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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.
- 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.
- 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.
- 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.
Groot: I am Groot.
Rocket: He's relieved you don't want him to wear it as a hat.
Groot: I am Groot.
Rocket: He hates hats.
Groot: I am Groot.
Rocket: On anyone, not just himself.
Groot: I am Groot.
Rocket: You see someone and think they have a weird head and then it just turns out part of their head is a hat. [beat] That's why you don't like hats?
- The picture book Go, Dog, Go! has a Running Gag involving a poodle appearing in increasingly ridiculous hats and asking another dog, "Do you like my hat?"
- The Dr. Seuss book The 500 Hats of Bartholomew Cubbins is about a boy who tries to take off his hat 500 times, but finds that there is always another hat underneath. The hats eventually start getting larger and fancier up until the eponymous 500th hat, which became so fanciful that the king had to have it for his very own...which, thankfully, ended the hat problem as there were no more hats after that.
- 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.
- Top Gear
- A series 15 episode opened with:
Jeremy: Tonight- Richard wears a blue hat!, James wears a different hat! And I wear a hat with things on it!
- 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.
Richard: You couldn't look more ridiculous if you tried.
(Jeremy turns his cap backwards)
Richard: Yep, you do. You've done the impossible.
- 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 biometic sensors on his car can detect if he like certain cheeses or whether he's currently thinking about hats.
- 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.
- Doctor Who: Fezzes are funny rather than cool, and the Doctor finding fezzes cool is funny to the other characters.
- 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.
- On Tic-Tac-Dough, Wink Martindale regularly modeled novelty hats sent in by viewers.
- 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...
- 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.
Martin: Look, I keep telling you, I didnít ask for extra. Itís just the standard amount of gold braid they put on a captainís hat these days.
Douglas: In the Democratic Republic of Congo, maybe...
- 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:
"That's a pretty catchy song," we said. "Who sings that?" Well, we don't want to upset you, so we won't type it here, but suffice it to say the band that wrote 'Safety Dance' has the most unthinkably offensive name we've ever heard.
- From the "Pyromania" update:
- 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.
- 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.
- One Bogleech 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.
- In Girl Genius, the Jaegermonsters' obsession with hats is often Played for Laughs, though occasionally it is played for drama or plot advancement as well.
- The various incarnations of Courtyard Droll from 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.
- One Awkward Zombie 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.
- Every episode of Feed Dump 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."
- 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.
- 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:
Meg: I want a new hat!
Chris: I want a new hat!
Stewie: I want them to have new hats!
- South Park: "Wall-Mart" changes into A Form You Are Comfortable With by putting on a hat. "Does this form please you?"
- 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.
- There is one Bugs Bunny 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.
- 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.
- 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.