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The Hilarity of Hats

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Hats as a clothing article were once a sign of social standing but are nowhere near as prominent as they used to be. Their unfamiliarity to the modern audience makes them a source of comedy.
This trope comes in two forms: silly hats or inexplicable obsession with hats.
Compare Hat Damage, which may result in hilarity. A cornerstone of the Brotherhood of Funny Hats. A distinctive hat will often be a character's Signature Headgear. A parody of the Hat of Authority is a common way of puncturing the fragile dignity of said authority.
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In the short-lived BBC comedy Come Back Mrs. Noah, the crew have to dress up in spacesuits with helmets topped by a couple of plastic tubes, in which ping pong balls move up and down to show the wearer is breathing correctly. In another episode they have to wear Space Clothes with pointy radio beacon hats.
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Awkward Zombie: One strip parodying Team Fortress 2 by way of David Attenborough describes a Medic deciding which ally to Ubercharge as if it were a nature documentary, with the prospective "mates" displaying their hats to impress the Medic. The Medic picks a character with a whole stack of hats on his head... who turns out to be a disguised enemy Spy. In the rant, the artist admits that this is usually how she picks who to Ubercharge when playing as Medic.
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Plan 7 of 9 from Outer Space. Dr. Zarkendorf is introduced wearing Space Clothes including a skullcap bearing a circular antennae for one of the new-fangled 'mobile telephones'. Alien invader D'Ork singles him out from the other humans by referring to Zarkendorf as, "The one in the silly hat!"
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El Dorado has a Running Gag concerning the other character's opinions of Mississippi's choice of headwear:
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The "Marge Gets a Job" episode of The Simpsons has her suggesting "Funny Hat Day" with Tom Jones music playing regularly as a way of raising morale, after seeing a line of deeply disturbed employees (one popping back antidepressants, one a clear alcoholic, and the other brandishing a shotgun). A scene later the same employees look essentially the same, but they're wearing silly hats.
In another episode Homer suggests they add a scene in the Mr. Smith Goes to Washington remake where the titular character, played by Mel Gibson, tries on lots of funny hats. Mel quickly vetoes it.
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In The Parasol Protectorate, Alexia's best friend Ivy is renowned for having the worst taste in hats in the known world, with almost every character commenting on it. In Changeless, the switch to a secret door in a milliner's is hidden under a hat so deliberately hideous that no one would ever want to buy it. Ivy makes a beeline for it.
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The Grand Tour: While looking for an excuse for losing a race, Jeremey buys a massive fluffy hat and claims it was a purchase he thought long and hard about.
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Whose Line Is It Anyway? (all series) has a segment called "Dating Service", where the comedians pull different silly hats from a box and pretend they're making a video for a dating service.
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In Teen Titans Go!, Robin, Cyborg and Beast Boy ditch Starfire and Raven for what they claim to be a super cool "boys' night out." Turns out the boys' idea of a wild night is a visit to the hat shop, where they model a series of silly hats. In another episode, the Titans manage to capture a leprechaun and extort wishes from it. Their first two wishes are for cool hats on their heads and to rotate them 90 degrees.
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Galaxion: Patty, The Medic and a quirky, friendly soul, owns an insane hat collection.
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In the Skylanders games, you can give hats to your Skylanders (and in the fourth game, your captured villains), all of which provide varying stat bonuses. By the fourth game, there are hundreds to choose from.
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House of Mouse has used this several times. One was the Mad Hatter singing a song about hats ("Hats that are tall, and hats that are small, and hats that are totally off of the wall!"). Another was Goofy getting sidetracked in one of the trio's business cartoons by trying on hats in a hat shop.
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In Golf With Your Friends, cosmetic hats are awarded for playing the game for a while. They include many, many things that aren't strictly hats, such as a cake, a rotating radar dish, a hamburger, and a nest with eggs.
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On Tic-Tac-Dough, Wink Martindale regularly modeled novelty hats sent in by viewers.
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When GoodTimesWithScar was first introduced in Pirates SMP, he is wearing about four hats stacked on top of each other — a red top hat on top of a cyan top hat, on top of a bottle green tricorn hat, on top of a brown pirate's tricorn hat.
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In Discworld, overdressed characters are always described as wearing a hat with a feather in it. Vimes, who objects to even wearing a plumed helmet (he has a "plumes allowance" that he's never claimed), hates that the official ducal regalia includes one.
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Homestuck:
The various incarnations of Courtyard Droll have a fondness for hats: the bigger and more elaborate, the better. In most cases he ends up wearing towering, showy contraptions several times taller than he is. Jack Noir himself is saddled with a "ridiculous hat" during Act 6.
After John arrives in the Land of Wind and Shade and some of his house's objects end up scattered around, one of the local salamanders finds a crumpled top hat, decides that it's the most stylish thing he's ever seen, and starts a cultural craze around this item. Afterwards, the salamanders' growing obsession for "rumpled head objects", the ridiculous amounts of money they'll pay for them and the supposed shame they're bringing on their ancestors for their frivolity is a minor source of running jokes.
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In a hat gag that contemporary audiences would have got, Dracula in the titular novel turns up (off-camera, the event being related to van Helsing) to flee England wearing a straw hat. It doesn't suit him and to cap it all, it's October, after the season for wearing them ended.
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Guardians of the Galaxy Vol. 2: After several failed attempts to get Groot to bring him a prototype fin, Yondu gives Groot his Ravager badge and tells him to look for that symbol. Groot puts it on his head. Rocket explains that Groot thinks Yondu wants him to wear it as a hat, which Yondu denies.
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Feed Dump: Every episode ends with the following:
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Prolangs features a personification of Kay(f)bop(t) (see the Web Original folder below) who constantly switches between four hats.
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Our Miss Brooks: In "Bargain Hats For Mother's Day," Mrs. Davis asks Miss Brooks to sell the homemade hats she made. They feature an imitation sparrow perched upon imitation fruit. Mr. Conklin buys one for his wife Martha, Mr. Boynton buys one for his mother, Walter Denton gets one to use as a table centerpiece, while Genre Refugee Tex Barton buys one for his horse Lucy. Unfortunately, the recipients, even Lucy, are fanatics about having individualized wearing apparel...
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In another episode Homer suggests they add a scene in the Mr. Smith Goes to Washington remake where the titular character, played by Mel Gibson, tries on lots of funny hats. Mel quickly vetoes it.
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The Goodies. When Bill Oddie is inducted into the ancient Lancashire martial art known as "Ecky Thump", he's given the flat cap of a Novice. We're then shown the much bigger flat cap of a Master, and then the Grand Master is carried in wearing a flat cap so large it could be used as a sun umbrella.
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Hats are the main collectible of Struggling. Troy can wear two of them!
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The comedy I'm Gonna Git You Sucka has Mr. Big's Big Brim Club, where the title Big Bad's criminal minions relax and drink while wearing giant-sized hats.
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Girl Genius:
The Jaegermonsters' obsession with hats is often Played for Laughs, though occasionally it is played for drama or plot advancement as well.
Gil's hat, which the Jaegers gave as a sign of genuine respect. It's a ridiculous, hideous looking thing several times the size of Gil's head, yet conveys the inexplicable ability to convey to people who are otherwise unconvinced they are actually looking at Gilgamesh Wulfenbach.
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Bugs Bunny: In "Bugs' Bonnets", Bugs Bunny and Elmer Fudd keep having hats that fall from a delivery truck land on their heads, causing them to adopt the personas of the hats' owners. A judge's wig made Bugs act like he was running a trial, a grandma's hat made Elmer act like a little old lady, and a Boy Scout hat compelled Bugs to help Elmer cross the street.
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In StreetPass Mii Plaza, most of the hats that aren't Nintendo references fall under the silly hat category. Sometimes this is combined leading to things like your Mii wearing a replica of Princess Peach's castle.
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In Monty Python's The Meaning of Life, the Python troupe conclude that one of two concepts related to the eponymous question is that people are not wearing enough hats.
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Bogleech: One comic pokes fun at H. P. Lovecraft's tendency to portray anything "alien" (i.e. "different") as mind-bendingly horrific. In the comic, Lovecraft is introduced to a race of cute, utterly benign arthropod-like creatures with a fondness for hats, who attempt to converse politely with him: "Hello, friend soft-skin, do you like my hat?" The joke is that the aliens wear hats on their stomachs instead of their heads, which Lovecraft finds so abnormal that it drives him insane.
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In The Elder Scrolls III: Morrowind, the Colovian Fur Helm stands out as being very tall, pointy, and silly, essentially a bright yellow Santa Claus hat that stick straight up. As a sign, none of the characters who wear one can be taken seriously, for example Uncle Sweetshare, Tarhiel, and M'aiq the Liar.
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Little Britain: Somebody tries to win the world record for the tallest man by wearing an extremely tall top hat, until he learns that they're only measuring from the top of the head down.
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Fawlty Towers: In "The Builders", Basil prowls around looking for his cap, which is on his head. When he goes out, he puts another cap on top of it.
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SpongeBob SquarePants: Mr. Krabs sells SpongeBob a drinking hat he found in the garbage for $10, only to find afterwards that it is a hot collector's item as several collectors give him increasing offers for it up to $1,000,000. Then it turns out the hat is worthless, and SpongeBob got a clapping hat that's worth $1,000,000,000.
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Team Fortress 2 has so many wearable hats, and a player base so obsessed with said hats, that the game is occasionally known as "the world's number 1 war-themed hat simulator". To the point that any of the other examples on this list may be converted into a Team Fortress parody.
From the "Pyromania" update:
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A central motif in Super Mario Odyssey. Mario's regular hat gets shredded at the beginning during his attempt to save Peach from Bowser, so he allows Cappy, a member of a race of hatlike ghosts called Bonneters, to take its place. Cappy can transform into any of the various goofy-looking hats that Mario buys, and his eyes suddenly peaking out from time to time adds to the silly vibe. The various allies and enemies Mario encounters frequently wear silly hats themed after the areas they are found in, even characters like Goombas and Toads who don't usually wear hats. This is also a gameplay hint; those characters who aren't wearing hats can be Captured by Mario.
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Doctor Who:
Fezzes are funny rather than cool, and the Eleventh Doctor finding fezzes cool is funny to the other characters. He's also tried to add a Stetson, top hat and pirate tricorn to his ensemble with little success. If River Song is around she'll make her disapproval clear by shooting the hat.
The Thirteenth Doctor also has a love of funny hats, including a feathered helmet and, as a Call-Back to Eleven, another red fez.
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Monty Python's Flying Circus:
Near the end of the "Courtmartial" sketch, the British soldiers put on pixie hats (with fake pixie ears attached to them), to the audience's delight.
In "Biggles Dictates a Letter", Biggles indicates to a Cloudcuckoolander secretary whether or not he's dictating by wearing a hat with silly horns. His secretary still gets it wrong, writing it down when he isn't dictating and not writing it down when he is.
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In Duck Soup, there is a sketch where Harpo and Chico mess with a lemonade stand owner by knocking his hat off and then swapping it around with their hats when he tries to pick it up and put it back on.
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The Thirteenth Doctor also has a love of funny hats, including a feathered helmet and, as a Call-Back to Eleven, another red fez.
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Cabin Pressure:
Martin has an apparently quite incredible captain's hat, which looks even more ridiculous on him because he looks so little like a captain.
Arthur has his own hat, which he doesn't need to wear but made for himself. The hat goes undescribed, but given what Arthur's like, it almost certainly looks ridiculous.
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Top Gear
A series 15 episode opened with:
S16/E5 (The Snowmobile episode) reused this gag:
S18/E4 reused this gag again, but with a twist:
Once when Jeremy was reviewing an old Soviet-made car, the only good point he can find is there's enough headroom to drive in a hat. Cut to him in a wolfskin ushanka.
When in America, the presenters buy some hats so they'll blend in.
And in Romania, Jeremy buys a hat two sizes too small to blend in (while driving a supercar).
While testing luxury cars in Albania Richard ponders whether the biometric sensors on his car can detect if he like certain cheeses or whether he's currently thinking about hats.
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South Park: "Wall-Mart" changes into A Form You Are Comfortable With by putting on a hat. "Does this form please you?"
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In the 2022 Homestar Runner Halloween Special, Strong Mad's attempts to continue the scary story end up with him giving all the characters hats, including a refrigerator and pile of hats.
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Family Guy:
Peter Griffin thinks having his head smashed flat between two giant logs is more than worth a feather cap.
In a non-canon story where Peter finds a genie and gets Three Wishes:
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Empires SMP Season 2: During the crossover event with Hermitcraft on Season 9, the Hermits start a game of "Multi(verse) Tag" where a player must kill another player from the other server by a strange and difficult method chosen at random by a machine, and the Tagged player must wear a very large, off-kilter, pastel jester's hat to designate themself to be in the role.
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Frasier befriends a man named Bob who likes to wear gaudy tam o' shanters. When Bob offers one to him as a gesture of friendship, Frasier is horrified as it's completely out of place compared to his more refined style of dress.
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Friends
When the gang go on a beach trip in the third season finale, Rachel dons a giant sunhat that Chandler compares to a spaceship.
During a trip to London Joey buys a novelty top hat printed with the Union Jack from a gift stand. Chandler thinks it's stupid and refuses to be seen in public with Joey while he's wearing it.
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The following is a list of statements referring to the current page from other pages.

 The Hilarity of Hats
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Comedy Tropes
 The Hilarity of Hats
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Cranium Coverings
 Zoids: Wild / int_c3e5c40d
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