[[quoteright:200:[[MeetTheRobinsons http://static.tvtropes.org/pmwiki/pub/images/bowlerhatguy_2128.jpg]]]]

A bowler hat is a rounded felt hat commonly worn from the 1850s to the [[TheRoaringTwenties early]]-to-[[TheFifties mid-1900s]], especially in VictorianBritain and TheWildWest. Bowler hats were once considered the national hat of England, and used to be associated with the upper-middle class there, especially with bankers, in the early half of the 20th century.

Nobody is sure why bowler hats can be associated with evil characters, since most of the time they show a character who is civilized. {{Irony}}, perhaps? Some creators might also be aware that a bowler is actually a fairly functional helmet (it was originally designed to protect gamekeepers on horseback from low branches), so a character wearing one may be anticipating getting into a fight.

Compare and contrast DashinglyDapperDerby.

Compare NiceHat, SharpDressedMan, BadassInANiceSuit, EvilBrit, DastardlyWhiplash.
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!!Examples:

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[[folder: Advertising ]]

* One ad for DeliciousFruitPies has SpiderMan taking on a villain called Demolition Derby whose shtick (like Oddjob's) was that he wore a [[WeaponizedHeadGear bowler hat he could throw as a weapon]].

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[[folder: Comic Books ]]

* Franchise/{{Batman}}'s foe ComicBook/TheRiddler dons one most of the time.
* In ''The Haunted World of El Superbeasto'', presented by Rob Zombie, sub-story ''Suzie-X'', the characters Bobbie Wulfgang and the Moloko Boys are werewolves who speak, dress, and act as an homage to Alex and his droogs from ''A Clockwork Orange.'' Only three of them wear bowlers.

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[[folder: Film ]]

* ''Film/AClockworkOrange'': Alex and his droogs wear bowlers.
* In ''WesternAnimation/MeetTheRobinsons'', the "Bowler Hat Guy" appears to be the [[IneffectualSympatheticVillain goofy]] BigBad. Turns out [[spoiler:''the hat itself'' is an evil robotic mastermind intent on taking revenge on Louis, who invented it. Its name is [[FluffyTheTerrible Doris]].]]
* ''Film/JamesBond''
** The eponymous BigBad of ''Film/{{Goldfinger}}'' has [[TheDragon his servant]] Oddjob with his blade-tipped bowler, which was made behind the scenes by turning a [[RingsOfDeath chakram]] into a hat.
** Nick Nack in ''Film/TheManWithTheGoldenGun'' wears more conventional bowler, [[DepravedDwarf albeit smaller]].
* Random Task, in ''Film/AustinPowersInternationalManOfMystery'', a parody of Bond's Oddjob above, wears a bowler.
* Horvath, TheDragon from ''Film/TheSorcerersApprentice''.
* The bad guy newsies in ''Film/{{Newsies}}'' wear bowlers.
* The Devil in ''Film/TheImaginariumOfDoctorParnassus''.
* One of character actor Creator/TerryThomas' trademarks in many of his films.

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[[folder: Literature ]]

* The Fetchers in ''KeysToTheKingdom'' are dog-faced monsters who wear bowler hats.
* The bledlows [Unseen University porters] in ''Literature/{{Discworld}}'' are generally petty bullies who victimise the students and have secret contempt for the wizards. They are described as not just wearing bowler hats, but having heads ''designed'' to wear bowler hats.
** Not exactly dastardly, existing in the overlap between PunchClockVillain and ThePiratesWhoDontDoAnything, but Mr Boggis of the Thieves' Guild is usually portrayed wearing a bowler hat. In ''Discworld/{{Thud}}'', he refuses to replace it with a helmet when acting as a Special Constable.
** In ''Discworld/{{Snuff}}'', the groundskeepers on the Ramkin estate wear leather bowlers as a form of protection and signification of their profession. They're not villainous, but pretty rough characters.
** Less "evil" and more "annoying and unpleasant", but [[spoiler:the Verucca Gnome]] in ''Discworld/{{Hogfather}}'' is described as wearing "the type of hat known in various parts of the multiverse as 'bowler', 'derby' or 'the one that makes you look a bit of a tit'."
* Like his movie counterpart, Oddjob in ''Literature/{{Goldfinger}}'' wears one with a leadlined brim, making it a lethal throwing weapon. Using it for that purpose however damages the felt around it, forcing him to always repair it afterwards.

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[[folder: Live Action TV ]]

* Badger from ''Series/{{Firefly}}''. While not exactly "evil", he was an unsavory underworld character.
* ''Series/BuffyTheVampireSlayer''. The MonsterOfTheWeek in "Killed by Death". He even tips his hat to Buffy at one stage.

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[[folder: Professional Wrestling ]]

* The Japanese heel manager Wrestling/MrFuji was rarely seen without his iconic bowler hat in the WWF.

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[[folder: Theater ]]

* Mackie Messer in ''Theatre/TheThreepennyOpera'' by Bertolt Brecht and Kurt Weill; AKA Mack the Knife. May be the origin of this trope, and inspiration for ''A Clockwork Orange'''s Alex and his droogs, as Alex also carried a sword cane (really more of a knife cane.) Retained in the film starring Raul Julia, although his character also wears a seal fur top hat in some scenes.
* Sally Bowles in ''Theatre/{{Cabaret}}'' by Christopher Isherwood. While Sally is not sinister, she lives in sinister times, is given to inebriated debauchery, seduces men for favors, has no moral compass, and she most admires her friend Elsie, who died young "from too much pills and liquor, but when I saw her laid out like a queen, she was the happiest corpse I'd ever seen." And "When I go, I'm going like Elsie." Suicidal Weltschmerz indeed. Also retained in the film.

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[[folder: Video Games ]]

* ''VideoGame/TeamFortress2'' has The Spy's [[http://wiki.teamfortress.com/wiki/Backbiter%27s_Billycock Backbiter's Billycock]].
* The logo for ''VideoGame/{{Device6}}'' has a prominent one.

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[[folder: Web Comics ]]

* Itchy, Clover, Sawbuck, Eggs, Biscuits, and Cans of mobster gang The Felt from ''Webcomic/{{Homestuck}}'' each wear one.

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[[folder: Western Animation ]]

* In the BugsBunny short "A Hare Grows in Manhattan", the leader of the gang of dogs is a bulldog wearing a bowler hat. There was another bullying bulldog in WesternAnimation/LooneyTunes cartoons named Spike, who also wore a bowler, who was teamed with Chester the Terrier.
* Another Bugs Bunny short "Bowery Bugs" features Steve Brodie, after the historic Brooklyn Bridge daredevil jumper, as a derby wearing thug who is always looking for an easy score between bouts of fearful superstition.
* In one of Creator/TexAvery's MGM shorts,''BadLuckBlackie'', there is a black cat who caused bad luck to anyone whose path he crossed, wore a bowler. Though his evilness could be debated, as he seemed to only cause bad luck to those who deserved it.
* Most of the members of Warren T. Rat's gang in ''WesternAnimation/AnAmericanTail''.

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[[folder: Real Life ]]

* UsefulNotes/BenitoMussolini, when not in his trademark fez.
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