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What's the first thing that comes to your mind when you hear the word jester?
It's the hat, isn't it?
Of course it is. That silly little hat with three cones made of cloth on top of it, bells at the end, and usually with two or three colors.
Much like kings, castles, and knights, the jester hat seems to be synonymous with medieval times. However, contrary to popular belief, authentic jesters did not always wear this particular hat. For example, Will Sommers, Henry VIII's jester, wore a more poofy hat, like berets on each-other, with a cloth flower on top.
So, why is this hat so famous?
Some of this may be attributed to Stańczyk, one of the more famous jesters- or at least in Poland. Even then, his iconic hat wasn't a full example, being plain red instead of multicolored.
The hat itself represents a donkey—traditionally, the hat is worn with one flap forward, and the other two off to the side, representing the nose and ears, respectively. So the hat in a sense, represented how the jester would make an ass out of himself.
Examples:
Anime & Manga
- Zazie Rainyday, from Mahou Sensei Negima!, though her hat is one color, two flaps, no bells. It still has the design, though.
- One of Sakura's costumes, though it's like the above example.
- Also, more than a few of the Clow Card spirits themselves wear hats like this.
Card Games
- Depending on the artist, this is what The Joker wears in a standard pack of cards.
Comic Books
- Of course, Harley Quinn's iconic red and black hat, though it has two flaps and no bells.
- Merryman, leader of the Inferior Five, had one of those, though it was monochrome.
- Minor Golden Age superhero the Jester (originally from Quality Comics, now owned by DC Comics) wore one (single coloured however).
- Daredevil foe the Jester (no relation to the abovementioned character) also wears one.
Film
- The Court Jester sports a variation of one, two flaps, checkered, and with bells. Of course, he spends just as much time with it on as he does with it off.
- Friar Carl wears one of these as part of his jester costume for the masquerade ball where he and the title character meet Dracula in the film Van Helsing. He twitches his head to make the bells ring in the graveyard where they stash the Frankenstein monster, out of anxiety, for laughs, or both.
- The imaginatively named Jester from the Puppet Master films wears this.
Folklore
- Till Eulenspiegel is a curious case. He originally didn't have one, going hatless or having a different jester hat. However, later adaptations and monuments have him wearing it.
Literature
- The Fool from Wyrd Sisters has one of these.
- Willard Phule, of Robert Aspirin's Phule's Company picks for his military pseudonyms names that play on his own last name, starting as Lieutenant Scaramouche (fool character from Italian commedia dell'arte) before getting promoted to Captain Jester. He becomes so popular with his new troops that they adopt an unofficial patch for their uniforms: a skull with a jester's cap.
- The cover art for Alan Gordon's Fools Guild Mysteries features figures wearing such a hat, and the main protagonists are a couple of professional jesters Theophilos (a.k.a. Feste from Shakespeare's Twelfth Night) and Claudia (a.k.a Viola from the same play). They are often depicted donning chalk makeup and costumes for performances.
- Edgar Allan Poe's short story "The Cask of Amontillado". During Carnival, Fortunato is wearing jester's motley, including a cap with bells. Poe repeatedly mentions the bells jingling throughout the story.
- In the same vein, his short story "Hop-Frog" features several jesters, all of whom "wore motley, with caps and bells".
Live-Action Television
- The jesters in the Centauri court from Babylon 5 have hats almost exactly like this, for some reason.
- Timothy Claypole wears a traditional one in the British television show Rentaghost
Music
- The album cover for Cowboy Mouth's 1996 album "Are You With Me" features a pan up shot of a Jester with an iconic 3 coned hat. Although the photo is black and white (grey tones), the hat appears to be a dark and light color variation.
- The Grateful Dead Songbook featured a skeleton wearing a droopy green jesters cap with bells, and holding a lute; the image went on to become one of their best-selling t-shirts, and spawned countless fan-art variations.
Newspaper Comics
Radio
Theater
- Oddly enough, Arlecchino, that is, the Harlequin from Commedia dell'Arte, occasionally subverts this trope in certain productions, wearing a hat more like Clopin's than the hat we all know and love.
- In some versions of Twelfth Night, Feste wears this.
- Touchstone from As You Like It wears this in some productions, and is believed by some to be the inspiration for the semi-famous reading jester
 ◊ picture.
Video Games
- The Monster Clown Dimentio from Super Paper Mario has a variation of this.
- On the subject of Monster Clowns, Shaco from the League of Legends series of video games wear this in all five of his skins.
- Cicero from The Elder Scrolls V Skyrim wears a variation of this, along with the rest of the outfit, after he kills a jester.
- Malcolm in the Legend of Kyrandia games wears one. In the third game, wearing a leather jerkin and/or a squirrel as a disguise will also remove the hat and cause fewer people to recognize him, despite no change in his loud yellow-and-purple sleeves and leggings. The jester hat seems to be the only thing most laypeople remember about him!
- Jester from Devil May Cry 3 unsurprisingly wears one of these as part of his outfit.
- Harle from Chrono Cross wears one of these along side a full jester ensemble.
Webcomics
- These frequently show up in Homestuck.
- Maytag wears a green cap in Flipside as part of her everyday outfit.
Western Animation
- Alias the Jester has a traditional hat.
- Bobby Hill sports one in "Joust Like a Woman", though it's hard to tell whether or not there are any bells..
- On The Simpsons when Homer talks a couple of late-middle-aged hippies into going on a "good old fashioned freak-out" he wears one of these while freaking the normals.
Have no fear, the Cosmic Fool is here, to blow the lid off your conformist button-down world!
- The aptly named Jester from Jane and the Dragon wears a variation of this, like the anime examples above.
- In Disney's The Hunchback of Notre Dame, the points of the King of Fools crown droop and have bells on the end like the flaps of a jester's cap.
- Bugs Bunny wears one, with two flaps that fit over his ears, in "Knighty Knight Bugs".
- In the "Steadfast Tin Soldier" segment from Fantasia 2000, the jack-in-the-box wears a harlequin hat to cover the fact that he's bald.
- Pinkie Pie has an interesting variation that she wears in the second half of the Season 3 premiere; five colors and two flaps. *
The hat is green, and the flaps are purple and blue for the right and orange and yellow for the left.
Real Life
- As it's been mentioned before, jesters commonly wore these, though they weren't always multicolored.
- The hat is almost as synonymous with Mardi Gras as it is with medieval times.
- The members of the Staten Island Quartett Club [sic] sported these, though they had four flaps.
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