'KILLING THEM SOFTLY': James Gandolfini plays a stone-cold killer. The Weinstein Company

When director Andrew Dominik asked James Gandolfini if he'd be interested in playing a boozing, whoring Mafia hit man in his new film, "Killing Them Softly," the actor said no, thanks.

The character of Mickey "had some overtones, similarities to people I've played in the past," says Mr. Gandolfini, referring to Tony Soprano, the New Jersey mob boss he portrayed for six seasons in the HBO series "The Sopranos."


Based on the 1974 novel "Cogan's Trade," by George V. Higgins, the film stars Brad Pitt as Jackie Cogan, a mobster called upon to investigate a robbery at an illegal card game run by an amiable thug named Markie ( Ray Liotta ). After discovering who committed the crime—a pair of lowlifes played by Scoot McNairy and Ben Mendelsohn —Cogan ropes in Mickey but soon realizes he's not quite up for the job.

The theme of the film, says Mr. Pitt in an interview, is that everybody's on his own: "These are the rules, and if you don't play by the rules you get crushed," he says.

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Brad Pitt Kills Them Softly

Mr. Pitt, who also produced the film, collaborated with Mr. Dominik on 2007's "The Assassination of Jesse James by the Coward Robert Ford," a commercial flop that brought in less than $4 million domestically, despite positive reviews. "I always felt that ['Jesse'] was a fine-wine kind of film, and it would find its time and place as it aged," says Mr. Pitt, adding that the economic themes in the new film, set during the 2008 banking crisis, "are as applicable as ever."

In addition to lurid violence and grotesque profanity—including a discussion between two criminals about the merits of bestiality—the film contains a lot of background speechifying by George W. Bush and Barack Obama intended to restore confidence in the system. The only female in the movie who has any lines is a prostitute who asks Mr. Gandolfini's character to zip up her dress before he throws her out of his hotel room. Edited from an interview.

What did Andrew Dominik say to convince you to do this role?

James Gandolfini: I think he said, "Shut up. You're the guy to do this. And you're going to do it." And so after the 900th time he said that, I was like, "OK, I'll do it. Just leave me alone." And I loved the dialogue, but [Mickey] is a disgusting human being. I did some pretty disgusting stuff during "The Sopranos" and I was hesitant to step back into those shoes.

Yet the fact that he was in love somehow made him a little sympathetic.

Yeah, he was in love with a hooker he knew for three weeks, God knows how many years ago. He was fixated on this one thing—and that's the bright spot of his life. He's a pathetic mess who happens to be good at shooting people in the back of the head.

Were you worried about being seen in a bathrobe again—the classic Tony Soprano ensemble?

Yeah, there were some similarities to the world of "The Sopranos," and in a way the character is like Tony Soprano, but he's 20 years older, down the line. That was an interesting thing to play, which I'd never really thought about. He's a different man. He's not as smart. Then from there on, there are a lot of differences in my mind. I don't know what people will see.

One big difference that people will see are those groovy sunglasses. Was that your idea?

Well, I've seen it on people before. It was just something that struck me. But yes, it was my suggestion. It's indicative of an older generation. Let's just say that it puts him in a specific time and place, I think. Andrew grumbled about it in the beginning, but I think he was fine with it.

Brad Pitt has said that watching you act was like watching Brando. What was it like working with him?

I think Brad is being very kind. If you've ever heard me do a Southern accent, that would go right out the window. Brad is one of those guys who gets underrated. Let me start again. If you go through his career he's pretty much done it all. I admire what he does in New Orleans building the houses, how he juggles a lot of stuff. There are some actors you work with and they are that very big actor when you are in the scene. He's not like that. You don't think of him as Brad Pitt. You think of him as this guy. There's none of that movie-star crap. He's a good guy. He's from Oklahoma. I think it's great that Brad really puts himself into these movies, and they're a different kind of movie. It's a wonderful thing.

And what was it like working with Vincent Curatola [who played Johnny Sack in "The Sopranos"] again?

I wasn't in any scenes with him. He was in the hotel right before me. I got there and all anybody ever said to me was, "When's Mr. Vince comin' back?" They didn't give one s— about me.

I enjoyed the film, but it's very violent and very rough. It's for a specific audience.

It is specific. It is a different kind of gangster movie, one that I found more appealing. Because God knows, you've seen the other kind a million times.

Let me just say something about Andrew Dominik. There are very few people who write the movie, direct the movie and edit the movie—it's rare. This is his baby, his blood. Guys like him are rare. ['Sopranos' creator David] Chase is another one. I love that [Mr. Dominik] will tell you that you suck when you suck. No bones about it. I really enjoyed working with him. Brad, the two of them worked together on the "Jesse James" thing.

"Jesse James" didn't do that well at the box office, but Brad's production company still backed him.

He is an artist—the way he cares, the way he's on the set. He'll take longer time with takes, he likes dialogue. Things that open up the movie to interpretation more than the little box studios will put them in. And that's good and bad for the movie. It's great they let him do it, and I think he's a guy who's going to do great stuff.

Write to Rachel Dodes at rachel.dodes@wsj.com