This is a meaty, engrossing crime picture, right in Martin Scorsese’s wheelhouse. Jack Nicholson is a Boston crime boss who has a quasi-adopted son/mole in the Boston PD (Matt Damon). In that same department, a small unit (headed up by Martin Sheen and Mark Wahlberg) is set up to get Nicholson, and they recruit a police academy trainee (Leonardo DiCaprio) who has one leg in the tough streets of Southie (his dad’s side) and another in the upper crust of Boston (his mom). Meanwhile, a second task force, headed by Alec Baldwin, is also trying to get Nicholson and can’t get a handle on why they are thwarted at every turn. DiCaprio is “erased” from police files, purposely gets arrested, and infiltrates Nicholson’s organization, which is populated by colorful, brutal goons (Ray Winstone, David O’Hara), in order to identify the mole. Meanwhile, Damon keeps screwing Baldwin’s pooch.
A cat-and-mouse hunt ensues, as Damon searches for DiCaprio and vice versa. Damon is also dating a psychologist (Vera Farmiga) who treats cops and ex-cons, including DiCaprio.
Almost to a person, the performances are rich and rough. DiCaprio is now in full bloom, grown out of the Titanic baby face and having just previously offered two nuanced and substantial performances in The Aviator and Blood Diamond. Nicholson is bloody and funny, and, well, Nicholson.
All the supporting characters are strong and natural save for Farmiga (she’s too feminine for the role and when she becomes infatuated by a clearly unstable DiCaprio, it is unconvincing) and Wahlberg, who, ironically, was nominated for best supporting actor. He yells an awful lot and delivers a few speeches, but volume and line memorization do not deserve a nomination. Wahlberg seems uncomfortable and masks it with rage. And once again, Matt Damon does all the heavy lifting and gets none of the credit. His turn as the fatherless boy who is being manipulated by Nicholson is alternately frightening and heartbreaking, yet he remains a very charming sociopath.
The picture whizzes by. Scorsese effortlessly paces what could have been a morass of a story, providing his signature quick-cut expositions to perfectly chosen music (The Stones, Badfinger, Allman Brothers).