The villains in the steampunk anime Steamboy wear bowler hats; as well as one of Batman’s best known villains, The Riddler.
In Stanley Kubrick’s film A Clockwork Orange the lead character Alex DeLarge wears a bowler hat
Stan Laurel and Oliver Hardy were well-known for their bowler hats, as was Lou Costello.
During the Silent Film Era, Charlie Chaplin’s character “The Tramp” almost always wore a bowler.
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