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It’s also a far bigger-scale production for Mr. Pitt and Plan B, and things haven’t gone smoothly. The ending is being reshot — typically a bad sign for a movie — and Mr. Pitt calls the film “a total learning experience for me.” When the film finally wraps, he said, “Believe me, I’ll be celebrating.”

Dede Gardner, Mr. Pitt’s producing partner, said getting older has only made Mr. Pitt more patient.

“He’s extremely careful,” Ms. Gardner said. “I suppose that’s one thing that happens if you age with consciousness, to be vigilant.” Their other coming productions are smaller, more director-driven. Plan B is producing the next film by Steve McQueen (“Shame”), “12 Years a Slave,” and is slated to again produce a film by Mr. Dominik: his planned Marilyn Monroe biopic “Blonde.”

Though “Jesse James” made a scant $4 million at the box office, Mr. Pitt has stuck with the director.

“Somewhere in the late ‘90s, it became clear to me that there were many leading-men roles that you could plug anyone of us into and virtually get the same thing,” Mr. Pitt said. “Because there’s such an investment of time and thought, I wanted to find stories that were more personal to me and that I believed I could add something that was unique.”

“Killing Them Softly,” is certainly that, a film that probably wouldn’t exist if not for Mr. Pitt. It’s an unusual mix of genre — gangsters and guns — and politics. Set in 2008, the fiscal crisis looms large, with speeches by President George W. Bush and President Barack Obama inserted as an obvious metaphor. Mr. Pitt’s character declares: “America isn’t a country. It’s a business.”

Between balletic slow-motion violence, Mr. Dominik stages Higgins’ dialogue in long scenes that give the actors theaterlike room.

Mr. Gandolfini had twice previously worked with Mr. Pitt. “We were both at the beginning of our careers,” Mr. Gandolfini said. “He’s the same guy. He’s a good guy, a regular guy.”

And right now, despite any concerns about “cresting the precipice,” Mr. Pitt exudes contentment. His confidence as an actor is high, he said, attributing his ability to “craftsmanship.”

In his personal life, he and Miss Jolie are planning to marry, after once saying they wouldn’t until gay marriage was legal.

“It’s an exciting prospect, even though for us, we’ve gone further than that,” Mr. Pitt said. “But to concretize it in that way. It actually means more to me than I thought it would. It means a lot to our kids.”

As he approaches 50, Mr. Pitt’s career longevity even surprises him.

“It’s amazing I’ve stuck with this this long because I’m not usually like that. I hit the road,” Mr. Pitt said. “Exploring within it has been the thing that’s kept me in it.”