Dastardly Dapper Derby

Mustache twirling optional.

A bowler hat is a rounded felt hat commonly worn from the 1850s to the early-to-mid-1900s, especially in Victorian Britain and The Wild West. 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? (Or Affably Evil, even Faux Affably Evil!) 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 Dashingly Dapper Derby, although they can overlap- see Wicked Cultured.

Compare Sharp-Dressed Man, Badass in a Nice Suit, Evil Brit, Dastardly Whiplash.

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Examples:

Advertising

• One ad for Hostess Fruit Pies has Spider-Man taking on a villain called Demolition Derby whose shtick (like Oddjob's) was that he wore a bowler hat he could throw as a weapon.

Anime & Manga

• Speedwagon is introduced wearing one of these in JoJo's Bizarre Adventure: Phantom Blood. 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. He's also put saw blades into the brim of his hat, because this is Jojo. Becomes a Dashingly Dapper Derby after his Heel–Face Turn thanks to 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 JoJo's Bizarre Adventure: JoJolion, with the mysterious and extremely dangerous character Satoru Akefu, whose appearance is based on the Gentleman character from the paintings of René Magritte.
• Moriarty the Patriot: Played with, since the first time Villain Protagonist William wears a bowler hat is actually after his reformation and beginning his Redemption Quest.

Comic Books

• Batman: The Riddler 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.
• Spooky the Tuff Little Ghost, Casper the Friendly Ghost's cousin, 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 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. ("Sometimes dere are disadvantages to woikin' wit' props.")
• Superman: Mister Mxyzptlk tends to wear one of these. Mxyzptlk is obsessed with making mischief to amuse himself, often at the expense of others.

Film — Animation

• Most of the members of Warren T. Rat's gang in An American Tail.
• In Meet the Robinsons, the "Bowler Hat Guy" appears to be the goofy Big Bad. Turns out the hat itself is an evil robotic mastermind intent on taking revenge on Lewis, who invented it. Its name is DOR-15, or Doris.

Film — Live-Action

• Random Task, in Austin Powers: International Man of Mystery, a parody of Bond's Oddjob above, wears a bowler.
• The Riddler sports a green bowler with a question mark in several scenes in Batman Forever.
• A Clockwork Orange: Alex DeLarge is the leader of a gang of "droogs"—Georgie, Dim and Pete—who get intoxicated on drug-laden "milk-plus" and engage in acts of of "ultra-violence" while dressed in all-white outfits accented with black bowler hats and canes .
• In The Hateful Eight, 'English' Pete Hicox, the outlaw masquerading as the hangman Oswaldo Mobray, sports one.
• The Devil in The Imaginarium of Doctor Parnassus.
• James Bond
  • The eponymous Big Bad of Goldfinger has his servant Oddjob with his blade-tipped bowler, which was made behind the scenes by turning a chakram into a hat.
  • Nick Nack in The Man with the Golden Gun wears more conventional bowler, albeit smaller.
• The bad guy newsies in Newsies wear bowlers.
• The Devil wears a bowler whenever he appears on Earth in Six Gun Savior.
• Horvath, The Dragon from The Sorcerer's Apprentice.
• In Tombstone Rashomon, 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.

Literature

• The Fetchers in Keys to the Kingdom 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 Punch-Clock Villain and The Pirates Who Don't Do Anything, but Mr Boggis of the Thieves' Guild is usually portrayed wearing a bowler hat. In Thud!, he refuses to replace it with a helmet when acting as a Special Constable.
  • In 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 the Verucca Gnome in 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 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.

Live-Action TV

• The idea of the Riddler wearing a green bowler hat and suit originated on the Batman (1966) TV series. the look was created by actor Frank Gorshin who dislike the green jumpsuit he originally had to wear.
• Bonanza: In "The Fighters," this was the signature headgear of the arrogant prize fighter that routinely goaded Hoss. Also worn by his handler.
• Buffy the Vampire Slayer. The Monster of the Week in "Killed by Death". He even tips his hat to Buffy at one stage.
• Badger from Firefly. While not exactly "evil", he was an unsavory underworld character.
• In Kamen Rider Gaim, Sid - a G-Rated Drug dealer, Hate Sink, and all-around slimeball - wears a black bowler.
• 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".

Music

• Downplayed in the video for Poets of the Fall's Obsession Song "Carnival of Rust," where several of the vaguely menacing male Carnival staff wear them, including Sad Clown Zoltar the fortuneteller, who manages to put off a customer by being so Love Hungry he becomes intimidating as a result.

Professional Wrestling

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

Theater

• Sally Bowles in 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.
• Mackie Messer in The Threepenny Opera 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.

Video Games

• The logo for Device6 has a prominent one.
• Overwatch: Ashe's robot butler/bodyguard B.O.B. wears one of these.
• Team Fortress 2 has The Spy's Backbiter's Billycock. Has a humorous variation in the Counterfeit Billycock: a top hat supposedly disguised as a bowler hat.

Web Animation

• As a crime lord that was inspired by Alex DeLarge from A Clockwork Orange, Roman Torchwick from RWBY wears red-banded black Derby hat. After his death, Neo takes to wearing it as a Tragic Keepsake.

Webcomics

• Itchy, Clover, Sawbuck, Eggs, Biscuits, and Cans of mobster gang The Felt from Homestuck each wear one.

Western Animation

• In one of Tex Avery's MGM shorts, Bad Luck Blackie, there is a black cat who caused bad luck to anyone whose path he crossed, wore a bowler. Averted however, as he seemed to only cause bad luck to those who deserved it.
• Looney Tunes:
  • In the Bugs Bunny 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 Looney Tunes 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.

Real Life

• Benito Mussolini, when not in his trademark fez.

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