Dastardly Dapper Derby

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? 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.

Compare Nice Hat, Sharp Dressed Man, Badass in A Nice Suit, Evil Brit, Dastardly Whiplash.

Advertising

 * One ad for Delicious 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.

Comic Books

 * Batman's foe The Riddler dons one most of the time.

Film

 * 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
 * Goldfinger has Oddjob with his blade-tipped bowler.
 * Nick Nack in The Man With the Golden Gun wears more conventional bowler, albeit smaller.
 * Horvath, The Dragon from The Sorcerers Apprentice.
 * The bad guy newsies in Newsies wear bowlers.
 * The Devil in The Imaginarium of Doctor Parnassus.

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.

Live Action TV

 * 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.

Professional Wrestling

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

Video Games

 * Team Fortress 2 has The Spy's Backbiter's Billycock.

Western Animation

 * 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.
 * 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. Though his evilness could be debated, 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.

Real Life

 * Benito Mussolini