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Townies And Toonies
When we meet the character of Doug MacRay, he and his crew are in a van outside the Cambridge Merchant Bank, seconds away from their next robbery. In Affleck's words, Doug is "banging against the walls of his own life, still doing the stuff he knows is bad for him but unable to change.”

Affleck continues, "He had a shot at a different future—he had a chance to play pro hockey—but he self-destructed. He got addicted to drugs and spun out, so instead of getting out, he came back and, in spite of himself, ended up even deeper in it. That's where we find him. He's cleaned up a bit, in terms of getting sober, and he wants to leave, but he can't escape his circumstances.”

"That's what was most intriguing about this guy,” Stockard asserts. "He is at a point in his life where he realizes if he doesn't leave, he's never going to change. It's not just that he doesn't want to go to prison or, worse, get killed, which is what will inevitably happen if he stays in Charlestown and continues to do this sort of work. What he wants more than anything is to be a different person.”

"Part of where he is in his life is a function of how and where he grew up,” Affleck relates. "His mother left; his father was in this life; and Doug wound up doing the same thing as the friends he grew up with. It doesn't excuse it, but hopefully you see the shades of gray in the reasons he ended up where he is. It's not just cut-and-dried.”

"Ben really understood Doug's psychological and emotional journey,” King says, "so when he said he was interested in playing the role, we knew there was no one better,” says King. "I was blown away, not only by how Ben depicted the arc of the character but by the intensity of his performance.”

The arc of Doug's life contrasts sharply with that of Jem, his closest friend and a kind of brother-in-arms, albeit on the wrong side of the law. Unlike Doug, Jem is resigned to the life he was essentially born to and has no compunctions about his criminal pursuits.

Jeremy Renner observes, "Given their upbringing, Jem and Doug had to lean on each other throughout their lives, so they are definitely more like brothers than friends. But now Doug is veering away from the only life Jem has ever known and Jem is trying to reel him back in, to knock some sense into him, as if to say, ‘We're bank robbers. That's what we do; that's all we are.' The conflict between them lies within that.”

"Doug and Jem have a complicated back story,” Affleck comments. "They've been best friends since they were kids, but they have become very different people…people who would not be friends if they met today. However, because they have this shared history of loyalty and love they are bound to each other, and that puts a lot of pressure on Doug. Jem is always on the verge of being out of control, and Doug is the only one who has been able to make sure he doesn't go too far.”

Renner agrees that Jem is "a wildcard,” noting that his character's propensity for violence added to the challenge of making him multidimensional. "He is not any one thing. He's flawed—maybe more flawed than others, but there are moments when you see another side,” the actor contends. "It was important to me that Jem be a fully realized human being and not just some gun-toting thug. I understood that he could be a scary guy, but I also wanted to bring a sense of humor and heart to him.”

According to Iwanyk, Renner succeeded. "Jeremy was a revelation. He transformed Jem from being just a crazy menace to someone I was emotionally invested in. My heart broke for him, which is something I didn't anticipate when I first read the script.”

"Jeremy captured the dichotomy of this guy who does things that might seem unforgivable, but, by the same token, you still like him,” Affleck affirms. "Jem is obviously damaged, but you can see why he is who he is because of what Jeremy brought to the role. He is a terrific actor and such a sweet guy, and that humanity bleeds through the pores of his performance.”

Renner says that Affleck—both as a director and as a castmate—made portraying the enduring friendship between Jem and Doug a natural. "I felt like I was working with one of my best friends. Ben empowered me to do whatever I thought was right, and if it worked, he got so excited. He set an amazing tone and made everyone feel relaxed and comfortable. It was great.”

The subtle rift that had begun between Doug and Jem is amplified when, during the Cambridge Merchant Bank job, Jem brutally beats the assistant bank manager and then, in a sudden and desperate move, takes the bank manager, Claire Keesey, hostage.

Though the gang quickly releases her, Jem, in particular, gets nervous when they discover that Claire lives in Charlestown, within blocks of them. What if she saw or heard something that could connect them to the robbery? Jem would rather not wait to find out, but, knowing what that might mean, Doug steps in. Affleck details, "In an effort to calm everybody down, Doug says he'll deal with it. He starts following Claire around, which leads to an unexpected encounter. And that sets in motion a series of events that will change his life.”

In fact, another kind of "change” is the innocuous reason they meet, when Claire approaches Doug at the Laundromat asking if he has any spare quarters for the machine. Claire has no idea who Doug really is or that they already have a connection. Ironically, it's that connection—the bank robbery and her being taken hostage—which becomes the catalyst for their romance.

Rebecca Hall explains, "It's that thing that happens when relationships are fostered in extreme circumstances: the bonds are much closer. The fact that Claire meets Doug when she is crying and having a bit of a meltdown leads to an immediate spark between them—not necessarily because of any natural chemistry they have, but because she needs someone in that moment and then there he is, this stranger, smiling at her and making her laugh. In other circumstances maybe she wouldn't have gone out with him, but she's open and vulnerable and he appears slightly like a knight in shining armor.”

Affleck says he cast Hall as Claire not only because "she is beautiful and incredibly talented, but she has this way about her that feels real. That kind of honesty and normalcy was especially important for this role. You believe she is somebody who could work in a bank. She seems like she could be someone who just moved into this neighborhood.”

Hall remarks, "I thought it was fascinating that this sort of, for lack of a better word, ‘yuppie' kind of woman—what the local Townies call a ‘Toonie'—is making her home there and going about her life even after what happens to her. I thought there had to be something strong and sassy about her, that she refuses to be victimized. It made her interesting to play.”

As the connection between Doug and Claire deepens, Affleck says, "She comes to represent the way in which he can finally change…the version of his life that could be different from what he's known.”

The more Doug sees alternatives in his life, the greater a threat he is to his crew, as well as to Jem's sister, Krista, though not for the same reasons. Blake Lively, who plays the role, offers, "All Krista wants is for Doug to love her and take her away from there. She's grown up around these tough guys who are doing everything wrong, but they were her only role models. Now she's a single mom who does what she has to do to get by.”

Lively adds that Krista's mix of street smarts and fragility was what drew her to the role. "She has layers of darkness and vulnerability and toughness and desperation. Krista could easily appear to be not very redeemable

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