Bobby O’Grady (Denis Leary) is an Irish-American hood from Boston. We are introduced to him as he and his buddy Mouse (Ian Hart) are racing a couple of stolen cars back to a fence (Lenny Clarke) where they’ll collect some cash for their trouble. Later on they meet up with Digger (John Diehl) a studdering cabbie and Bobby’s cousin Seamus (Jason Barry) who is from Ireland. They drink, snort coke and as the night wears on they sit in Bobby’s house and tell stories, vote on their famous hot actresses and just have a good time. Bobby and his cohorts seem to live with no real hold on the future and when you live outside the law like they do, things can often go bad at any moment.
Bobby hears that his old friend Teddy (Billy Crudup) who had been in prison is now free and has shown up at their favorite bar. When Bobby sees Teddy, he appears to be very jittery and something about him causes Bobby to feel weary. As the guys welcome Teddy back and reminisce about the old days, Bobby’s boss Jackie O’Hara (Colm Meaney) stops by their table. He jokes around and Teddy assures him after he makes it known he was questioned by the Feds, he said nothing about Jackie or his criminal enterprise. Jackie seems content with Teddy’s story and leaves. Suddenly, one of O’Hara’s soldiers Shang (Greg Dulli) shoots Teddy point blank, leaving Bobby and the others in shock. They all know they have to keep quiet about this because Jackie is their bread and butter and has no qualms about seeking reprisals on snitches. Soon a local cop named Hanlon (Martin Sheen) appears and begins putting pressure on the crew but Bobby and his friends won’t budge. It’s a local thing, and they aren’t going to squeal on one of their own.
Bobby also has an on and off again relationship going with a local waitress named Katy (Famke Jannsen) who is a bit of a wildcat, but he does his best to treat her right, until one night he sees her flirting at the bar, which makes him seek revenge. He makes his own move on a woman (Jeanne Tripplehorn), and tries to get her number until Katy drunkenly confronts them in the street scaring the woman away, after which Mouse and the boys drive up in Digger’s cab and ruin his chances completely.
When none other than Jackie begins dating Katy, he and Bobby’s boss/soldier relationship begins to go sour fast. A major devastation occurs when Bobby’s cousin Seamus turns up dead on the street one night. When Bobby sees the ongoing trauma his life as a criminal is having on his family and community he starts to rethink what he really wants in life. He must then decide to either stay under Jackie’s thumb or make some kind of a positive change.
One of the films most suspenseful sequences occurs when Bobby and his friends see a black man walking through their neighborhood. This causes another of Bobby’s pals, “Red” (Noah Emmerich) to go into ranting racist mode. Tired of listening to his tough guy B.S., Bobby orders Digger to turn the car around and they kidnap the poor guy at gunpoint and bring him to a secluded place. Bobby looks like he is going to kill the man but thankfully is only putting on a show to try to make a point to the loud talking Red, although not a very subtle one.
What Monument Ave. does exceptionally well is portray the Boston Irish-American neighborhood characters in a true light. Often these kinds of hoodlum/gangster films (of which there has been many over the past 20 years), and especially the ones set in Boston, get a bit hokey in regards to how the people act and talk. The screenplay, which was co-written by Denis Leary (who grew up in Central Massachusetts and Boston) was excellent in how it showed the authentic personalities of the area. You can tell he has met these kinds of people throughout his life. It’s all about the little moments that seemed to hit it just right with Bobby and the boys and how they interact. Added to that, Director Ted Demme did a fantastic job establishing the atmosphere and casting the perfect people that Bobby lives with and around making it one of the most believable films of its kind. Fans of other Boston based crime films such as The Friends of Eddie Coyle, The Departed and The Town will find alot of similar themes going on in this gem.
Director Ted Demme went on to make another great crime film Blow (2001) starring Johnny Depp as Boston native George Jung, who was one of the original cocaine kingpins. Sadly it was Demme’s final movie. He passed away after its release. It was a true swan song that showed how much promise he had as a newer filmmaker.
