Ben Affleck’s career trajectory rarely happens in Hollywood much less all by age 38: from unknown actor (Mallrats, Chasing Amy) to Oscar–winning co–writer (Good Will Hunting) to leading man (Armageddon, Pearl Harbor, Changing Lanes, The Sum of All Fears, Daredevil) to tabloid fixture (“Bennifer”) to washed–up star (after Gigli) to budding director (adapting Dennis Lehane’s novel Gone Baby Gone) to hot actor/helmer with the #1 opening movie September 17–19. For The Town, Affleck returns to his Boston roots and blue collar crime to adapt Chuck Hogan’s novel Prince Of Thieves for the big screen. The result: an adult–pleasing hit that has entered the Best Picture discussion. Mike Fleming talks to him about his and The Town‘s Oscar chances:

DEADLINE: So you wrote yourself a second career as a director in Gone Baby Gone. Now you’ve written yourself the edgiest role of your acting career since Good Will Hunting. How much of this was about you wanting to reinvigorate your onscreen career?
BEN AFFLECK: A huge part of this was wanting to play the role. I hadn’t had the chance to play a character as interesting as the one Chuck wrote in the book in a long time. In that sense, it did feel like Good Will Hunting because I was trying to make the movie, in part, as a step in my acting career.

DEADLINE: These R–rated crime dramas with action sometimes get marginalized in Oscar season, but this one has stayed in the conversation. Gone Baby Gone, though lauded, grossed only $35 million worldwide. The Town so far is nearing $150 million worldwide. What has most surprised you about the way it played and the reaction?
AFFLECK: Relative to my first movie, it didn’t have to do that well to be a step forward, so I was set up well. I think people caught up to that movie on DVD, but when you come out and do $20 million at the box office, nobody calls to congratulate you. In terms of pure commercial success, the thing that struck me was, our opening weekend on The Town was bigger than the whole number on Gone Baby Gone. This time, I had very modest expectations and I was really surprised the movie did as well as it did. It’s not a juggernaut, but my big goal was seeing it turn a profit for the studio. I use that as my metric for whether or not they’ll let me direct another movie. I remember calling up and saying, ‘So have you broken even yet? Are you going to make money on this? Are you happy?’ I’m a little embarrassed I’d done that, but it was what I set out to do. And it made me be sure I kept the costs down to under $40 million. This way I could make a movie that dealt with themes that interested me, at a pace I like dramatically.

DEADLINE: What went through your mind as you were deciding whether or not to do this?
AFFLECK: My first thought was, I really wanted to play the role. But I was concerned that the overlap between this and the other movie I directed would be too much, and that I ran the risk of getting pigeonholed for making crime movies in Boston. When I really want to tell stories that take place all over. That made me pause. But there were a couple things that ultimately persuaded me to take on directing it as well. There were a ton of great parts, and I thought the material gave me a shot to work with really good actors. And there was a big challenge in trying to synthesize the two elements of the movie. There was the traditional genre element — the robbery, heist, chase and all that stuff — which had to be done in an interesting and unique way in order to work. That needed to fuse with the character drama on the other side. I felt intimidated and daunted by that challenge, but felt, if I could execute it right, I’d put myself in a position to be able to make movies that I am really interested and attracted to. That is a rare thing in Hollywood. Mostly we’re just schmucks limited by our options.

DEADLINE: What did you do better this time?
AFFLECK: As director, this definitely had a broader scope than my first movie. On a basic level, movies are defined by performances and writing and it’s up to the director to bring those together or screw it up. To some directors, this was a small film, but to me it was a big step forward in budget, scale and the attempt to cross–pollinate these two kinds of movies.

DEADLINE: How difficult was it when the director is also the star?
AFFLECK: Because I was directing myself, I got to make my own determination about what was most interesting about my performance. That’s a double–edged sword. People know it is you making those decisions, so they probably judge it more closely. And it calls into question your perspective on yourself. You put your taste on the line. If you can’t be good in a movie you direct and write, when is it going to happen for you? You can’t make the argument, I didn’t have the opportunity to succeed. The question became, was I sophisticated enough as a director and an actor to capitalize on those opportunities and to understand how to use them? I shot a lot of film on myself, trying different things and basically directing myself in the editing room when I put the performance together. I read somewhere that De Niro did the same thing on The Good Shepherd. I don’t know if it was true or not but the idea was reassuring. If I was going to fail, at least I would fail emulating De Niro. The approach proved to be, for me, really smart. You gain much more perspective on yourself in the cold dark of the editing room than you do on the set, trying to modulate your own performance along with everything else.

DEADLINE: You’ve hit the highs as an actor, been in gigantic blockbusters like Armageddon and Pearl Harbor, but you hit some low lows in your career, too. Instead of blaming your agent and getting a new one, or feeling sorry for yourself, you literally scripted a resurgence as a writer and director. What gave you the courage to say, I can do this?
AFFLECK: I don’t know. Maybe it’s not being smart enough to know better and say to yourself, what do you think you’re doing? For me, there was a lesson in Good Will Hunting, and even earlier in the things we were taught in the acting school we went to. Generating your own material is the only thing you can rely on. Opportunities come and go, things go well and dry up. But ultimately you have to be responsible for yourself, your life and your career. This wasn’t necessarily a question of nerve or drive, because a lot of people in Hollywood have that. It’s really a question, will you get the break? I’d felt for some time that I wanted to direct and I’d done some writing, and I wanted to continue down that road. I just didn’t know if I would get hold of the right material, or come up with the right idea, and, if I did, would people be receptive to it? The only reason Gone Baby Gone got made was that Dick Cook was willing to pick it up in turnaround. But I’d done a lap around the track at this point, seen the highs and lows, and seen various versions of how things can turn out. If I’ve learned anything through that, it’s that a lot of what you get caught up in doesn’t mean anything. What you really have to be concerned about is your own work, and working hard. And that’s it. Here, I was grateful to have Jeff Robinov really believe in me, and Sue Kroll who I think is the reason why the movie was successful, and Alan Horn green lighting it. Robinov said, ‘I want to hire you, I believe in you, you’re going to have this much money to do it, cast who you want’. I just kept thinking, has he mistaken me for some proven filmmaker? But I do believe in myself. Any artistic endeavor has got risk in it and they’re not all going to fall the right way, no matter how hard you work. A big part of it for me was not getting discouraged, and believing that, if I just had the chance to keep taking swings, I could be successful at some point.

DEADLINE: Your films display an understanding of the under-class, and the working class and through that you’ve established your wheelhouse. Then there were rumors you considered directing Superman, which went to Zack Snyder. What factors do you consider in where to go next? Do you need to do a mega–budget film as a director?
AFFLECK: The one benefit of having done all kinds of movies as an actor is, you learn the pros and cons of being tempted to do a really big movie because it costs a lot of money. With Superman, I think they’re going to do a great version. Chris Nolan is brilliant and they’ve got a great director for it. I’ve love to do something like Blade Runner, but a lesson I’ve learned is to not look at movies based on budget, how much they’ll spend on effects, or where they will shoot. Story is what’s important. Also, there are a lot of guys ahead of me on the list to do epic effects movies.

DEADLINE: If there is an Oscar nomination for The Town, how much does the film owe The Departed for making it okay to consider an R–rated crime drama? Should this genre get more respect during awards season?
AFFLECK: It’s easy to lump movies like these together. My movie owes a lot to The Departed, it owes a lot to Mystic River, and it owes a lot to Heat. Also The Friends of Eddie Coyle. All are R–rated movies in that same vein, and the movies I used as the gold standard of success here.

DEADLINE: You’ve been part of two films that had magical Oscar night results, in Good Will Hunting and Shakespeare in Love. What are your best memories?
AFFLECK: The great memory of Good Will Hunting was going to the Oscars with Matt, and it all being really new. Then we sat down and we were mentioned in Billy Crystal’s opening monologue. That was the biggest deal to us, this iconic guy, in his iconic role as host of the Oscars, mentioning us. It felt like stepping through the looking glass, where you are sitting at home watching television and all of a sudden the television starts talking to you. And then we won and that was a great highlight, something that was hard for us to even absorb at that age. I was 25.

DEADLINE: How about Shakespeare in Love?
AFFLECK: Wonderful, just being part of that large group, like a football team. I felt like the guy on the end of the bench of a championship team. It was just fun to be included. The fact it won stunned me.

DEADLINE: Many still can’t believe it bested Saving Private Ryan.
AFFLECK: Saving Private Ryan is an astounding movie. That opening sequence really changed forever how people shot action sequences. It redefined the genre of intense, powerful filmmaking. That debate is emblematic of what I like about movies. It’s just a matter of what touches you, and that’s what makes movies so wonderful.