South Bostoners Bobby O'Grady (Leary) and Mouse Murphy (Ian Hart: Enemy of the State, The Butcher Boy) are small-time hoods in the employ of Irish mob boss Jackie O'Hara (Colm Meaney: Mystery, Alaska, This Is My Father). Their crimes run mostly to stealing "yuppie" cars and burglarizing "yuppie" apartments, but they're not above petty vandalism, like wandering the quiet residential streets of Boston at night and kicking all the cars to set off their alarms. For fun, Bobby and Mouse hang out with Bobby's cousin Seamus (Jason Barry: Titanic), over from Dublin, and snort coke and drink beer while appraising the attributes of Hollywood actresses ("I don't like fake tits," Bobby announces) and debating heady topics like, Which sport is more boring, soccer or baseball?

They're losers, and they know it. Bobby, 35 if he's a day, still lives with his mother, and that doesn't seem likely to change. He's a slave to the laws of the street, to loyalties that have him irrevocably tied to Jackie. Or so it seems. When another cousin of Bobby's, Teddy Timmons (Billy Crudup), is murdered after rumors fly that Teddy ratted out Jackie to the cops, Bobby finds himself questioning his chosen life. For all that Monument Avenue's story is about crime and criminals, this is a fairly low-key drama highlighted by only a few outbursts of violence. The conflict is internal: Is Bobby capable of having a change of heart?

Bobby himself, though, is a powder keg, and just as Leary's reputation for frenzy as a comic serves him well in lighter roles, his unrepentant taste for danger -- see his unapologetic rants about the pleasures of smoking, for instance -- have a way of seeping into Bobby, making his performance intensely believable. Bobby, for example, is the kind of guy who insists "I ain't no racist" while simultaneously complaining about everyone not white and preferably of Irish descent. One evening, Bobby and friends are driving around when they spot a young black man walking alone through the streets of their Irish neighborhood. When his friends start grumbling about the city going to hell, Bobby pulls a gun and makes them stop the car and snatch the black kid off the streets. In the confrontation that follows, we're not sure until the very end whom Bobby is trying to terrorize, the frightened black kid or his own now-frightened friends -- we're not sure how Bobby's weariness with the violence and uncertainty of his own life is going to manifest itself. This scene -- in fact, the entire role of Bobby -- is an actor's dream, and Leary practically inhabits him.

In the end, Bobby's dilemma comes down to family. Which family will he choose: the one he was born into or his family of the streets? In many ways, they're one and the same -- director Ted Demme intercuts his scenes with photos of Bobby and Mouse and Teddy and other characters as children, playing together, their arms thrown around one another. At Teddy's funeral, Bobby's mother laments "all these mothers" that have had to bury sons murdered by mob justice. These sons grew up together, and they're dying together -- another tragedy is ultimately what pushes Bobby to finally make a decision. But can he live a life without this family?

Monument Avenue doesn't offer Bobby any easy ways out, and it won't leave you feeling warm and cozy. I wish there were more films like this.