Hats as a clothing article are nowhere near as prominent as they used to be. Their unfamiliarity to the modern audience makes them a source of comedy. Particularly of the random variety. This trope comes in two forms: silly hats or inexplicable obsession with hats. See Also Nice Hat, where the hat is respected, and Hat Damage, which may result in hilarity. A cornerstone of the Brotherhood of Funny Hats.
- In Monty Python's The Meaning of Life, they 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.
- 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, only to find that there is always another (larger and fancier) hat underneath.
- Top Gear
- 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).
- 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. Watch it here.
- In "Biggles Dictates a Letter", he indicates to a Cloud Cuckoolander 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.
- Team Fortress 2: the 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 Team Fortress 2 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 Team Fortress 2 Pyromania update:
- 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.
- Every episode of Feed Dump ends with the following; "There may be better sources for news, but they don't have...*pulls out ridiculous piece of head-wear* this hat."
- The Simpsons episode "Marge Gets a Job" 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 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 who the hats belong to. 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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