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It’s a just a typical night for aging Boston street kid Bobby O’Grady (Denis Leary), his pal Mouse (Ian Hart), and his fresh-from-Dublin cousin Seamus (Jason Barry). They steal a car, watch guys at the local bar compete to see who can keep a lighted cigarette on his bare arm the longest, and set off the alarms of cars that belong to the yuppies who have infiltrated their blue-collar neighborhood. Then they go home, snort some coke, talk about which female celebrities they find most desirable, and freeze-frame videos at the precise moment that allows a glimpse of famous actresses’ breasts. “I love tits,” announces Bobby.

Coming from the director of Beautiful Girls, this is not a promising introduction. Ted Demme’s previous film featured lots of attractive young performers, but its insights into the alleged psychic chasm between men and women might as well have been cribbed from Erma Bombeck and Jay Leno. (At one point in the movie, Rosie O’Donnell even launches into a stand-up routine.) There are fewer beautiful girls in Demme’s new Monument Ave., but that’s just because the movie is exclusively concerned with what it means to be a man. And in a rough Irish-American neighborhood, that’s a topic of even greater import than Michelle Pfeiffer’s bosom.

Monument Ave. is set in Charlestown, an isolated Boston district whose local significance peaked with the Battle of Bunker Hill. (The monument to that clash, of course, provides the name of the neighborhood’s main drag.) As clannish as the city’s more notorious ethnic enclaves, Charlestown is known for stolen cars and unsolved murders. Mike Armstrong’s script imagines that both are the responsibility of Jackie O’Hara (Irish actor Colm Meaney, in a switch from his usual film role as a sweet-natured bumbler). Jackie O, as he’s called, works the neighborhood more like an alderman than a crime boss, taking care of widows and orphans. Since he’s quick to exterminate anyone he thinks may squeal to the cops, however, Jackie is actually responsible for many of the grieving relatives to whom he tends. Early in the film, in fact, Bobby’s boyhood friend Teddy (Billy Crudup) turns up at the bar, fresh from prison and adamant that he didn’t rat on Jackie in exchange for early release. Within minutes, he’s dead, and Bobby and his friends follow the usual script: They all tell crusading cop Hanlon (Martin Sheen, earnest as ever) that they were in the men’s room and didn’t see a thing.

Bobby works for Jackie, who controls him through his gambling debts, but he’s a bit of a rebel. His most insubordinate activity, however, is strictly clandestine: He’s sleeping with Jackie’s girlfriend, Katy (Famke Janssen, who debuted as a Bond girl but has since been making the rounds of such low-budget American films as City of Industry and Rounders). It’s with Katy that Bobby first shows glimmers of the nobility on which the film’s plot turns: Late one night she shows up at his house, drunk and ready for sex, but Bobby instead encourages her to fall asleep, gently covering her with an afghan.

This quiet scene makes its point in part because Leary (once he gets past the rote boys-will-be-pigs patter of the opening scenes) and Janssen are among the film’s most convincing performers. Demme and Armstrong can’t leave Bobby’s best instincts alone, however. They showcase them again in a sequence in which a few of Bobby’s friends terrorize an African-American college student who finds himself in Charlestown after getting off at the wrong subway stop. (This is geographically unlikely, but never mind.) Bobby finally does the right thing, but only after cruelly toying with the outsider—and the audience, which is really the point. In trying to keep the viewer guessing about Bobby’s character, the scene undermines the film’s central strength, its deadpan naturalism.

Ultimately, things go too far wrong in the neighborhood, and Bobby is forced to take decisive action. The resulting denouement is glib, but not so tidy as to entirely sanitize the film’s believably messy milieu. Armstrong (who wrote another Leary vehicle, Two If by Sea) went to college across the river from Charlestown, but Leary used to live in the neighborhood, and his commitment to getting it right is palpable. More accurately than the kindred Good Will Hunting, Monument Ave. captures the slow dissolution of working-class solidarity in a neighborhood whose primary nemesis is an invisible one: cheap rents.

It’s this sense of place that largely triumphs over the script’s gangster-flick clichés. Demme shows his skill by establishing the neighborhood not with locations but with faces. Using short takes and jump cuts, the director creates an intimacy that’s sustained not only by the principals—Meaney and Sheen are the only ones who seem a little incongruous—but also by such minor players as John Diehl (as a cab-driver accomplice), Noah Emmerich (as one of Bobby’s chums), Marilyn Murphy Meardon (as Bobby’s mother), Afghan Whig Greg Dulli (who also sings the end-credits theme), and Jeanne Tripplehorn (as a yuppie who’s charmed by Bobby for precisely as long as it takes her to realize that he’s one of the townies who regularly harass her). Monument Ave.’s story never becomes entirely credible, but the fluidity of its ensemble cast offers considerable compensation.CP