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.