Bad Boys of Cinema

I have to make an infographic on the transformation of the "bad boy" in american cinema.
Im currently in the process of researching different bad boys in cinema and im struggling a bit

so far i have

Jim Stark -50's
John Bender -80's

Edward Cullen(unfortunately) - Present

Im trying to use real iconic ones

anyone know of any good ones from the 30's and 40's and other eras
 
Tony Stark from Iron Man... he's a bad-ass.

Edward Cullen ... I would argue... is not a bad-boy...

What about... Malfoy from Harry Potter.. haha
 
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Christian Slater - Heathers
Mickey Rourke - just about anything, but how about 9 1/2 Weeks
Keifer Sutherland - Stand By Me
 
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