History Main / DastardlyDapperDerby

* In ''The Haunted World of El Superbeasto'', presented by Rob Zombie, sub-story ''Suzie-X'', the characters Bobbie Wulfgang and the Moloko Boys speak, dress, and act as an homage to Alex and his droogs from ''A Clockwork Orange.'' Only three of them wear bowlers.

* 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.

* Sally Bowles in ''Theatre/Cabaret'' by Christopher Isherwood. While Sally is not sinister, she lives in sinister times, is given to inebriated debauchery, 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 you'd ever seen." And "When I go, I'm going like Elsie." Suicidal Weltschmerz indeed. Also refrained in the film.

* Mackie Messer in ''The Threepenny Opera'' by 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.

* Like his movie counterpart, Oddjob in ''Literature/{{Goldfinger}}'' wears one with a leadlined prim, making it a lethal throwing weapon. Using it for that purpose however damages the felt around it, forcing him to always repair it afterwards.

* In ''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]].]]

** The eponymous BigBad of ''Film/{{Goldfinger}}'' has Oddjob with his blade-tipped bowler, which was made by turning [[RingsOfDeath chakram]] into a hat.
** Nick Nack in ''Film/TheManWithTheGoldenGun'' wears more conventional bowler, albeit smaller.

* Like his movie counterpart, Oddjob in ''Literature/{{Goldfinger}} wears one with a leadlined prim, making it a lethal throwing weapon. Using it for that purpose however damages the felt around it, forcing him to always repair it afterwards.

* ''Film/{{Goldfinger}}'' has Oddjob with his blade-tipped bowler.

* The bad guy newsies in ''{{Newsies}}'' wear bowlers.

* In one of 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.

* The Japanese heel manager Mr. Fuji was rarely seen without his iconic bowler hat in the WWF.

* BenitoMussolini

* The Devil in ''TheImaginariumOfDoctorParnassus''.

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

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

* Most of the members of Warren T. Rat's gang in ''AnAmericanTail''.

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

[[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.

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

[[AC: ComicBooks]]
* {{Batman}}'s foe TheRiddler dons one most of the time.

[[AC:{{Film}}]]
* ''Film/AClockworkOrange'': Alex and his droogs wear bowlers.
* In ''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/{{Goldfinger}}'' has Oddjob with his blade-tipped bowler.

* Horvath, TheDragon from ''Film/TheSorcerersApprentice''.
* The bad guy newsies in ''{{Newsies}}'' wear bowlers.

[[AC:{{Literature}}]]
* The Fetchers in ''KeysToTheKingdom'' are dog-faced monsters who wear bowler hats.
* The bledlows [Unseen University porters] in ''{{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.

[[AC:LiveActionTV]]
* Badger from ''{{Firefly}}''. While not exactly "evil", he was an unsavory underworld character.

[[AC:VideoGames]]
* ''VideoGame/TeamFortress2'' has The Spy's [[http://wiki.teamfortress.com/wiki/Backbiter%27s_Billycock Backbiter's Billycock]].

[[AC:WesternAnimation]]
* 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 LooneyTunes cartoons named Spike, who also wore a bowler, who was teamed with Chester the Terrier.

[[AC:RealLife]]
* BenitoMussolini

* ''{{Goldfinger}}'' has Oddjob with his blade-tipped bowler.
** Nick Nack in ''TheManWithTheGoldenGun'' wears more conventional bowler, albeit smaller.
* Horvath, TheDragon from ''TheSorcerersApprentice''.

* ''TeamFortress2'' has The Spy's [[http://wiki.teamfortress.com/wiki/Backbiter%27s_Billycock Backbiter's Billycock]].

* ''AClockworkOrange'': Alex and his droogs wear bowlers.