Vanilla ice in Cool as Ice…Am I suppose to like this guy? He seems like a complete jerk. Sly Stallone in Cobra is hilariously over the top trying to be cool. Joe Piscopo in Dead Heat. Diceman in The adventures of Ford fairlane. Love some Chuck Norris/ Steven Segal movies but they often make the characters less cool. Hallie Berry in a lot of movies: X-men as Storm (who is a f.ing goddess and awesome character!) Catwoman, John wick 3, die another day, etc. George Clooney in From Dusk till dawn. Cage in Drive Angry. Too many Video game / comic book movies to mention.