Bobby O'Grady (Denis Leary) still lives with his mother in a musty apartment in a working-class Boston area. He still hangs with his childhood buddies, and they all work within a small crime syndicate run by another old pal named Jackie O. (Colm Meaney). These small-time Irish-American hoods steal cars and work insurance scams, and in between they hit the drugs and share some laughs. The early passages of Monument Ave.,where we get to meet these guys and see them in their daily grind, have a real life to them. Director Ted Demme and writer Mike Armstrong aim a clear and incisive eye at establishing a comfortable, natural rapport among these lifelong pals. This is material at which Leary particularly excels-the angry wiseguy airs of exasperation he wears for his stand-up act make for a comfortably droll fit in the forum of old buds shootin' the breeze. Surprisingly, Leary also shows a relaxed depth of feeling when the story turns to more serious matters.
Too bad for Leary and the other fine actors that as soon as the script turns serious, the film slows to a languid crawl, and ends up as a slight retread of all-too-familiar elements. In an instant, Monument Ave. shifts into self-important melodrama, as Jackie O. turns things violent by weeding out the disloyally talkative elements from within his crime ring. This leaves the film alone with an achingly simple conflict. Bobby watches as his friends are taken down in the name of business, and he must decide what to do about it, whether to sit by and do nothing, run away from it all, or take action.
The difficulty of this choice is communicated chiefly through the inclusion of many uneventful moments of Bobby quietly reflecting, moments that serve to make the film's short 90-minute running time feel considerably longer. The problem is that Mike Armstrong's script isn't quite filled in with enough character details or relationships to give Bobby's yearnful looks much of a psychological context. The rich density of the early scenes falls away to make room for this bare-bones story rehashed from past criminal psychodramas, where the crimes inevitably eat away at the criminal's soul. But there are scenes and transitions missing between key moments (one, where Bobby viciously puts a black man through hell to show up a friend, rings particularly false), and so the bittersweet edge that rounds off the film comes across as artificially sweet, and not all that convincingly bitter.
The actors do a valiant job in trying to elevate this material to something more substantial than it is. In addition to Leary's strong work, Ian Hart, Jason Barry and John Diehl are all strong as Bobby's ranging-in-intelligence friends. Jeanne Tripplehorn and Billy Crudup make sizeable impressions in small roles, as a likeably wary yuppie courted by Leary and a jittery, drug-addled member of the gang. But, finally, the slight material overwhelms the individually stong work. Colm Meaney tries to downplay his broad, underwritten role, with limited results, while Martin Sheen just plays his stereotyped role as written, as a tough Irish cop who blurts out most every cop clich in the book. This whole enterprise has been played out many times before, but for an especially similar account that tells almost exactly the same story of imploding Irish-American hoods, with a fuller script and richer psychological stakes, skip Monument Ave. and see State of Grace.