Brad Pitt, James Gandolfini on 'Killing Them Softly' and Saucy Chanel Ad

James Gandolifini Talk Dark Moments in Killing Them
WATCH Brad Pitt on 'Killing Them Softly,' Chanel Ad

Brad Pitt stole the hearts of millions of women more than 20 years ago when he played a cowboy hitchhiker in "Thelma and Louse," and cemented himself as a bonafide tough guy in films like "Fight Club" and "Inglorious Bastards."

His range is wide, from "Benjamin Button" to his Oscar-nominated role last year in "Moneyball," and now the 48-year-old is taking on the mob.

In an interview with "Nightline" anchor Cynthia McFadden, Pitt and co-star James Gandolfini talked about starring in the new film, "Killing Them Softly," which is out in theaters on Friday. Both actors play hit men, two old friends hired to chase down a group of wannabe criminals who decide to knock over a mob-protected card game.

It's a return to a tough-guy role for Pitt after recently giving us a glimpse of his softer side as the super-serious Chanel No. 5 perfume pitchman.

"I kind of liked it," Pitt said of the ad, which has gone through a series of YouTube parodies and was recently made fun of on "Saturday Night Live."

"I stay blissfully naïve to the chatter out there in the world," he said. "But fair play."

For Pitt, "Killing Them Softly" was a quick sell. He said it took him all of 30 minutes to decide to do the film and he was eager to work with director Andrew Dominik again.

Dominik directed him in the 2007 film, "The Assassination of Jesse James by the Coward Robert Ford." The movie was a box office disaster and Pitt said Dominik had trouble finding another project afterwards.

"He was in, like, director's jail, because 'Jesse James' wasn't considered a success," Pitt said. "To me, it's the one I am most proud of."

So when Dominik called and told Pitt he was excited about a new story, Pitt readily agreed. But Gandolfini was a tougher sell. Having been the man who made Tony Soprano a household name, the 51-year-old Emmy winner said he didn't want to take on "another mob guy" role.

"I have done it for 10 years," Gandolfini said. "I had no more tricks. I couldn't pull anything out of the hat for this kind of thing."

But when Dominik persisted, Gandolfini said he gave in for one last stand as the "mob guy."

"He tortured me, tortured me, tortured me," Gandolfini said. "Then I started thinking, 'I've done a bunch of these guys and this is kind of the final nail in the coffin. This is where you are at the end.' So maybe if I played it that way in my mind, this is the last one, then it got interesting."

Not only that, but Gandolfini had worked with Pitt before on another crime thriller: Quentin Tarantino's 1993 film, "True Romance."

"That was my first big movie, I think," Gandolfini said.

"He was the tough guy coming in the door and I was the stoned guy on the couch," Pitt said.  

The plot for "Killing Them Softly" is based on a 1970s crime novel, but the story unfolds in the context of the 2008 financial crisis.

"I've always been of the opinion that many crime movies are about capitalism," Dominik said. "It's the genre where everyone is chasing a buck, and it's generally about the idea of getting rich quick. I just saw the parallels between that and what was going on with the bailout at the time and it just seemed too good to ignore."

What Angelina Jolie Thinks of 'Killing Them Softly'

The film suggests that the people running the mob and the people running the economy have a lot in common. George W. Bush and Barack Obama are all in the cross hairs, and not even Thomas Jefferson escapes unscathed.

"The movie is almost like a political cartoon," Dominik said. "It does exaggerate certain things for effect, but it's certainly one way to look at America."

Politics aside, those hoping for good, old-fashioned mob movie violence will not be disappointed, and that's where actor Ray Liotta of "Goodfellas" fame comes in. Only this time, Liotta's character, Markie Trattman, is on the receiving end.

"It was a whole different thing to take the beating, and really hard," Liotta said. "And I wanted to do it all myself I didn't want a stunt guy to do it because I thought it was important to show real fear."

Dominik said he wasn't sure about casting Liotta in the role at first because didn't know how the actor would feel about being the punching bag.

"Any scene involving violence at all hinges on the performance of the victim," Dominik added. "And I was just really impressed."

There is no question that "Killing Them Softly" is a hyper-masculine film. There is only one woman in the entire cast and she appears briefly as a prostitute.

"I think any movie that deals with violence in some way is also dealing with masculinity," Dominik said. "If I could've done a completely without women, I would have."

As for women watching the film, one can't help but wonder what Angelina Jolie, the mother of her and Pitt's six children, thought of it.

"She actually likes the film," Pitt said. "She's a tough audience and she like this one a lot. I didn't really ask her why, I just took that and--"

"And ran," Gandolfini chimed in, laughing.