For every person who hides insecurity and inferiority behind a mask of cool, Patrick Bateman is your patron saint. Christian Bale’s amazing performance as the hollow serial killer dressed in the height of 1980s fashion turns AMERICAN PSYCHO from slasher into satire of what made that decade the years of total excess. Bale is awesome and somehow turns Phil Collins and Huey Lewis into soundtracks with a much different audience than originally envisioned. Bateman is cool, crazy and the definition of what deserves the top spot on this list.
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George Clooney is already a cool guy and has played multiple cool criminals in FROM DUSK TIL DAWN and O BROTHER WHERE ART THOU?, but it is his performance as Danny Ocean that earns him this spot. Steven Soderbergh’s remake of the Rat Pack heist flick resulted in two enjoyable sequels, each of which is anchored by Clooney’s super smooth mastermind who can pull of the most convoluted robberies without breaking a sweat.
Another character portrayed in very different ways by multiple actors, The Joker remains one of the coolest bad guys thanks to his complete disassociation with reality while still maintaining a flair for the dramatic. Plus, no one can pull of purple quite the same was as Mr. J. Whether it be his gangster appearance in SUICIDE SQUAD, his animated frenemy mode in THE LEGO BATMAN MOVIE or the classic portrayals by Heath Ledger and Jack Nicholson, The Joker is one of the coolest criminals ever.
Portrayed by three actors, Hannibal Lecter is one of the greatest villains in film history. While Mads Mikkelsen may have given him the most style, there is no doubt that Anthony Hopkins award-winning portrayal is the one audiences will most remember as the cannibalistic embodiment of true cinematic evil.
BONNIE & CLYDE is one of the greatest Hollywood films of all time but it is not just the story that makes it legendary. Both Faye Dunaway and Warren Beatty are sexy as hell in this crime caper that turned the outlaws into big screen idols. Beatty may have trouble getting it up and sometimes makes the wrong decisions, but his passion and fashion sense exude cool.
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Quentin Tarantino has made a career out of criminals who are cooler than cool. While I was tempted to put Jules and Vincent Vega on this list, Michael Madsen’s even-tempered and sadistic Mr. Blonde won out. RESERVOIR DOGS may be Quentin Tarantino’s masterpiece but it would not have been such a classic if not for Mr. Blonde’s dance moves and skills with a blade.
One of the most haunting serial killers in film history, Kevin Spacey’s John Doe is a master of planning and execution, literally. While he may not be the most fashionable guy on this list, his panache and thematic slayings make him one of the most unique. With so little screen time, John Doe still manages to pervade every second and every frame of SEVEN.
Michael Caine is just awesome. While he has played all sorts of criminals and good guys in his life, his role as the tough Jack Carter in GET CARTER is one of the most underseen gems on this list. Caine is at his best as a youthful gangster out for blood. Forget the lackluster remake and check out the original!
Daniel Day-Lewis may have just retired from acting but his career speaks for itself. While GANGS OF NEW YORK may have been one of his pulpier and more mainstream roles, his performance as Bill the Butcher is nonetheless eternally watchable. The Butcher is the type of character that we haven’t seen since the golden days of Hollywood. He is a classic bad guy but one who also serves as something of an anti-hero.
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NATURAL BORN KILLERS is all about the glorification of criminals in the early 1990s when true crime was all the rage. Well, fast forward a couple of decades and you are hard pressed to find a killer as charismatic as Woody Harrelson as Mickey Knox. Paired with Juliette Lewis, Harrelson’s Mickey is a good ol’ boy with an evil mind and the ability to kill without remorse. He is a terrifying character but one you could also see yourself throwing back some brews with.