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

Nov. 28, 2012— -- 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."