The actor-turned-director talks about reinventing himself and his new heist thriller

By Chris Nashawaty
Updated September 09, 2010 at 04:00 AM EDT

Ben Affleck has been at this crossroads before—and knows it. Back in the mid-’90s, he and Matt Damon found their acting careers going nowhere, so they decided to create their own luck. They wrote the screenplay for Good Will Hunting out of equal parts ignorance, hubris, and sheer frustration. Their gamble became one of the most unlikely—and PR-ready— Horatio Alger stories Hollywood’s ever seen. In a town where the main business is scripting fairy-tale endings, even this seemed far-fetched: They sold their screenplay for $600,000, landed the lead roles in the film, and ended up leaping on stage at the Shrine Auditorium, accepting the Oscar for Best Original Screenplay. They looked like a couple of kids who’d hit the Powerball jackpot.

“We looked like a couple of idiots is what we looked like,” says Affleck, laughing.

Affleck turned 38 last month, and despite some gray in his hair, he looks like he’s in the best shape of his life. It’s 10 a.m., and he’s sitting in a beachfront Santa Monica restaurant wolfing down an egg-white omelet. When he cracks up remembering himself on stage with Damon—two Boston boys who’d somehow managed to crash the A-list party—tiny bits of omelet shrapnel fly out of his mouth and land on the table between us.

In theory, I’m here to talk to Affleck about his latest film, The Town—a gritty Boston heist thriller that he not only stars in but directed and co-wrote. (The movie, rated R, opens on Sept. 17.) After a few minutes, though, I realize that what Affleck really wants to discuss is the launch of Ben 2.0—his transformation from box office whipping boy into genuine filmmaker. “That moment—before Good Will Hunting—and this moment now are really similar periods in my life,” he says. “Good Will Hunting was a sort of Hail Mary idea, where we were young enough not to realize how foolish it was. And now, with this second period of my life, I wanted to start over. I wanted to reboot my career.”

It’s an interesting choice of words: “reboot.” It’s one of those slick, slangy Hollywood terms, like saying ”boffo” to describe pix that click in the stix. What Affleck means, of course, is that he wouldn’t mind erasing some of the uglier patches from his résumé. In the first act of his career, he was the guy who seemed to have it all but then somehow blew it. He began acting in the early ’90s with small turns in School Ties and Dazed and Confused. He soon graduated to bigger parts in indie hits like Chasing Amy and Good Will Hunting, and then the movies got bigger—probably too big. Pearl Harbor. Daredevil. Gigli. The aptly titled Paycheck. On screen, Affleck became a punchline. Off screen, he’d turned into something worse: a tabloid casualty, thanks to a stint in rehab in 2001 and his high-profile relationship with Gigli costar Jennifer Lopez. People saw him as half of ”Bennifer”—gossip fodder first, and a serious actor second…if at all. “I was definitely frustrated and wanted to withdraw from a part of my life that I was starting to hate,” he says. “I was caught in that intersection of celebrity and tabloid culture, and it was beginning to upstage the movies I was trying to do.”

That’s when Affleck started thinking seriously about stepping behind the camera. “It was the only option I felt I had to do good work, because the quality of scripts I was seeing was just getting worse and worse. I felt like I was either going to believe in myself and try directing, or just give in. And I decided, ‘I am going to walk the plank, and maybe there will be sharks and maybe there won’t.’”

Affleck made his directorial debut with 2007’s Gone Baby Gone. The tense and twisty adaptation of Dennis Lehane’s South Boston-set novel got great reviews, gave his little brother Casey his first major leading role, and drew an Oscar nomination for Amy Ryan. Overnight, critics and moviegoers were forced to rethink the guy they thought they had all figured out. (His terrific and unexpected performance in 2006’s Hollywoodland didn’t hurt either.) Ryan says that when Affleck was directing Gone Baby Gone, what most impressed her was how he treated the nonprofessional actors on the set. “Ben has great compassion, and he’s so positive,” she says. “Some of the locals who were cast in the film, they’d never acted before, and so they might be way off the mark. And Ben would kill them with kindness. ‘That was great! Now can you try it like this?’ He always built everybody up. And that’s how you get great performances.”

Now comes act 2 of his reinvention. The Town is an ambitious and action-packed film that will likely cement him as a legitimate and talented filmmaker. And this time around, Affleck isn’t doing surprising work just behind the camera but in front of it, too. He plays a conflicted bank robber from the blue-collar Charlestown section of Boston who’s torn between his loyalty to his brutal, hair-trigger crew and his desire to go straight. Thanks to bareknuckle performances from Affleck, The Hurt Locker’s Jeremy Renner, and Mad Men’s Jon Hamm, The Town is already sparking buzz that it could be an Oscar contender in the mold of Mystic River and The Departed—something that surprises no one more than Affleck. “My thinking was, I don’t want to do anything for money, because I’ve certainly worked for money at times. And if that means I don’t work, then I don’t work. Luckily, on both of the films I’ve directed, some really great actors have wanted to work with me. I don’t know why. I’m not sure I would have worked with me!”

Affleck uncorks another of his likable guy’s-guy laughs… until something across the restaurant catches his eye. “Is that Lindsay Lohan?” he asks. Yes, it most certainly is. Affleck doesn’t seem particularly excited by the celebrity sighting. In fact, he seems to slump down ever so slightly in his chair, perhaps trying to disappear so she won’t come over to say hello.

When the coast appears to be clear, Affleck picks back up, talking about how badly he wants to prove to people (including himself) that Gone Baby Gone wasn’t a fluke, that he has more than one good film in him as a director. He knows that some people might look at The Town and think he can make movies only about Boston. But he doesn’t care. After Affleck read the script for The Town, he simply couldn’t shake it. He began talking to real-life FBI agents and Charlestown criminals who’d done hard time, fine-tuned the screenplay (peppering it with true-crime tales he’d heard), and got $35 million from Warner Bros. to make his film. That may not sound like much money, but Affleck seems to prefer working in stealth mode: “I’m sure it’s one of the smallest movies Warner made this year. Which is great, because you don’t get as much scrutiny as Harry Potter. Although I’m sure the Harry Potter folks have it figured out by now.”

As he says this, Affleck’s cell phone starts humming. He looks at it and says he has to cut the interview short. His wife, Jennifer Garner, is out of town, and their two daughters are flying back to L.A. this morning with their nanny. Affleck has to pick them up at the airport. “I’m Mr. Mom,” he says, apologizing over and over. “It’s not the coolest thing, but what are you going to do? It’s life. It’s the real thing.”

When Affleck calls the next day, he apologizes again. This time, for dwelling so much the day before on his career frustrations. I tell him not to worry—that there are probably some EW readers still smarting from Gigli who will appreciate the sentiment. He laughs. “Thanks, man. You’ve got to help me out in this article. You’ve got to help me sell the new movie. Don’t write endlessly about Gigli. I understand it has to be in there, but?”

Switching topics, I ask what a typical morning is like at home, and what sort of impact getting married and starting a family has had on his quest to reboot. Silence. “Well, I like to sort of maintain my privacy on that stuff,” he says. “But hopefully you get a little bit more mature. You get perspective. My wife is a world-class mom. We understand that being parents is the most important job we have. And she still manages to be beautiful and sexy, and I don’t know how she does it, and I’m not going to ask questions.” He laughs again, and I wonder if there’s any food flying out of his mouth on the other end of the phone.

Twenty-four hours ago, Affleck seemed contrite about the films he regrets. Today, he focuses on the ones he likes: “ Good Will Hunting, Chasing Amy, Boiler Room, this little movie called Going All the Way, Changing Lanes, Extract I loved,” he says, referring to the 2009 Mike Judge comedy that seemed to be on DVD even before its opening weekend was over. “I probably got the best reviews of my life on that one. I don’t know what that says, because the movie didn’t make any money, but a lot of movies I like don’t make money.”

Affleck hopes that The Town isn’t one of those noble failures that critics admire but no one goes to see. For one thing, he wants to be able to keep directing movies. For another, it’s a personal story about the city he grew up in and, for the first time in his professional life, there’s no one else to take the hit if it tanks. “It’s kind of hard to disavow a movie when you’re the actor, writer, and director,” he says. “You’re definitely all in.”

For a long time, Affleck wasn’t sure he’d be able to keep all three balls in the air. He wasn’t alone, either. “At the end of my audition, I remember asking Ben, ‘How do you know you can direct and star in this thing?’” recalls Renner. “And his answer was what made me do the movie. He said, ‘I don’t know.’ Ben’s taken a lot of flak for s—. But this movie will establish him as a serious filmmaker.” Hamm agrees: “Ben is intelligent and curious. And I think that combination has let him pick up directing so quickly. As an actor-turned-director, he’s just way more familiar with what the actors are going through.”

One thing that impressed Affleck’s costars was how, as with Gone Baby Gone, he studded the cast of The Town with working-class locals and ex-cons with chowder-thick accents. Affleck admits that the bit players not only lent authenticity but also helped the pros give better, richer performances. “I’ve developed higher standards,” Affleck says. “It’s something I learned late. I guess I’m a late bloomer, which is too bad for a guy who has success young. But fear is a great motivator. You have to be fighting all the time and work as hard as you’ve ever worked. I learned that the hard way.”

When Affleck says things like this, it feels like he’s speaking to himself, trying to remember not to take his career for granted. To be choosier. Next month, for example, he’ll star in The Company Men, a timely drama about corporate downsizing. He also just signed on to star in Badlands director Terrence Malick’s top secret next film, opposite Rachel Weisz. “Malick is one of the geniuses,” he says excitedly. “It’s like when you look at Matt [Damon], he’s had such a wonderful career because he’s a great actor, but he’s also had the greatest apprenticeship in the history of cinema if you look at the directors he’s worked with.”

Hearing Affleck say something so hopeful kind of comes as a shock. And to be honest, it’s a bit of a relief. Sure, he’s made a few bad movies. Eighteen years and 40 films into a career, who hasn’t? But by all appearances, his reboot seems like a boffo success. “Yeah, life is pretty good right now,” he says. “I don’t do movies that make $300 million, but I’m happier than I’ve ever been. I’m extremely lucky in my family. I’m married to this incredible woman. I’m not sure I did anything to deserve winding up here, but I’m not going to do anything to f— it up.”