The Oral History of ‘The Town’

Chuck Hogan’s novel Prince of Thieves opens with a toast:

Raise a Glass. Solemn now:

To The Town.

To Charlestown, our one square mile of brick and cobblestone. Neighborhood of Boston, yet lopped off every map of the city like a bastard cropped out of a happy family portrait.

Ben Affleck grew up in Cambridge, only a few miles away from Charlestown, but to him the distance between the two places felt vast. Unfair or not, Charlestown had a reputation. “It was like a different world,” the actor and filmmaker says. “When I was a kid, I was scared to go there. Violence, unsolved murders ...”

And armed robbery.

In 1995, The Boston Globe reported that the neighborhood was “a community to which more armored car robbers are traced than any other in the country, according to FBI statistics.” Hogan recalls reading that and filing it away. It later served as inspiration for the Massachusetts native’s third book. Published in 2004 and set in the ’90s, it follows a team of stick-up men led by Doug MacRay, a washed-up NHL draft pick and recovering addict whose traumatic childhood has led him to follow his incarcerated father into the family business.

The story appealed to Affleck. A decade after establishing his Boston bona fides by cowriting and appearing in Good Will Hunting with Matt Damon, he was offered a chance to adapt Prince of Thieves for the screen. “It was concealing a character-based drama centered around themes that I was interested in, particularly the theme of children paying for the sins of their parents,” Affleck says. “But wrapping that in the sort of candy shell of a heist movie.” Beyond the flashy heists, The Town—renamed because Prince of Thieves had already been used as the subtitle of Kevin Costner’s version of Robin Hood—is a movie about fate, loyalty, and morality, and how those things commingle. MacRay is pulled between the devil and angel who sit on his shoulders: Jem, who spent nine years in prison for killing someone who was supposedly planning to kill Doug; and Claire, the bank manager Doug falls for after a job.

In so many ways, the project came along at the exact right time. In the 2000s, critically acclaimed, Irish American–centered crime dramas like Clint Eastwood’s Mystic River, Martin Scorsese’s The Departed, and Affleck’s Gone Baby Gone had turned the Massachusetts capital into a Hollywood hot spot. “I call them ‘No R’ movies,” Hogan says. “Not ‘noir,’ French for black. But ‘No R.’”

Because of oversaturation in the last decade, Boston movies have been rightfully skewered. Affleck unequivocally contributed to that proliferation. The imitators that his opus spawned, however, couldn’t recreate what he managed to. With the premiere of The Town 10 years ago, the “No R” genre peaked. Affleck didn’t just direct, he played the lead alongside a cast of present and future superstars and locals. With a relatively modest budget of $37 million, he made a classic heist flick that’s well, porn for New Englanders: the heavy Boston accents; the scene in a Dunkin’ Donuts; and, oh yeah, the fact that a crew of robbers takes down Fenway Park.

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Part 1: “You Just Have to Add Something to It”

In addition to including the statistic about Charlestown’s armed-robbery predilection, the preface of Prince of Thieves features a quote in The Globe by an anonymous Townie. “I’m mighty proud of where I come from,” he says. “It’s ruined my life, literally, but I’m proud.”

Chuck Hogan (author, Prince of Thieves): When the book came out, I was scheduled to do a reading at the Charlestown Public Library. I remember the librarians called me the day before, just to confirm. And they were like, “Just so you know, we’ve had some calls and threats of violence.” People didn’t know what the book was, I think they were expecting something that would really knock Charlestown. I showed up, I did the reading. Everybody in attendance loved it; no car windows smashed or anything like that. But as I was signing books afterwards, I see this guy coming up. He’s maybe four people away. The top of his head was really messed up. He had really bad scars. He was with his mother. He came over and he was a little bit shy but she was speaking for him. He was in his early 20s. But he pointed out the quote. He was like, “That’s me. That’s my quote that you used in the book.” I was like, “Oh man, what’s up?” He was excited.

Peter Craig (cowriter): There’s a really great detail that I always loved where Doug just sticks his gun in one of those portholes in the armored car, and so the bullets like ricochet and rattle around in there. And that looks like a detail you’d come up with writing a script. It was actually in the book. Chuck gets credit for that. Chuck’s such a good writer that you get the tone from his details.

Hogan: Dick Wolf from Law & Order somehow read [the book] early. He loved it, optioned it. There was a script written. I don’t know exactly what happened, but I know that the option was running out. And I got a call saying that [Fatal Attraction and Indecent Proposal director] Adrian Lyne had read it and really wanted to do something with it. He didn’t want to option it himself, so they set him up with [producer] Graham King, who got the option. And so Adrian developed it for quite some time.

[Adrian Lyne did not respond to a request to be interviewed for this article.]

Craig: I was a struggling crime writer. Adrian had wanted to do one of my books, which was kind of unadaptable because it took place over like, 30 years. It really wasn’t gonna work. But he also liked this book by Chuck Hogan. And he got really excited.

Hogan: Adrian really thought in more operatic terms, and he really wanted to do the book. The full version.

Craig: Adrian was at this really ambitious double-album phase of his career, and he didn’t want to cut anything. He saw it and he was like, “This is perfect. This is the script I want.” And I said, “Adrian, this is gonna be a three-and-a-half-hour movie.” He’s like, “Well, if Scorsese can make a three-and-a-half-hour movie, I want to.”

Ben Affleck (director/star): He had an adaptation that was very, very different and it was really focused on the love story. It was really more of an erotic thriller: The criminal who falls in love with the captive kind of thing.

Craig: Adrian wanted 90 shooting days and $90 [million] to do it. By the way? I love Adrian.

Hogan: Warner Bros. didn’t want to make the movie for that amount.

Craig: [Jeff] Robinov, [the president] at Warners, really wanted to make the movie. At one point we even had Brad Pitt ready to do it … so it was really close. [But] Warners gave it back to Adrian and said, “You know what, shop it around.” He took it to Imagine; he took it to Universal. They were about to buy it but they wanted to cut it, too. Everybody wanted to cut it. It eventually just blew up. Adrian was off the project.

Warner Bros.

Affleck: Jeff Robinov and [worldwide marketing president] Sue Kroll were working at Warner Bros. at the time, and they asked to have a meeting with me. They had seen Gone Baby Gone, which opened in like sixth place to $5 million or something and wasn’t seen widely. But they liked it and they wanted to meet with me, and I was like, “of course.” I was willing to meet with anyone who was interested in hiring me as a director. And they said, “We like what you did, we think you’re a good director and we believe in you.” And I was kind of struck by the enthusiasm they had considering for the most part, Hollywood operates based on success. Particularly commercial success. But they said, “We have this project that we think you’d be right for. It’s been in development here for a while. The budget that we had previously was too high for us to make it.” And then I realized, “Maybe they think I can make movies more on the cheap.”

I was fine with that. I’d made Gone Baby Gone for $18 million. It’s not a super cheap movie but it’s not expensive like a studio movie. And so they said they had this script based on this book, and I said, “OK, let me look at it.” I read the adaptation, and it had been developed by Adrian Lyne, who I just worked with.

Hogan: I was just checking out the internet one day in my office and I saw a Variety headline: “Affleck moves to The Town.” I called my wife over and said, “I think they’re making a movie of the book.” And that was it.

Aaron Stockard (cowriter): Ben called me up and said, “I know what I want to direct next. It’s this movie and it’s already got a script. Which I like, and it’s good, but I want to sort of put our perspective on it.”

Affleck: What I liked about [the book] was that it was similar to [Dennis Lehane’s] Gone, Baby, Gone in that I both could use the bones and the structure of the story and there was good dialogue and interesting characters in there, but also they kind of inspired me to create more and add on to it. I’ve never felt all that interested in literally translating from book to page. Then it might as well just stay a book. If you’re gonna make a film of it, you have to add something to it, or try to. I thought I had something to add to it. And obviously it was in Boston—that I was comfortable with.

Stockard: As much as it felt like, “We know this story, we know these people,” there was also this entire world for us to discover.

Affleck: I [set] that movie in the 2000s, but it was really about the ’80s and ’90s in Charlestown. I sort of pretended that Charlestown was still the way it used to be. But it really wasn’t. It was taking a period of time that had passed and pretending it was still a reality.

Stockard: Obviously you’re making a movie so you mythologize it a little bit. But it was very real.

Affleck: I was able to get access to the FBI and the division that chased and caught most of these armored car robbers, particularly in Charlestown.

Stockard: Ben and I went and spent a day with this FBI task force. And they told us all these stories, and all these fascinating things, and built up what this mythology was. Ben wasn’t in Boston. He flew in. We went back to his hotel room right after. And I remember immediately getting on Google Maps and looking at the North End, because they had described a robbery that had taken place [there], and being like, “They robbed this thing here, and they had to get to that bridge there.” So we basically mapped out where this little route was. “What’s the best way to get there?”

Chay Carter (coproducer): We found a couple of real bank robbers that we did real research with, which is what these four [thieves] were based on. They’re incarcerated.

Affleck: That was fascinating. That’s where I got my best stuff.

Carter: Ben actually went and sat down with the guy that his character was based on, and was able to see him and take notes in person. Well, not take notes, because you couldn’t bring in a pencil.

Affleck: My favorite moment in the movie, cinematically, came directly from a conversation I had with a guy who was in MCI-Norfolk at the time. He was doing a long sentence. He’s probably still there. He had participated in a bunch of these armored car robberies, and we had been talking for two hours, and time was almost up. And I said, “Is there anything just weird or strange or unexpected or bizarre in the course of this?” And I mean, the guy had lived a pretty bizarre life. And he said, “Well, there was a time I remember when we all had just robbed a truck and we pulled up to the switch car, and we all had our masks, and we were carrying a bag of money, and we pull up to the car, and we look over, and there’s a cop doing ‘lazy construction.’ And he just looked at us, and we looked at him, and he looked the other way. And we got in the car and kept going.’” I totally put that directly in the movie.

Part 2: “I Wanted a Guy Who Was Really Unpredictable and Scary.”

When it came time to cast The Town, Affleck had fun putting together a star-powered ensemble on a relatively limited budget. He also made sure to populate the movie with people who didn’t have to fake their Boston accents.

Affleck: Because it was the first time I was gonna star and direct, and because I didn’t have a lot of money to pay a bunch of stars, I had the luxury of being able to just cast the best actors. If possible, it’s really great to hire people with whom an audience isn’t overly familiar, because audiences have developed expectations and kind of anticipate what an actor might do if they’ve seen them a bunch. For example, with my brother [Casey] in Gone Baby Gone, I thought it really benefited from the fact that he wasn’t so well-known. You weren’t sure exactly what he was gonna do, or how he was gonna behave, because it wasn’t Matt Damon, who’s always the hero and always wins out in the end. Jason Bourne kills the bad guys.

Jon Hamm (FBI special agent Adam Frawley): I knew he had some serious Boston cred. So I read this new version of the script. First of all, it was about 20 pages shorter. The story was much clearer and cleaner. It just read like a good old-fashioned, kind of ’70s cop movie, where the good guys are the bad guys and the bad guys are the good guys.

Rebecca Hall (Claire): I remember I had to fly to New York to meet Ben because I was based in London at the time, in the middle of this theater tour. I wasn’t really in the movie world. It all felt sort of very impossible and glamorous. And Ben Affleck was incredibly famous already. He’s been forever. In my imagination, he’s always been Ben Affleck.

Titus Welliver (Officer Dino Ciampa): I called the production office and I got [Carter] on the phone and I pretended I was a Boston detective. I said, “Look, you know, I understand that you’re making this movie about robbers out of Charlestown. I’ve been on the force for 20 years and I’m not looking for money or anything, but I’m originally from Charlestown and I think I could be helpful.” She’s like, “Well, it’s really great to talk to you, we do have technical advisers and everything kind of lined up, but if you wanted to drop off a card or something like that.” I said, “Yeah, yeah, sure, sure. I’ll do that.”

My place in Connecticut is only three hours from Boston, so I just, on a whim, jumped in the car, drove up to Boston, went to the production office and walked in, and David Crockett, one of the producers, and Chay were like, “Hey, what are you doing?” And I said to Chay, “Oh, I’m Detective such and such.” And she was like, “You fucker.” I said, “Is he here?” And she said, “Yeah, he’s down doing auditions downstairs.”

I kind of slipped in and waited in line and then said to the production assistant, “Don’t say my name. Just let me go in.” She opened the door and I just walked in and Ben was there and he just burst out laughing. I said, “Really, I’ve got to drive all the way to fucking Boston to get a meeting with you?” He looked at me and went, “You’re crazy.” I said, “No, I’m not.” He said, “So, you really want to be in this film?” I went, “Yeah.” And then he went, “Dino?” I went, “Yeah.” He went, “OK. You could’ve just called me.”

Warner Bros.

Chris Cooper (Stephen MacRay): Ben had me at “prison.” It was great. I wanted to be a part of that. I knew it was one scene and it was gonna be an important scene: [Doug’s] relationship with his father.

Affleck: Blake Lively took the train from New York. She was doing Gossip Girl, which at the time people thought like, “Oh, that’s just a CW Y.A. soap.”

David Crockett (producer): They read, and not saying who she was or what she was in, she did the [Boston] accent. She prepped for that for God knows how long.

[Lively did not respond to a request to be interviewed for this article.]

Affleck: Having been through an experience myself where I felt that people had a sense of me that wasn’t really fair, I’m very sympathetic to and interested in people who are, I think, sort of pigeonholed. Blake came in and read the scene and was amazing. And I thought, “Not only is she the best actress for the part, she’s gonna be able to really surprise people.”

In one of his final roles, Academy Award–nominated English actor Pete Postlethwaite plays Fergus “Fergie” Colm, a menacing mob boss/florist who gives Doug orders while chomping gum and stripping roses.

Hamm: I got to meet Pete Postlewaite, rest in peace, at the hotel bar. There’s like four people in the whole bar, which is a huge bar. I look over and it’s Pete, and he’s having his breakfast, and he’s reading the paper, and I hadn’t met him before because I didn’t have any scenes with him. But I certainly was familiar with his work. And I just came over to him and I was biting my tongue. There’s two ways that this can go. It can be a terrible experience, meaning you can interrupt somebody when they’re trying to have a nice moment, or they can be pleasant. I said, “I’m so sorry to bother you Mr. Postlethwaite, but I’m on the movie, sorry we don’t have any scenes together, but I’m so excited to be in a movie with you.” I gushed for a while, and he just smiled as broad as he could, and he’s like, “Come on, come on, sit down, have a drink.” I was like, “Well, it’s 11 in the morning.”

Crockett: Pete had a reputation for being kind of a hardass. And a lot of older actors, [when they’re] told, “Go here, do this,” a lot of these guys are like, “Fuck off. I’ll tell you what I’m gonna do.” And so we were a little bit extra, extra respectful. He was not doing great [health-wise]. But he could not have been happier to be there.

Affleck’s crew of bank robbers needed genuine local flavor. They had to look and sound like they just rolled out of Old Sully’s at 2 a.m. on a Sunday. The actor who played James “Jem” Coughlin, Doug’s ex-con buddy, however, wasn’t from Boston. Although it certainly felt like he was.

Owen Burke (Desmond Elden): I was going to a community college in Charlestown, I was working under the table, I had just gotten past some legal trouble in my teenage years.

Slaine (Albert “Gloansy” Magloan): I was born in Dorchester, grew up there as a kid. I lived in South Boston, Roslindale. As I got older I lived in [Jamaica Plain], West Roxbury, where my son was born.

Burke: I was at a point where I was still looking for what I was gonna do with my life. They happened to be casting this action movie across the street from where I live. My father insisted that I go over. He said, “They’re looking for guys like you.” And so I went over and I read a few lines, they took my picture. And then a few months later I got a call and they were like, “Oh, we want you to come back in and audition for the director.” I show up at this office in Cambridge to go in and read and all of a sudden I see Ben Affleck walk in. And I’m like, “Whoa, so he must be the director.”

Slaine: When he cast me in Gone Baby Gone I had no acting experience—and I wasn’t the only one.

Burke: It was not on my radar at all. I had never even been in a drama class or nothing like that.

Slaine: I think he was just really going for authenticity.

Crockett: He knew from the beginning that [Magloan] was gonna be Slaine. The funny thing is—and I found this out later—he met John Cena for that role. They’re both from Boston and they’re doing the whole Boston thing, and Ben being Ben, in a very playful way, tries to like, wrestle him. But John is obviously a much bigger guy. The way John tells the story is, “Of course I do two [moves] on him and I’ve got him and he can’t move,” and [Affleck’s] like, “alright, alright, alright!”

Affleck: The hothead friend. That was the most important part, because he could so easily lapse into cliché. When it’s done great it’s Joe Pesci in Goodfellas. When it’s not, it’s predictable and obvious and trite. I didn’t know, physically, how I wanted the character, but I knew that I wanted a guy who was really unpredictable and scary and you felt nervous when they were on screen. Like you didn’t know what they were gonna do.

Carter: They were looking at Chris Pine in the very beginning, because of course Star Trek had just come out.

Affleck: With Jeremy Renner, somebody said to me, “There’s this guy, he’s got this movie coming out that you should see, it’s supposed to be really good. It’s called The Hurt Locker.” The only thing that I had seen of him was the Jeffrey Dahmer movie, which couldn’t have been more different from what I wanted.

Hamm: I had also seen Dahmer. And I was like, “Who the hell is this guy? He’s crazy.” He’s from Modesto, and he’s kind of got that bulldog, kind of dirtbag sensibility.

Affleck: Jeremy came in and was just awesome. He had the beginnings of the accent, clearly he had the ability to do it—a bad Boston accent would ruin that part. And he read and blew me away.

[Through a representative, Renner declined to be interviewed for this article.]

Hamm: It was impressive. He was able to hold his own with a lot of those dudes who are the real deal.

Affleck: The attitude in that scene where [Jem] shows up and discovers me with Claire, in front of Grendel’s in Cambridge, and the audience knows what he knows, but she doesn’t know, and I know that he’s discovered me ...

Hall: Jeremy Renner’s character was just so brilliant and frightening. One of those characters you love to hate and find sort of intoxicating and moving; all of those things at the same time.

Affleck: He played that so deftly, and made that scene work so well, when he’s sort of smiling and laughing, but there’s so much menace underneath it.

Hall: I just remember him being so mercurial. So unexpected. Every take had the same amount of tension and edge but it was just all over the place. And in an exciting way. You didn’t really know what was coming. And that was really thrilling to respond to. He gave me so much ammunition all the time to play off and to feel. He made my job easy.

Welliver: [Renner] switches it on and I love watching him work. I remember one day going to set because he and Ben were doing that great scene where it ends up with them having a fight.

Cooper: I don’t know Jeremy’s height, but Ben is a pretty big boy. And man, he stood up really well to Ben.

Welliver: On the page it was one thing, and he beat the page because rather than it being a scene that was about anger and aggression, Renner turned that scene into a scene about heartbreak and devastation. That’s the one moment that gives you a glimpse into how damaged and how profoundly broken Jem is.

Cooper: I think he was just having a ball with this character.

Crockett: I vividly remember it. It’s Renner’s Oscar moment.

Part 3: “You’re Born in Charlestown, You Play Fucking Hockey and You Rob.”

Referring to a location as a vital character in a movie is a cliché, but in the case of The Town, it’s impossible not to. An alternate title for the film could be Ben Affleck’s Boston, and no one would have had it any other way.

Affleck: In a world of increasing homogenization, having this fresh place that I think stood out, it was appealing. In the ’70s, New York was that. Everyone was making New York movies.

Welliver: If anything, people were kind of burned out on the New York gangster genre.

Affleck: There have been a lot more New York city movies than there have Boston, for sure. I feel like we’re still in the black.

Welliver: He said, “Hey, we’ve got great stories in this city that nobody’s telling.”

Affleck: It’s parochial and kind of a small town in some ways. It’s kind of insular.

Hamm: He is a favorite son of Boston for a very good reason. I could tell it was hard on Ben because literally going out to dinner was not really an option.

Carter: He’s 6-foot-3. He’s not someone that blends in easily.

Hall: You’d be shooting this tiny little intimate scene, Ben and I, and I’d look to my left and there were but thousands of people watching the set. Thousands. You don’t know where they come from. It would go from completely quiet at 5 o’clock in the morning to suddenly it’s like doing theater on a massive scale. Everywhere we went people were so excited to see him. He has a certain thing in that town.

Welliver: It [was] like doing photo shoots in front of Graceland with Elvis when Elvis was still alive.

Hall: It was like being alongside Prince Harry and Meghan Markle in London.

Hamm: We could all go, hang out at the bar; me and Rebecca, and Renner, and Titus, that whole crowd. You’ve got nothing to do, it’s like, “Let’s go try out an awesome restaurant.” I felt bad that Ben didn’t get to have that experience.

Warner Bros.

Welliver: The upside of that is everybody is rooting for him. They’re so proud of him and they’re so happy. That’s the thing, that there’s a kind of ownership and it’s beautiful.

Crockett: I remember being on the streets of Charlestown talking to some people. Ben’s standing there and he’s doing his public relations things, and people are swarming him. And I was talking to people right next to him. And I said, “Yeah, it’s just so great that he can come back and do this and dig in. It’s just great that he’s from here and he’s back.” And this woman looked at me and she’s like, “He’s not from heah!” OK, he’s from, like, three miles away.

Hamm: Another smart move by Ben was to populate this movie with people that have an actual, real-life connection to these things. We had bank robbers, we had career criminals, people that couldn’t show up certain days because they’d be violating their parole.

Carter: There was a guy, Joe Lawler, who was helping us. He had robbed a couple of banks in Boston years before. He’d done his time. And then he was out, so we were using him again for research. We’re like, “Wait, he’s about the right size, height, and all that other, he could be Ben’s stand-in. It’d be good to have him around for authenticity.” He’s in the movie. He’s part of John Hamm’s FBI crew.

Cooper: I wanted to spend some time in Walpole [at MCI–Cedar Junction] and just observe. They set up a date and Jeremy Renner and I both arrived at Walpole to go through the screening. There are three tiers of cells. The length of them runs, I would think, like 150 feet. And they walked me over to this locked door and once you opened it, there was an old, dusty cobwebby circular staircase. And they led me into this little alleyway. What it allowed me to do is privately observe the prison population. I was up there for what I’m sure was a good half hour. To observe this life. Needless to say, it really shook me up. Good God, some of them may still be there today.

Welliver: The character Dino was a cop who grew up in Charlestown. When we started, I said, “I need a driver who’s Charlestown born and bred.” Interestingly enough, my driver was a guy named John Fidler who was a major suspect in many bank robberies, and also bread truck robberies. I had an interesting moment with him at one point, we were in the car and I said, “What’s the deal?” And he called me Ty, as all the guys did because they didn’t want to say Titus. He goes, “Yeah, you know, I’ll tell you, Ty. Here’s how it works in fucking Charlestown: You’re born in Charlestown, you play fucking hockey and you rob.” And I went, “OK, that sums it up.”

Affleck: Hockey’s such a big thing in Charlestown.

Susan Matheson (costume designer): Ben at one point wears a zip-up track jacket that looks like a Bruins jacket. But it isn’t. We did not have legal clearance to use the logo.

Affleck: The Bruins have been extremely shortsighted and wrong with their policy, where if there’s swearing or violence, you can’t use their logo.

Matheson: I will never forget sitting there with some felt and scissors at 3 or 4 in the morning. I was cutting out pieces of felt while Gina [Rhodes] was stitching them—making, by hand, the fake Bruins logo. It had to feel like Bruins. But it couldn’t be Bruins.

Affleck: I’m like, “Why the fuck do you think people go to hockey games?” Swearing and fighting. It’s like 50 percent of why people buy tickets.

Part 3.5: “It’s Not Just an Accent, It’s More of an Attitude.”

Nothing kills a Boston-set movie like bad Boston accents. Affleck was determined to make sure that his main cast could at least pass as true Massholes.

Welliver: I had an experience several years before for a David Kelley show called The Practice which took place in Boston. I went in to audition. I was playing a character that was from Boston and I worked really hard on the accent and went in and did my first rounds and the director said, “That was great. Yeah, don’t do the accent.” I said, “Well, wait, this show takes place in Boston and this guy is from Boston.” He went, “Yeah, yeah, but you know, we don’t do the accent.” I was kind of, “Well, what’s the fucking point of basing this in Boston? Then put it in Connecticut.”

Affleck: There did kind of get to be a glut of Boston movies, and everybody did a Boston accent. The whole reason Matt and I wanted to do Good Will Hunting was kind of as an acting reel so that we could get jobs as actors. So we wrote parts for characters with Boston accents because we thought that was something that we could do well and that you saw done badly.

Stockard: I think the rule that Ben and I always kind of operated with, was like, “Look, there are people like me and you who are very much from Boston who don’t talk like that.” It’s not some weird thing that someone from Boston doesn’t have a Boston accent. And so if you can’t do it, just don’t do it.

Affleck: Typically people you saw who did it badly would err on the side of doing the Kennedys. You know, the Kennedys kind of had their own weird accent. It was sort of trying to be patrician and they had, and still do, a very distinct way of talking that’s not actually common to most people in Massachusetts, in my experience. But mostly a Boston accent depends on your socioeconomic status, by and large. So there’s a whole range of accents.

Carter: A woman named Ginaya Green, who was a 20-something- year-old, born and raised in Charlestown, let me come and take photos of her bedroom, and her house, and her decor. We did all that kind of stuff. And then she recorded her voice, read some of the pages, so that we shared that with Blake Lively, so she could try to get the accent down. And Blake spent some time with her. And then we put her and her cousin in the movie.

Crockett: [Lively] would go out every night and hang out with Townies. That whole character she did was really kind of based on her own preparation.

Affleck: Rebecca worked just as hard on the accent. I had somebody from Marblehead quote all her dialogue. And she really focused specifically, not only on like, an American accent, but what it sounded like in Marblehead, which doesn’t sound like Charlestown.

Hall: I wouldn’t really say I did a Boston accent. He was quite clear. He said, “She’s slightly different.” Marblehead is a little chi-chi. It’s more general American but with a kind of East Coast, sort of slightly privileged vibe. I was doing that.

Cooper: He got me about five [recorded] voices and one in particular—this one of somebody who had done time—was just so full of character and I just loved it, and so that’s what I glommed onto. It was as simple as that.

Slaine: Owen and I didn’t have to listen to anybody.

Burke: I’ve heard people say, “Oh, we don’t sound like that!” And I’m like, “I don’t think you guys really listen to yourselves. I don’t think you know how you sound.” Actors tell me that that’s one of the toughest ones they have to do. It’s not just an accent, it’s more of an attitude.

Craig: I lived in Somerville for a while in the ’90s. The one thing I miss about Boston is you saw a fistfight every day.

Hamm: I met with Ben and he was like, “You know, I think we’re gonna have plenty of Boston accents in this.” I was like, “You know what, you’re absolutely right.” Once I started meeting all the Federal agents in the [FBI] office, very few of them are actually from Boston. You definitely get more of that in BPD and the local cops. The feds, they get shuffled around all over the country. The guy that I spoke with, who was kind of our head technical adviser from the FBI, was from Nebraska. The only time I attempt it is when I’m basically making fun of Ben, his character, about the Stah Mahket.

Affleck: When this movie came out, the Boston Phoenix review said it had horrible Boston accents. I was only comforted by the thought that no one with a Boston accent has ever actually read the Boston Phoenix. If the Herald said that, I might’ve taken it more personally.

Part 4: “I’m Getting to See Something That Not a Lot of People Get to See.”

The North End, Boston’s Little Italy, is one of the city’s smallest, densest, oldest neighborhoods; the asymmetrical Fenway Park, which fits snugly on a single block, is picturesque but impossibly cramped. The Town stages heists in both places.

Affleck: I certainly didn’t want to set myself up to fail, say yes I could do something, shortchange myself [and] produce a substandard sequence because I didn’t have the time. The money was all on the screen. No above-the-line people got paid any money. It all went to the actual production of the movie.

Stockard: The movie that we thought about was [Michael Mann’s] Heat. And so I think at first we were sort of like, “Oh, how can we not be Heat?” And at some point we said, “Look, embrace Heat. Don’t run away from it.” We love that movie, don’t be afraid of doing things that they did that worked.

Affleck: I’d been in action sequences plenty, so I kind of knew how they worked. I’d been in good ones and bad ones, but I knew that it took time, that they were the result of the assembly of a lot of little pieces.

Alexander Witt (second-unit director): We talked and we said, “Let’s do it as classic as possible.”

Burke: There were the most narrow streets you could find in the North End. I don’t even think they had sidewalks.

Witt: It’s not like New York or Los Angeles where you have wider streets.

Affleck: I had great stunt drivers. They really loved the idea of putting these masked avengers in minivans.

Matheson: We’ve had this official tour [of Boston’s FBI office] and as we’re leaving, I notice a picture across the room, pasted to the wall, of a person in a mask, from the CC TV. And I say, “What’s that?” And they say, “That’s a still of someone robbing a bank.” And I said, “Did they rob the bank in that skeleton mask with the dreadlocks?” They said, “Yeah.” So I became obsessed with that mask. That was the moment where I realized that I could differentiate one bank robbery from another.

I knew that many of these bank robbers had gone to Catholic schools as children and been taught by nuns. I said, “Is there any way in hell that you can imagine that someone would ever rob a bank if they’re from Charlestown dressed as a nun?” And the FBI agent I was meeting with turned to me and said, “You know what, that’s not a bad idea at all.” And that’s where that idea started. I came back and met with Ben, and I was so excited.

I showed Ben the skeleton and Ben said to me, “How can we make it look tougher?” And I said, “Why don’t we put them in tactical gear?” And so that started this riff, this juxtaposition of skeletons and tactical gear. And well, why not nuns and tactical gear? That’s what happened.

Affleck: Those little streets created something visually interesting that you don’t see in many car chases. It very much had a sense of place.

Witt: You don’t want to go, like, Quantum of Solace at the beginning where you really don’t even know where you are, where you shot it. There’s so many shots and so quickly, that at the end, “OK, what happened? Who was in which car?”

Burke: I remember we were all standing around and they were like, “Oh yeah, we’re gonna blow this thing.” There was a van parked there and they fucking blew it up. They blew it up and both sides of the street, all the brick buildings were totally covered in soot. And I was like, “Why are the people who live here letting us do this? Did they know that this was in the plans?”

Affleck: The only other thing I’ll say about the chase sequence, it definitely reminded me of Jimmy Tingle in the ’80s. During the Cold War he had a great joke: “The Russians won’t invade Boston, there’s nowhere to pahk!” I thought, “Yup, there’s a lot of truth to that.” That was our greatest hurdle. Just finding a place to park the trucks.

Staging a chase scene in the North End was difficult, but shooting a robbery inside and around Fenway Park was unprecedented. Pulling off the heist—Doug and his team steal the $3.5 million in cash amassed during a four-game series against the Yankees—without it devolving into a cartoonish homage to the iconic setting took precise coordination.

Stockard: There is this over-the-top sense to these movies. And so, constantly, Ben and I are trying to make it as real as possible. And so yes, they rob Fenway, but it’s not like he’s running across the outfield getting tackled by Tom Brunansky with a bag of money in hand.

Affleck: I made sure that we had enough money to do the Fenway heist sequence in total, which was a lot. And we had a lot of days for a movie that was relatively inexpensive. The way we did that was to make the days inexpensive. That was sort of the trick. It’s something I’ve seen other directors do. David Fincher does an even more exaggerated version of that. He often has a very small crew. Gone Girl we shot a hundred days for a two-hour thriller.

Crockett: The Fenway heist was really just a logistical kind of clusterfuck. How are you gonna figure this out because you want to drive an armored car out of one of our gates?

Stockard: Ben had a good relationship with the Red Sox.

Affleck: The Yawkey Red Sox, I’m sure, would’ve been impossible.

Crockett: As he puts it, you have so many fame chips you can use. So he uses them in that way. I’ll use them because I’m from Boston to get into Fenway. We literally took over Fenway.

Affleck: The Red Sox were really smart and understood how vital and central their organization was and is to the city, and they loved the idea of it. And Major League Baseball was open to it—that was what I was really afraid of. But the Red Sox were definitely in the spirit of, “This is gonna be fun. It’s a fun heist movie.” [Owner] John Henry visited the set. [Chairman] Tom Werner’s a friend of mine. They were excited.

Colin Burch (vice president of marketing and broadcasting, Boston Red Sox): We had filmed a number of movies before at Fenway, starting with Fever Pitch, and we did Ted, and RIPD, and Moneyball. [It was] probably the most intense production that we’ve had at the ballpark—from both an overall action perspective, but also the grandeur of it.

Hamm: We had this 15-day stretch where we had to shoot at Fenway.

Burch: We did it during off days. September 2009.

Hamm: There’s nothing weirder than an empty stadium. Especially when you’re in a park that’s not open to the public. So we had access to all of the underneath [of it], because that’s where we shot a lot of it. It was wild. It definitely felt like, I’m getting to see something that not a lot of people get to see.

Burke: To go sit in the stands with Jeremy Renner in an empty stadium, it was surreal. It kind of had a post-apocalyptic feeling to it. If the world was empty, what would you do? I’d go sit in Fenway and be the only guy there.

Hogan: I had a friend who worked at Fenway Park, who snuck me in while they were shooting that whole sequence. So that’s cool. I kind of got to tiptoe around and watch them shooting from afar without them knowing I was there. Which was nice. When I got there, I went up on the walkway, on the first-base side, looking down. There were 150 people down there working. They’d closed off the street, working on this story that I had cooked up in my bedroom at home.

Warner Bros.

Craig: I was a crime writer already. So if you give somebody a space, all they want to do is figure out how to do a heist in there. I was at that point in my career where every place I walked into I was trying to figure out how to write a robbery in that space. There’s something so tomb-like and archaic about Fenway.

Welliver: We’ve got a couple of great little homages to The Friends of Eddie Coyle when they’re in Fenway: “You live at such and such a street …” That’s completely Alex Rocco talking to the bad guy and he’s saying like, “We have your wife and your children are in the house. Do everything you’re supposed to do, they won’t be harmed.”

Slaine: I worked at Fenway Park when I was a kid, so to go in there and be shooting machine guns was pretty cool, pretty surreal.

Burch: When they’re down in Gate D, where the shoot-out scene was before they exited the ballpark, that was probably the most challenging part of it. Because you’re in a confined space, not a soundstage. And more than anything, just from a noise standpoint, it was kind of unique. Just because the echo in the ballpark. When you’re underneath in the concourse space, you could drop a keg at one end of the ballpark and have it reverberate all the way around.

Slaine: I’m convinced my hearing is still not the same after that film.

Carter: Someone was getting married. And someone had forgotten to tell them that we were downstairs shooting. So all of a sudden, while they’re getting married, they hear gunshots at Fenway. Then they realized that we’re shooting a movie. It was kind of a moment for them.

Affleck: The day that we’re shooting the shoot-out with Jeremy, where he gets killed out in front of the McDonald’s behind Fenway—when you do these stunts with cars, you have to really clean the streets immaculately because these drivers are precision drivers. They’re stopping at an exactly certain point and if they go too far, people’s lives are at stake—it’s a very serious thing. But the machines they use to clean the streets are very loud and we were cleaning the streets at like 7 in the morning and out of this apartment building comes Jonathan Papelbon. He’s like, “What the fuck are you doing? You woke me up.”

Carter: That scene at the end, where you see [Jem] running across the street trying to get away from the cops, and the cars, obviously those are stunt drivers, they’re stopping really quick. The first or second take that he did, Jeremy wanted to do it on his own. And everyone was like, “Ah, you can’t, really. It’s kind of like a safety thing. What if something happens to you?” But he’s so agile, and he’s so athletic, and he has no fear, just absolutely no fear. And this was toward the end of the shoot. He’s just great. We all sat there, and he did it.

Welliver: So, when [Jem] gets killed at Fenway, when the cops dump him and [there’s] that brilliant thing of him reaching down and taking a sip of the soda behind the mailbox, it was a little bit of, “Top of the world, ma!” It’s heartbreaking. He humanized that character in that moment. He was definitely a bad guy and was going to take as many people with him as he could, but you still kind of went, “You know what, this is a kid that came along, and in a different environment he would’ve been a different person but he is a product of all of this dysfunction and horror that he’s grown up in.” It’s brilliant. It’s fucking brilliant.

Slaine: I was hanging with Gronkowski, and he’s like, “Dude.” He’s like, “The Town, is there going to be a sequel?” He was like, “You gotta do it, you gotta be in the sequel.” I said, “Dude, I died at the end.”

Part 5: “You Get to Root for the Bad Guys. What’s Better Than That?”

The Town was initially supposed to end with Doug paying for his sins with his life. But instead, Affleck went with something more bittersweet. After managing to evade a manhunt and escape to Florida, his character says goodbye to Claire via a letter.

Craig: We went into a bit of a quandary about the ending. I watched a screening with a different ending and it hadn’t been testing well. There was one of my endings and Ben wrote a couple endings, and that’s Ben’s ending that they used. I had a darker ending in it, like a real ’70s ending, where Doug dies. I was still in the ’70s mindset of, “Oh that’s how you end one of these movies. He gets punished.” I just still really thought that way.

Stockard: Do we want to punish this person or do we not? Or do we want to give him a chance to live and a better life?

Craig: I hadn’t really processed the new ending. And I hadn’t seen it with the new one tacked on. When I saw it, I thought, “It’s fine.” I wound up learning a lot from how Ben did that. Honestly, people just wouldn’t have liked the movie [with my ending]. They like walking out with a little bit of hope. It at least had that upswing.

Hall: It felt like cinema in the classic sense.

Slaine: I’ve seen other cuts of the ending, like the one they put out, the extended version. I liked the way it was released, man. And I’ll tell you why: Nobody was rooting for Jon Hamm and the cops. That’s what makes it great. It’s an action movie where you get to root for the bad guys. What’s better than that?

Warner Bros.

Hogan: I went in to go see it in a screening room in Manhattan like two months before it came out. Walking in I was feeling kind of glib. I’m like, “You know what, if it’s terrible, I’ll get a great story out of it.” I sit down and I watch it, and it was really bewildering. Because along with watching the movie, I was working hard to process it. I wrote the book, then I went away for a while, then I worked on the script for a year, then I went away for a while, then other people wrote the script.

So I leave the movie theater and I’m really kind of numb, trying to figure it out. I walked the city for something like two, three hours, and by the end of it, I realized two things: The first thing was, I really like the movie and I can’t wait for it to come out. The second thing was, I realized what a fool I was to think like, “Oh, if it’s bad I’ll have a story.” I realized that I would’ve been crushed if that movie was bad. So I was thrilled. And I still am.

Hamm: It was an ambitious shoot and it was pulled off without a hitch. And to that end, it’s 100 percent on Ben. He was the leader that he is.

Burch: We did one of the premieres at Fenway. We had this huge screen over the third base dugout.

Cooper: It was kind of this crisp evening. And we saw the film for the first time and I must say: I was across the aisle and up two or three rows from Jeremy, and I don’t know if I’m letting the cat out of the bag, but I think he was thrilled watching that film.

Welliver: When we were doing The Town is when he was up for the role of Hawkeye. He was kind of hemming and hawing a little bit and I said, “Look, unless they make you wear the fucking purple outfit and the mask, you gotta do this.” He went, “I know.”

Cooper: He’s had a wonderful career, but [The Town] was a big shot in the arm for him.

Hall: I remember going to the premiere and a group of Charlestowners were there and they all said to me, “You ever come back to Boston, we’ll get you a car. You can come over to my house for dinner.” It was just short of, “If you need protection, we’re here for you.” It was incredible.

Funny enough, I have shot in Boston twice since then. And it is a bit like visiting royalty there, for me, in a way that I don’t get in any other town or city in the world. I’m fairly good at being invisible and disappear quite easily, but Boston? Forget it.

The movie opened on September 17, 2010, to overwhelmingly positive reviews and eventually grossed $154 million at the worldwide box office. For his turn as Jem, Renner was nominated for the Best Supporting Actor Oscar, though he lost out to Christian Bale, who played the troubled brother of boxer Micky Ward in yet another movie set in Massachusetts: The Fighter.

As for Affleck, the success of The Town helped advance his career as a director. And for better or worse, it was also a hit that—in addition to tax incentives—helped temporarily cement Massachusetts as Hollywood East. There have been dozens of films and television shows filmed in the Bay State over the last decade, but by the time the 2010s came to a close, the popularity of the “No R” genre had faded. After all, there are only so many Massachusetts-set crime stories about Irish American antiheroes that you can tell. Eventually, homogenization came for those tales, too.

Crockett: Gone Baby Gone, which I did with him, was a relatively small movie. And was critically acclaimed. But how many people, speaking frankly, want to see a movie about a child murderer? Or a child abduction? It’s a hard movie to watch. [The Town] is not just entertainment and popcorn. However, everybody will want to go see it. It has a broad appeal. If you say it’s a bank heist movie, people are like, “I’ll see that.” I think it was a great step. It took him to the next level because it made him a filmmaker who also had box office appeal.

Hall: He’s just a very good storyteller. He knows how to get a story from one place to another and connect all the dots in between so that you are in it and immersed in it and believe it and it’s thrilling and it’s really entertaining, as well as being serious. He has that capacity, and I think that makes him a classic American filmmaker.

Welliver: I still think that The Town and Gone Baby Gone, that’s the bar. He set the bar with those films—you [must] reach a modicum of the depth and the artistry of those films if you’re going to do a Boston film. Those are the blueprints, that’s the template.

Affleck: I’m glad to have worked on movies that are part of that tradition.

Hogan: I was playing on a softball team, and this friend, he works for one of the prisons here and he was walking by someone’s desk and they had a picture of Ben Affleck on her screen saver. And he’s like, “Where’s that from?” And she’s like, “Oh, he was here. They were shooting a scene. He wanted to tour the prison and see it.” And the guy said, “Oh, the guy who wrote the book that that movie’s based on is on my softball team.” And she said, “Dennis Lehane is on your softball team?” And that’s when I was like, “It’s a small circle here.”

Stockard: It’s a little weird being a piece of that, as somebody who wrote two of those movies.

Affleck: There tend to be trends and people feel like at first it’s fresh, and then it’s kind of something they like, and then it becomes something that people get tired of. And that’s just sort of the natural progression.

Hogan: I think we’ve played out the Irish Boston gangster thing. There’s a lot of different stories to tell. I keep waiting for someone of color, anyone who’s not like me, this sort of Irish American crime writer, to figure it out and write another great Boston crime movie that doesn’t look like all the ones we’ve seen. I think it’s ripe for the picking.

Affleck: I was very self-conscious about being limited to being the Boston guy. I was like, “I’m not gonna do another movie in Boston. Nobody’s gonna hire me to do anything except Boston.”

Stockard: I said, “You can do Boston again, but let’s get out of there for a while.”

Affleck: Which is why I was like, “Great. Iran. I’m gonna do a movie about Iran.”

These interviews have been condensed and edited for clarity.

An earlier version of this piece misspelled Roslindale.