History Main / TheHilarityOfHats

* ''WebVideo/EmpiresSMP'' Season 2: During the crossover event with the WebVideo/HermitcraftServer 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.

* ''LetsPlay/EmpiresSMP'' Season 2: During the crossover event with the LetsPlay/HermitcraftServer 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.

* When [=GoodTimesWithScar=] was first introduced in ''LetsPlay/PiratesSMP'', 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.

* Series/{{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 refinied style of dress.

* ''Series/TheGrandTour''
** 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.

* ''Fanfic/Plan7Of9FromOuterSpace''. Dr. Zarkendorf is introduced wearing SpaceClothes including a skullcap bearing a [[ZeeRust circular antennae for one of the new-fangled 'mobile telephones']].

-->'''Buster:''' {{Hold the front page}}. There are people on this planet dressed sillier than you, Proton.

* ''Radio/CabinPressure'': Martin has an apparently quite incredible [[CommissarCap captain's hat]], which looks even more ridiculous on him because he looks [[ExpectingSomeoneTaller so little like a captain]].

* ''WebVideo/FeedDump'': Every episode ends with the following; "There may be better sources for news, but they don't have...*''presenter pulls out ridiculous piece of head-wear''* '''this''' hat."
* A certain Daniel Swanson made a parody ConLang called "Kay(f)bop(t)", where each syllable has a letter in parentheses indicating what kind of ''hat'' the speaker has to wear while saying it: f is a fedora, t is a top hat, b is a baseball cap, and p is a pangolin-shaped hat. He says a speaker can wear a turkey-shaped hat if they lack a pangolin one, but such speakers are generally considered untrustworthy.

* ''Webcomic/GirlGenius'': The Jaegermonsters' obsession with hats is often PlayedForLaughs, though occasionally it is played for drama or plot advancement as well.

** While testing luxury cars in Albania Richard ponders whether the biometic sensors on his car can detect if he like certain cheeses or whether he's currently thinking about hats.

* A certain Daniel Swanson made a parody ConLang called "Kay(f)bop(t)", where each syllable has a letter in parentheses indicating what kind of ''hat'' the speaker has to wear while saying it: f is a fedora, t is a tophat, b is a baseball cap, and p is a pangolin-shaped hat. He says a speaker can wear a turkey-shaped hat if they lack a pangolin one, but such speakers are generally considered untrustworthy.
* In the 2022 ''WebAnimation/HomestarRunner'' Halloween Special, [[DumbMuscle Strong Mad's]] attempts to continue the scary story end up withb him giving all the characters hats, including a refrigerator and pile of hats.

** In another episode Homer suggests they add a scene in the ''Film/MrSmithGoesToWashington'' remake where the titular character, played by Mel Gibson, tries on lots of funny hats. [[NoJustNoReaction Mel quickly vetos it]].

[[quoteright:256:[[VideoGame/TeamFortress2 https://static.tvtropes.org/pmwiki/pub/images/gentlemanne_flip_crop_3615.png]]]]

[[folder:Film – Live-Action]]

[[folder: Newspaper Comics]]

* In ''WesternAnimation/TeenTitansGo'', 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 [[https://www.youtube.com/watch?v=vN5Tn6AV74Q model a series of silly hats]].

* ''Series/DoctorWho'': 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.

* ''Webcomic/Prolangs'' features a personification of Kay(f)bop(t) (see the Web Original folder below) who constantly switches between four hats.

* ''Creator/{{Bogleech}}'': One comic pokes fun at Creator/HPLovecraft's tendency to portray anything "alien" (i.e. [[ValuesDissonance "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 [[FauxHorrific wear hats on their stomachs instead of their heads]], which Lovecraft finds so [[AbsoluteXenophobe abnormal]] that it drives him insane.

* ''Webcomic/{{Bogleech}}'': One comic pokes fun at Creator/HPLovecraft's tendency to portray anything "alien" (i.e. [[ValuesDissonance "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 [[FauxHorrific wear hats on their stomachs instead of their heads]], which Lovecraft finds so [[AbsoluteXenophobe abnormal]] that it drives him insane.

* One ''Webcomic/AwkwardZombie'' strip parodying ''VideoGame/TeamFortress2'' by way of Creator/DavidAttenborough 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. [[spoiler: 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.
* One ''Webcomic/{{Bogleech}}'' comic pokes fun at [[Creator/HPLovecraft H. P. Lovecraft's]] tendency to portray anything "alien" (i.e. [[ValuesDissonance "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 [[FauxHorrific wear hats on their stomachs instead of their heads]], which Lovecraft finds so [[AbsoluteXenophobe abnormal]] that it drives him insane.
* In ''Webcomic/GirlGenius'', the Jaegermonsters' obsession with hats is often PlayedForLaughs, though occasionally it is played for drama or plot advancement as well.
* The various incarnations of Courtyard Droll from ''Webcomic/{{Homestuck}}'' have a fondness for hats: The bigger and more elaborate, the better. Jack Noir himself is saddled with a "ridiculous hat" during Act 6.
* In ''Webcomic/{{Galaxion}}'', Patty, TheMedic and a quirky, friendly soul, owns an insane hat collection.

* Every episode of ''WebVideo/FeedDump'' ends with the following; "There may be better sources for news, but they don't have...*''presenter pulls out ridiculous piece of head-wear''* '''this''' hat."

* There is one WesternAnimation/BugsBunny cartoon, "Bugs' Bonnets", where he 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.