History Main / DastardlyDapperDerby

* Jim Carrey sported a green bowler with a question mark in several scenes as the Riddler in ''Film/BatmanForever''.

* ''Series/BuffyTheVampireSlayer''. The MonsterOfTheWeek in "Killed by Death". He even tips his hat to Buffy at one stage.

* ''Series/{{Bonanza}}:'' In "The Fighters," this was the signature headgear of the arrogant prize fighter that routinely goaded Hoss. Also worn by his handler.

* 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.

* ''VideoGame/TeamFortress2'' has The Spy's [[http://wiki.teamfortress.com/wiki/Backbiter%27s_Billycock Backbiter's Billycock]]. Has a humorous variation in the [[https://wiki.teamfortress.com/wiki/Counterfeit_Billycock Counterfeit Billycock]]: a top hat supposedly disguised as a bowler hat.

[[folder:Web Comics]]

* In the WesternAnimation/BugsBunny short "WesternAnimation/AHareGrowsInManhattan", 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.

[[folder: Anime and Manga]]
* Speedwagon is introduced wearing one of these in ''Manga/JojosBizarreAdventurePhantomBlood''. This makes sense as Speedwagon is shown to be a rough and tumble street tough, so it makes sense he'd wear a fairly hard had to protect his head in a fight. [[WeaponizedHeadgear He's also put saw blades into the brim of his hat]], because this is Jojo. Becomes a DashinglyDapperDerby after his HeelFaceTurn thanks to [[DefeatMeansFriendship Jonathan kicking his ass for wholesome, noble reasons, charming Speedwagon and turning him into a lifelong friend]].
** The trope was brought back over thirty years later in ''Manga/JojosBizarreAdventureJojolion'', with the mysterious and extremely dangerous character Satoru Akefu, whose appearance is based on the Gentleman character from the paintings of Creator/ReneMagritte.
* ''Manga/MoriartyThePatriot'': Played with, since the first time VillainProtagonist William wears a bowler hat is actually ''after'' his reformation and beginning his RedemptionQuest.
[[/folder]]

* One ad for Advertising/HostessFruitPies has ComicBook/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 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.

* ComicBook/{{Casper}}'s cousin Spooky always wears one. He once claimed he got it from a babysitter who taught him how to scare and make mischief, though the ending of the story, which he was telling his "goil" Poil, seems to suggest he was [[UnreliableNarrator making it all up as he went along]]. Dapper as it may be, it can be a nuisance; he always has to remember to take it off to go through walls or when he turns invisible. ([[FunetikAksent "Sometimes dere are disadvantages to woikin' wit' props."]])

[[folder:Films -- Animation]]

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

[[folder:Films -- Live-Action]]
%%* ''Film/AClockworkOrange'': Alex and his droogs wear bowlers.
%%* In ''Film/TheHatefulEight'' Oswaldo Mobray sports one.
* ''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]].

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

* One of character actor Creator/TerryThomas' trademarks in many of his films.
* Jim Carrey sported a green bowler with a question mark in several scenes as the Riddler in ''Film/BatmanForever''
* In ''Film/TombstoneRashomon'', Johnny Behan, the cowardly and corrupt sheriff of Cochise County, in dressed in a natty suit and dapper brown derby, which the film crew gets him to keep on during his interview.

* One ad for Advertising/HostessFruitPies has Franchise/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]].

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

* ComicBook/{{Superman}} adversary Mister Mxyzptlk tends to wear one of these. Mxyzptlk is obsessed with making mischief to amuse himself, often at the expense of others.

* ''Film/AClockworkOrange'': Alex and his droogs wear bowlers.
* In ''Film/TheHatefulEight'' Oswaldo Mobray sports one.

Compare and contrast DashinglyDapperDerby.

[[Folder:Films -- Animation]]

[[folder:Film]]
* ''Film/AClockworkOrange'': Alex and his droogs wear bowlers.

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

Compare NiceHat, SharpDressedMan, BadassInANiceSuit, EvilBrit, DastardlyWhiplash.

* 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 Lewis, who invented it. Its name is [[FluffyTheTerrible Doris]].]]

* 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]].]]

[[quoteright:207:[[WesternAnimation/MeetTheRobinsons https://static.tvtropes.org/pmwiki/pub/images/bowlerhatguy_6.png]]]]
[[caption-width-right:207:Mustache twirling optional.]]

[[quoteright:200:[[WesternAnimation/MeetTheRobinsons https://static.tvtropes.org/pmwiki/pub/images/bowlerhatguy_2128.jpg]]]]
[[caption-width-right:200:Mustache twirling optional.]]

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

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.

* Nobody in England has worn a bowler hat since "Monty Python's Flying Circus" did the "Ministry of Silly Walks" sketch, since anyone foolhardy to venture out wearing one was liable to be accosted by an idiot who DEMANDED that he show the his "Silly Walk".

* In one of Creator/TexAvery's MGM shorts, ''WesternAnimation/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.

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

* In ''Disney/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]].]]

** 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'."

[[folder: Advertising]]

[[folder:Live Action TV]]

* One ad for DeliciousFruitPies has Franchise/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 one of Creator/TexAvery's MGM shorts,''WesternAnimation/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.