History Main / DastardlyDapperDerby

* 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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* 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]]. [[=ArdRol=]]

* 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]].

* In the WesternAnimation/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.

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

* Franchise/{{Batman}}'s foe The Riddler dons one most of the time.

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.

* 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.

* In "Film/TheHatefulEight" Oswaldo Mobray sports one.

* {{Downplayed}} in the video for Music/PoetsOfTheFall's ObsessionSong "[[https://youtu.be/MKk1u5RMTn4?list=PLjACqN5i5sDWIIpg-5EB4WcitMMqnXhFP Carnival of Rust]]," where several of the vaguely menacing male [[CircusOfFear Carnival]] staff wear them, including SadClown Zoltar the fortuneteller, who manages to put off a customer by being so LoveHungry he becomes intimidating as a result.

* {{Downplayed}} in the video for Music/PoetsOfTheFall's ObsessionSong "[[https://www.youtube.com/watch?v=MKk1u5RMTn4 Carnival of Rust]]," where several of the vaguely menacing male [[CircusOfFear Carnival]] staff wear them, including SadClown Zoltar the fortuneteller, who manages to put off a customer by being so LoveHungry he becomes intimidating as a result.

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* In "Film/TheHateful8" Oswaldo Mobray sports one.

* Franchise/{{Batman}}'s foe ComicBook/TheRiddler dons one most of the time.

* The Fetchers in ''KeysToTheKingdom'' are dog-faced monsters who wear bowler hats.

* 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.

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

* 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]].]]

* BenitoMussolini, when not in his trademark fez.

* 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.) Refrained 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 refrained in the film.

** 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'.

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* 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.) Refrained 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 refrained in the film.