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.

 

1. Al Pacino

The Godfather himself. In his most iconic role (in the most iconic Mafia movie), Michael Corleone was a war hero, a reluctant gangster who only got into the family business because his loved one were in need. But by the end of the second movie, the transformation was complete. Al went on to play plenty of other notable baddies in Scarface, Dick Tracy, Carlito’s Way, Donnie Brasco, and the notoriously bad Gigli.

 

2. James Gandolfini

When James Gandolfini walks into a restaurant, everyone in the joint sits up in their seats and acts on their best behavior. That’s because the guy is Tony Soprano, AKA not someone to be messed with. James has been on our gangster radar ever since True Romance, with similar roles in 8mm, Get Shorty, and The Mexican. Now he’s back playing a Mafia hitman alongside Brad Pitt in Killing Them Softly. And if you have to be typecast, it might as well be for one of the most acclaimed TV characters of all time.

 

3. Christopher Walken

Not always a gangster, but pretty much always at least a little creepy. Christopher Walken has played gangster types in Suicide Kings, True Romance, and the recent Seven Psychopaths, as well as other assorted black hats as a kidnapper in Nick Of Time, Catwoman’s crooked boss in Batman Returns, the evil angel Gabriel in The Prophecy, a Bond villain in A View To Kill, and the headless horseman of Sleepy Hollow. So he’s probably not the guy you want to be alone in a dark alley with.

 

4. Joe Pesci

The character actor is best known for his manic, loudmouth performances in mob movies, including Casino, Once Upon A Time in America, and GoodFellas, which won him an Oscar. In 2011, he sued producers of the movie Gotti for $3 million, after gaining 30 lbs. for the Mafioso title role that ultimately went to John Travolta. His most recent cinematic lawbreaker is the tax-evading owner of a brothel in Love Ranch.

 

5. Ray Liotta

Like many perpetual gangsters, Ray Liotta seems to always play one of two extremes ― cop or criminal. Of course, his criminal roles tend to be the most iconic, particularly his role as a cocaine-addicted mobster Henry Hill in the Mafia classic GoodFellas. He’s back at it this weekend in Killing Them Softly.

 

6. Michael Madsen

Justin Bieber wasn’t too bright when he decided to mess around with Michael Madsen’s daughter in his “As Long As You Love Me” video ― the guy has made it pretty clear that it’s not a good idea to cross him. He’s been a bad dude in Reservoir Dogs, Donnie Brasco, and Kill Bill, amongst others. But beating up the Biebs? Lock him away for life!

 

7. James Cagney

No list of gangsters would be complete without James Cagney. Back in the 30’s and 40’s, when gangster movies were even more popular than in recent decades, he defined the cinematic gangster tropes we’ve grown accustomed to today, with roles in classic films like White Heat, Angels With Dirty Faces, and The Public Enemy.

 

8. Samuel L. Jackson

A guy most famous for his use of the word “motherf-----” is bound to find himself playing a badass more often than not. He’s played such roles straight in movies like Pulp Fiction and Jackie Brown, and also makes fun of his tough guy image in stuff like Snakes on a Plane. Sam Jackson actually plays a good guy more often than you’d think, but you don’t want on his bad side regardless.

 

9. Robert De Niro

Yes, Robert De Niro, we’re talking to you. Though his recent roles have been more toned down and domestic, Robert De Niro became a legend through his mob-related roles in The Godfather Part II, Once Upon A Time In America, The Untouchables, Mean Streets, GoodFellas, Casino... and, well, this could go on awhile if we listed them all. He even parodied his gangster persona in Analyze This, as a mob boss in need of a shrink.

 

10. Jack Nicholson

Jack is known for all kinds of roles, from the deranged dad in The Shining to the OCD blowhard in As Good As It Gets. But three of his most memorable are gangsters, in Prizzi’s Honor, The Departed, and as The Joker in Tim Burton’s Batman (who was a gangster even before he fell into a vat of noxious chemicals and became a supervillain).

 

11. Warren Beatty

Warren hasn’t starred in a film in over a decade, but when he did, he played some of the most iconic gangsters to ever grace the screen. He was the male half of Bonnie and Clyde, the title role of Bugsy, and directed and starred as Dick Tracy, the detective who takes on organized crime.

 

12. Michelle Pfeiffer

Michelle has played her share of likable romantic leads, but she’s also proven she can hang with the bad boys. She played the widow of a Mafioso in Married To The Mob, a coke-addled mol in Scarface, and don’t forget her slinky criminal Catwoman in Batman Returns. She’s the proof that we need more tough females in the gangster genre!

 

13. Everyone Else On The Sopranos

James Gandolfini is far from the only perpetual gangster that starred on The Sopranos. After a six season run on HBO, virtually every Italian-American actor in the universe appeared on The Sopranos playing a Mafioso, and most of them can be seen in plenty of other mob-related entertainments, too. Since we can’t possibly list all of them, let’s just hope this covers everyone we missed.

Who is your favorite perpetual gangster?