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.
- 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 HeelFace Turn thanks to Jonathan kicking his ass for wholesome, noble reasons, charming Speedwagon and turning him into a lifelong friend.
- Batman's foe 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.
- 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.
- 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 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.")
- A Clockwork Orange: Alex and his droogs wear bowlers.
- 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 Louis, who invented it. Its name is Doris.
- In The Hateful Eight Oswaldo Mobray sports one.
- James Bond
- Random Task, in Austin Powers: International Man of Mystery, a parody of Bond's Oddjob above, wears a bowler.
- Horvath, The Dragon from The Sorcerer's Apprentice.
- The bad guy newsies in Newsies wear bowlers.
- The Devil in The Imaginarium of Doctor Parnassus.
- One of character actor Terry-Thomas' trademarks in many of his films.
- Jim Carrey sported a green bowler with a question mark in several scenes as the Riddler in Batman Forever
- 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.
- Badger from Firefly. While not exactly "evil", he was an unsavory underworld character.
- Buffy the Vampire Slayer. The Monster of the Week in "Killed by Death". He even tips his hat to Buffy at one stage.
- 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".
- Bonanza: In "The Fighters," this was the signature headgear of the arrogant prize fighter that routinely goaded Hoss. Also worn by his handler.
- The Japanese heel manager Mr. Fuji was rarely seen without his iconic bowler hat in the WWF.
- 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.
- 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.
- Itchy, Clover, Sawbuck, Eggs, Biscuits, and Cans of mobster gang The Felt from Homestuck each wear one.
- 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.
- 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.
- Most of the members of Warren T. Rat's gang in An American Tail.
- Benito Mussolini, when not in his trademark fez.