Brad Pitt is better-known for playing dashing hunks and dramatic leading men than he is for roles as a criminal, but he's showing off his darker side Killing Them Softly opens tomorrow. In the film, he plays a morally ambiguous “enforcer” with ties to the mob, and he looks pretty damn badass from what we’ve seen in the trailer.

It’s unlikely that this role will turn Brad into Hollywood’s go-to bad guy, but it got us thinking about all the other guys we always see popping up in these gangster flicks (a couple of them popping up with Brad in Killing Me Softly).

If we were casting a mob flick, these are the 13 wise guys (and girl) we'd want in it.