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- Lucky the Leprechaun, the mascot for General Mills' Lucky Charms cereal, wears a green bowler with a shamrock stuck in it. While not evil, he is a trickster.
- The British bank Bradford & Bingley portrayed its two namesakes as bowler-hatted city gents. Eventually, its logo became a stylised version of the hat itself.
- Likewise there was a period when the symbol of the UK Inland Revenue was a stereotyped taxman in pinstripe suit and bowler.
- Golden Age Green Lantern sidekick Doiby Dickles is named after his hat.
- Richie Rich's butler, Cadbury, almost always wore a bowler hat in public.
- Bumbling look-a-like detectives Thompson and Thomson in Tintin.
- Timothy Aloysius Cadwallader "Dum Dum" Dugan of the Howling Commandos and S.H.I.E.L.D. wears his corporal's stripes on the front of his signature bowler hat.
- Seamus McFly in Back to the Future Part III.
- Curly of The Three Stooges always looked dapper in his "doiby".
- Lou Costello of Abbott and Costello often wore one of these.
- In The Apartment, CC Baxter buys himself a bowler after he gets his second promotion.
- Detective Sergeant Mendel (Harry Andrews) in "The Deadly Affair"(based on John Le Carre's "Call For The Dead")
- Sherlock Holmes's friend and biographer Dr. Watson is often portrayed with a bowler hat, as the Quintessential British Gentleman.
- Cornelius Fudge, Minister of Magic from Harry Potter, was often described as having a lime green bowler.
- Sweyn embarrasses his brothers in The Great Brain Does It Again when he returns from high school back east wearing a derby hat along with a fancier, more grown-up, style suit than a boy his age would wear in Adenville.
- The Night Circus: Any time Marco ventures outside, he is wearing a dashing bowler from a line of seemingly identical hats that were in his flat when he moved in. Isobel looks for a bowler whenever she is expecting him.
Live Action TV
- Mr. Steed of The Avengers is likely the Trope Codifier.
- Lord Bowler (so named for his hat) in The Adventures of Brisco County, Jr. was the Anti-Hero to Brisco's hero.
- The Czechoslovakian character Pan Tau usually wore a magic Bowler Hat.
- In the TV adaptation of Jeeves and Wooster, Jeeves' hat of choice is bowler hat.
- Monty Python's Flying Circus often used these as indicative of bankers and accountants.
- Probably the principal factor in the demise of the bowler hat was "Monty Python's Flying Circus"'s infamous sketch, "The Ministry Of Silly Walks", which commenced with John Cleese, in full Civil Service getup, including bowler hat, walking down Whitehall toward his office, doing an impression of a spider on a hotplate; for ever afterward, anyone foolhardy enough to venture out of doors wearing a bowler risked being accosted by idiots demanding that they do a Silly Walk.
- Snoopy of Peanuts wears one of these when he's donning his "World Famous Attorney" persona.
- Worn by nearly all the men in The Champion Pub.
- The protagonists of The Men from the Ministry wear nice, black bowler hats, as do all civil servants in the show.
- Henry Hatsworth, the current image source for the Quintessential British Gentlemen page.
- Accessible as headgear in SSX 3.
- The robot butler/companion Codsworth in Fallout 4 can't (or won't) wear any equipment in the game except for one of these.
- As a robot originally designed to be a gentleman butler for the affluent, Marquis from Battleborn wears a dandy looking derby as part of his ensemble.
- Baron von Fogel of The League of S.T.E.A.M. wears one.
- Homsar from Homestar Runner wears one, but he is more demented than dashing. Whenever he speaks, his bowler hat will actually fly off his head for a while until he stops talking.
- Sir Winston Churchill
- Charlie Chaplin
- Stan Laurel and Oliver Hardy
- Styme of The Little Rascals got his trademark derby from Stan himself, who had taken a liking to him.
- Probably the best place to see large numbers of men wearing Bowler Hats is Belfast or Londonderry on the 12th of August every year: the date is the anniversary of the Battle of the Boyne in 1690; when the deposed King James II attempted to capture Londonderry, the apprentice boys shut the city gates and kept him out; now , every year, the Orange Order (an organisation analagous to the Freemasons in the rest of Britain) holds a mass procession through the city wearing full regalia of grey suit, white gloves, purple sash, and all topped off with a resplendent Bowler Hat, accompanied with flute bands and led by a massive "Lambeg" drum.