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.

It seems like Brad Pitt and Angelina Jolie have been engaged forever (its only been eight months), but as of right now there's still no definite plans for a wedding just yet.

During an interview with Extra, Brad admits that he and Angelina don't have a date set yet, but what about their old mantra that they wouldn't wed until same-sex marriage is legalized? Click after the jump to find out!

In the mind of a man, being named People magazine’s 'Sexiest Man Alive' is one of the highest honors. Well, at least I can imagine it is since I’m a woman, but the idea of having millions of women fawn all over you and being so good-looking that they slap your face on the cover of their annual issue is kind of a big deal.

Channing Tatum was named this year’s hottest guy (he can thank Magic Mike) but what about the past winners? You know, THE George Clooney, THE Brad Pitt? These men have stood the test of time and are still as hot and dreamy as ever. Some of the other past cover men we can’t say the same about. Remember Nick Nolte?

Here are our five past winners of People’s 'Sexiest Man Alive' title and they look just as good – or better – than they did in their prime.