    Giving Your Cat Their Medicine

    Medieval old painting showing a person humorously interacting with a lion, highlighting hilariously bad old paintings.

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    #3

    What Is This?

    Medieval old painting of a musician with a lute riding a creature with a human face and trumpet-like nose.

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    In recent years, experts have begun challenging the “dark and gloomy” reputation that has long been associated with medieval art. In an article for The Conversation, academics José Alberto Moráis Morán and María Dolores Teijer Pablos began to dispel this notion by mentioning the colorful interiors of the Old Saint Peter’s Basilica in the Vatican City. 

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    #4

    This Painting Of An Absolute Unit

    Hilariously bad old painting of an oversized orange tabby cat standing on a bed in a simple room.

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    #5

    4-Year-Old Girl With Cat And Fish

    Old painting of a young girl holding a cat with an awkwardly funny expression and pose in vintage attire.

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    #6

    (Internal Dialogue) I'm Not Fat I'm Just Big Boned

    Old painting of a cat with exaggerated eyes and expression, showcasing hilariously bad art in a classic style.

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    According to Pablos and Morán, the original basilica, built around 326 to 333 AD on the orders of the Roman emperor Constantine, had large windows that made the entire space feel bright and airy. 

    The building also had marble mosaics and textiles, which ultimately proves that medieval architecture’s reputation for being “dark and sinister” was purely a myth.

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    #7

    This Dog Or Cat ?

    Old painting featuring a small dog with a humorous, awkward expression on a wooden floor in a historic setting

    I stumbled across this beauty today and needless to say, I like it’s eyes and lips.

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    #8

    Dog Treating A Bedridden Cat For "Melancholy" (Source Unknown, CA. 12th Century)

    Medieval style old painting depicting a creature holding a flask and a strange baby in a basket with a crab nearby.

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    #9

    "You Must Have Scared Him, Cupcake Is Usually So Friendly". St Martha And The Tarasque

    Medieval scene of knights and a woman battling a large creature, an example of hilariously bad old paintings.

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    “Many buildings of the early Middle Ages were painted in bright colours, though the passage of time has erased these fragile murals,” Pablos and Morán wrote. 

    As for artwork, both academics referred to the color restoration of the Amiens Cathedral in France. Pablos and Morán pointed out the “striking” shades of red and blue on the sculptures to prove that Medieval art was “colorful and lively.”

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    #10

    Saint-Lifard

    Portrait of a bishop in ornate robes holding a leash attached to a small dragon in old painting style.

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    #11

    "But This Is My Emotional Support Lobster!!" Said Gilbert, Defensively

    Medieval old painting of a rat with a humorous, crude style surrounded by colorful floral decorations and gold accents.

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    #12

    Spotted This Guy At The Gemäldegalerie In Berlin Last Year, He Looks Like A Grumpy Old Man

    Old painting of a cat with a human-like face sitting on a ledge, showcasing hilariously bad old paintings art style.

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    Some view Medieval art as odd, including author Olivia Swarthout. She even started a social media account aptly named “Weird Medieval Guys,” showing the peculiarities of the genre. As of this posting, the account has more than 600,000 followers (and counting). 

    “What makes them funny is often a juxtaposition of expression and situation, plus the medieval setting,” Swarthout told the Guardian in a 2012 interview, noting that her pieces are about giving something where people can say, “That reminds me of myself.”

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    #13

    Interesting Medieval Painting

    Medieval old painting depicting a comical figure balancing on bent legs while holding two shallow bowls.

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    #14

    Scheibler Armorial

    Medieval style old painting of a crowned cat with wide eyes sitting on a colorful abstract decorative background.

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    #15

    Welcome To My Delightful Spread

    Old painting of a cat with human-like expression standing on a table with food and kitchenware, showcasing hilariously bad art.

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    For Swarthout, it’s all about capturing the essence of the time period through its many imperfections, which she believes makes such images a hit with many people. 

    “There’s so much contained in this art – and particularly in the fact that a lot of it isn’t all that well-executed or approached with the artistic precision that we’re familiar with – that actually tells us so much about medieval life,” she explained.

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    #16

    This Cat Is A Mood?

    Old painting of a cat with oddly shaped face and tired expression, showcasing hilariously bad artistic style.

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    #17

    Perna (Oyster) - Miniature From Folio 108v From Der Naturen Bloeme (Kb Ka 16)

    Medieval old painting of a round creature with a beak, showcasing hilariously bad art that is actually brilliant.

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    #18

    Singing Angels

    Group of medieval singers with awkward expressions in an old painting showcasing hilariously bad art style.

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    #19

    Benedictine Monk With Wine As A Morning Drink

    Old painting of a cheerful elderly man sipping wine, showcasing hilariously bad art that’s actually brilliant.

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    #20

    Dispute Of St. Catherine With The Philosophers

    Old paintings featuring a strangely drawn dog with a human-like face, showcasing hilariously bad artistic style.

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    #21

    Just Get In The Pot, Brian

    Medieval old painting showing demons roasting a person in a pot over fire with a red background, hilariously bad art style.

    Apocalypse de S. Jean, en français. Gallica BnF.

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    #22

    Le Chat D'ostende

    Old painting of a cat knocking over sewing items on a red table, showcasing hilariously bad art with brilliant charm.

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    #23

    This Was Part Of A Manuscript Written By Jean Mansel In France 1454

    Medieval old painting depicting a comically rendered animal against an ornate floral background with bright colors.

    I wonder why cats always looked so weird in medieval drawings.

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    #24

    Medieval Partytime

    Medieval old painting depicting two figures in colorful robes with exaggerated poses and expressions.

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    #25

    Flower Piece With Cat And Mousetrap

    Split image showing a detailed old floral painting and a hilariously bad old painting of a cat with exaggerated expression.

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    #26

    He Is Handsome He Is Grace He Has A Little Bit Of That Monday Face

    Old painting featuring a humorous blue creature with human-like face and clawed feet in a medieval-style scene.

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    #27

    "For Small Creatures Such As We The Vastness Is Bearable Only Through Love"

    Medieval-style old painting of a monkey humorously holding a cat amid colorful floral decorations.

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    #28

    A Hound Riding On A Rabbit And A Rabbit Riding On A Snail Battle With Shields And Lances

    Medieval manuscript drawing of animals and a snail in a humorous scene from old paintings hilariously bad and brilliant.

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    #29

    This Isn't The Reincarnation I Requested

    Old painting of two children with exaggerated facial expressions and a small dog, showcasing hilariously bad art style.

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    #30

    What Is Making Him So Sad?

    Medieval-style painting of a cat playing a lute surrounded by flowers, illustrating hilariously bad old paintings.

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    #31

    Elephants From The Rochester Bestiary

    Medieval painting showing knights and animals with strangely distorted features in hilariously bad old paintings.

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    #32

    Salome Dancing

    Medieval-style old painting showing a person playing violin next to a contorted figure, highlighting hilariously bad old paintings.

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    #33

    The Dream Of The Three Wise Men

    Medieval old painting showing three men in bed with a winged angel above, an example of hilariously bad art.

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    #34

    Devil Bearing Jesus

    Medieval old painting showing a demon embracing a man in an orange robe, an example of hilariously bad but brilliant art.

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    #35

    Book Of Hours

    Medieval style old painting of an animal playing a violin surrounded by colorful abstract patterns and musical notes.

    The Morgan Library Museum Report

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    #36

    Fresco Cycle Featuring Scenes From The Life Of St. Martin Of Tours, Chapel In The Lower Church Of San Francesco In Assisi, Scene

    Old paintings featuring musicians in colorful medieval attire with quirky expressions and worn textures.

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    #37

    A Depiction Of A Leopard In The 12th-Century Aberdeen Bestiary

    Medieval painting of a bizarre red spotted animal with a curled tail, showcasing hilariously bad old paintings with unique charm.

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    #38

    Cat In His New Coat

    Medieval-style old painting of a mouse wearing a robe surrounded by colorful flowers and decorative elements.

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    #39

    Leo Flores

    Old painting of a knight on a horse with exaggerated features, showcasing hilariously bad but brilliant art style.

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    #40

    Quentin Matsys - A Grotesque Old Woman

    Old painting of a person with exaggerated facial features and traditional attire, showcasing hilariously bad art style.

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    #41

    Captivity Of Jeholachin King Of Israel

    Medieval old painting depicting knights and a group of men with oddly exaggerated expressions in a hilariously bad style.

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    #42

    Snail Attack

    Medieval old painting depicting knights and a figure attacking a large snail in a humorous and unusual scene.

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    #43

    Turns Out Elden Ring Is Historically Accurate!

    Medieval illustration depicting knights fighting giant snails, an example of old paintings that are hilariously bad yet brilliant.

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    #44

    John The Fearless

    Portrait of a man in old painting with red and black fur-trimmed clothing, showcasing hilariously bad old paintings with unique charm.

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    #45

    Combat Between Carnival And Lent

    Old painting showing a humorous medieval scene with characters on barrel carts, highlighting hilariously bad old paintings.

    Pieter Brueghel the Elder Report

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    #46

    Augustine Of Hippo

    Medieval old painting of a humorous creature with a distorted face and exaggerated features in colorful detail.

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    #47

    Egmont Breviary

    Medieval old painting of a monkey holding a blue orb surrounded by colorful floral and vine patterns, hilariously bad art style.

    The Morgan Library Museum Report

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    #48

    What?

    Medieval old painting featuring a crowned centaur and a queen in a humorous and awkward artistic style.

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    #49

    Book Of Hours

    Medieval old painting showing a man riding a large cat with a demon figure nearby, hilariously bad artwork.

    The Morgan Library Museum Report

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    #50

    The Feast Of The Bean King

    Old painting of a lively medieval feast with exaggerated expressions, showcasing hilariously bad art style and vibrant characters.

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