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Paul Asay

Movie Review

The Land of Opportunity.

That’s what America is, they say. In America, you can be anything we want. You can overcome your upbringing, overwhelm your circumstances and do great and glorious things. We have the opportunity—granted us by our forefathers, documented in parchment and brick and stone. Whole cities—New York, Philadelphia and Boston—were built as testaments to this promise—beacons from a New World.

Fast-forward 200-plus years. Boston is a maze of narrow streets and brick buildings, a labyrinth of time. And in its innermost recesses—in such communities as Charlestown—some folks have given up trying to find their way through. A few square miles becomes a whole world, where sons do as their fathers did, who do as their fathers did before.

And if those fathers and grandfathers happened to be bank robbers?

Doug MacRay could’ve been a professional hockey player. He had the talent, but he squandered his chance and went back to Charlestown, and there he stayed. His father’s in prison, his mother disappeared when Doug was just 6. But still he hangs on to his makeshift family: his best friend, James—a prison-time vet with a murder rap to his name; James’ sister, Krista, who cares for a daughter who may (or may not) be Doug’s; layabouts Gloansy and Desmond. They drink together, have cookouts together and, when opportunity strikes, the men rob banks together.

Boston, it seems, is still a land of opportunity—just not as our forefathers intended.

Then, during a job, James takes a hostage, Claire. They release her unharmed, but the gang’s haunted by the fear that she might’ve seen something. So Doug spies on her, works his way close to her. And in a moment of weakness, he asks her out. The two begin dating. And as Claire and Doug grow closer, Doug begins to think about a different kind of opportunity—the chance to find a different path, to live a different life.

People talk all the time about changing their lives and never do it, he tells Claire. “I’m gonna change mine.”

But the town doesn’t relinquish its own so easily. A new “job” calls, and even though Doug doesn’t want to participate, the gang won’t take no for an answer. And the FBI is closing in, eager to reunite Doug with his father. The truth of Doug’s black past and present lingers in the air like a malignant spirit between he and Claire, threatening to squelch opportunity for good.

[Note: The following sections contain spoilers.]

Positive Elements

Doug is obviously and deeply flawed, but he does have something of a moral compass—as wildly erratic as it sometimes is. He doesn’t drink (his friends make fun of him for it) and doesn’t seem to do drugs (unlike his sometime girlfriend, Krista). He wants to leave the town and all its moral pitfalls behind. And yet he also feels the pull to stay true to his lifelong friends.

The decision is made harder by the extraordinary loyalty his friends have shown him. James, for instance, spent nine years in prison “protecting” Doug—killing someone who had planned to kill the budding hockey star. It was a flagrantly flawed strategy, but within the lawless street ethos James and Doug were raised in, this passes as a form of near chivalry.

Spiritual Elements

Doug and his pals seem to exhibit an offhand sort of faith: We see characters wearing crosses around their necks, and one tells his cohorts to “say your prayers” before they go in and rob a bank—when all of them, incidentally, are dressed as nuns. Both Doug and his father tell others, “I’ll see you again, this side or the other.”

An FBI agent says they’ll never get full-time surveillance on the suspected bank robbers “unless one of these idiots converts to Islam.” A man tells a joke that, in a roundabout way, references God being with us in times of need.

Sexual Content

Doug and Krista appear to have a casual, largely sexual relationship. After a night at the bar, both head to his apartment and have sex. Both are clothed; she straddles him. There are sexual motions and sounds. Krista showcases her breasts and flirts with other men, including an FBI agent. “You gotta chase the rabbit if you want the tail,” she tells him. “My mom taught me that.”

But Doug apparently longs for a deeper relationship, and he seems to find that with Claire. Not that deepness replaces sex for them. After a few dates, they migrate to the bedroom. Naked, Doug lies on top of Claire. (The camera hints at what they’re doing, but doesn’t show the explicit things it showed with Doug and Krista.)

A bare breast gets screen time at a strip club. Crude references are made to male and female sexual organs. The script includes a few crude double entendres.

Violent Content

“All who draw the sword will die by the sword.” So said Jesus in Matthew 26:52, and so the film industry often preaches. While one can take issue with Hollywood-style morality, moviemakers are pretty consistent when it comes to the idea of violence begetting violence. And The Town, with one important exception, doesn’t allow its violent malfeasants to live.

James is the gang’s most violent soul. We see him club a bank manager with the butt of a gun and pummel a hoodlum with a baseball bat before shooting him twice in the leg (just for fun, seemingly). He asks Doug whether they should rub out Claire as a precaution. Whenever the gang gets into a bind, it’s presumably James (we can’t be sure since they’re often wearing masks) who pulls out his guns and starts shooting, often injuring or even killing cops and security guards.

Perhaps it shouldn’t come as a surprise that it’s James who suffers the most lingering death, gunned down in the street by police, getting shot first in the leg (we see a spray of blood), then the face.

Other lawbreakers are killed in shootouts or traffic accidents—and none of these deaths are very pretty. We hear that Doug’s father was sentenced to several life sentences for killing two security guards. And we see pictures of them lying dead, their heads bloodied and disfigured. Later we hear that someone “split him up his back” in jail.

Doug and James scuffle. People are beaten. Audiences see prolonged shootout sequences, and a car chase features tons of smashed-up vehicles and, presumably, lots of offscreen injuries. Cars are blown up. We hear about how a crime boss chemically castrated a lackey. And Doug later castrates someone by firing a gun into his crotch. Somebody threatens to neuter Doug, saying he already did so to Doug’s father—driving Doug’s mother to suicide. “If there’s a heaven, son, she ain’t in it,” the man tells Doug.

Crude or Profane Language

The f-word tally exceeds 150. There are about 15 s-words. Characters say “a‑‑,” “b‑‑ch, ” “b‑‑tard” and “h‑‑‑.” There are a half-dozen exclamations of “g‑‑d‑‑n.” Jesus’ name is abused that many times too.

Drug and Alcohol Content

Krista spends most of her screen time strung out on cocaine and the painkiller OxyContin. She also drinks quite a bit, as do others—many shown frequently with a bottle of beer or a glass of booze. Doug tells James that all he seems to care about is “coke and Xbox.” Doug attends what appears to be an Alcoholics Anonymous meeting. A few people smoke.

Other Negative Elements

Claire withholds information from authorities to protect herself, then tries to protect Doug from the FBI by delivering a message in code to him over the phone. Doug treats Krista harshly, slamming the door in her face at one point.


In the heart of the Great Depression, gangsters were gold. The press made them stars, movie reels made them immortal. Hostages would later say what fun they had hanging out with John Dillinger, what a hoot it was to chat with Bonnie and Clyde. For much of America, they were our charming avatars—folks who busted through the dismal economy and societal norms and lived large—the way so many longed to.

Our culture was not devoid of morals back then. I’d like to think we embraced these gangsters more in spite of their lawbreaking than because of it. Many hoped their heroic hooligan favorites would manage to keep eluding law enforcement … but fantasized that they’d settle down after one big climactic heist, to live in luxury down south somewhere. They’d marry and have children and join the Rotary Club, you bet they would! The bad boy would turn good.

In The Town we have such a bad boy: Doug, our handsome, conflicted antihero, escapes the clutches of the FBI and settles down somewhere in Florida. He leaves a satchel of money behind for Claire, to use as she wishes. She, we surmise, spends the money on a local hockey rink: A plaque along its side says it was an anonymous donation, made in the name of Doug’s mother.

“No matter how much you change,” Doug writes to Claire, “You gotta pay the price for what you’ve done.”

We hear this in voiceover mode, as we look at Doug who’s looking out at the sea, looking like he’s literally a thousand or so miles away from “paying the price” for anything.

I was supposed to feel good about this finale, I guess. But these voices kept popping up in my brain, spoiling the movie’s happy ending:

_It’s nice of him not to keep the money, isn’t it? Sure, except he didn’t exactly give it back, and neither did Claire. And if Claire stole my wallet and tossed it in a Salvation Army kettle, it’d still be stealing, right? And I’d still want it back and her thrown in jail.

But Doug wasn’t as bad or as bloodthirsty as James, was he? He deserves a bit of leniency, maybe. Well, now I’m not so sure. He did break into someone’s apartment and beat the living daylights out of, essentially, a stranger. Oh, yeah, and he executed two other people in cold blood in their own shop.

But they were the baddies! They deserved what they got!_

And therein lies the biggest problem with such films as these. We’re manipulated to root for one thief and killer to “take care of” another thief and killer. One is, naturally, handsome and conflicted. The other is, naturally, misshapen and one-dimensional. This used to be how justice was too often meted out. Folks we liked got a pass. Folks who were a bit different—maybe folks with a lazy eye or crazy hair or a penchant for antisocial behavior—didn’t. Society often suffered at the fickle whims of we the people.

It was because of that that we now live in a land of laws and regulations. They’re imperfect, yes. But faith gave them life, our forefathers confirmed them and time has refined them. These are the same laws that provide the underpinnings for this great Land of Opportunity that so many revere. These are the laws that The Town—in its quite moving, extraordinarily foul way—flouts.

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Paul Asay
Paul Asay

Paul Asay has been part of the Plugged In staff since 2007, watching and reviewing roughly 15 quintillion movies and television shows. He’s written for a number of other publications, too, including Time, The Washington Post and Christianity Today. The author of several books, Paul loves to find spirituality in unexpected places, including popular entertainment, and he loves all things superhero. His vices include James Bond films, Mountain Dew and terrible B-grade movies. He’s married, has two children and a neurotic dog, runs marathons on occasion and hopes to someday own his own tuxedo. Feel free to follow him on Twitter @AsayPaul.