Loose Ends, Unrealistic, Too Long

Rating: 4/10 (7 October 2006)

The movie had a shot at being good and maybe even great, but "The Departed" departs from reality, leaves loose ends, has outrageous plot holes, and is ultimately forgettable, rather than haunting.
Let me outline it for you...
Two kids grow up to be "Staties" (Mass State Troopers). One kid planted there by the mob (Matt Damon), the other kid chooses to be there as a revolt to his family (Leonardo DiCaprio). Both actors gave amazing performances.
DiCaprio fits the image of a wise guy, and an eventual fall out - so he is placed undercover with the Mob (Led by Jack Nicholson -- also incredibly excellent).
Damon (practically raised by Nicholson) as a mole in the state troopers constantly informs Niholson that he is about to be caught, thereby providing him with enough getaway time. DiCaprio of course keeps giving away Nicholson's position. Eventually, Both sides learn there is a mole and both sides ask Damon to figure it out. As such, Damon has a large conflict of interest in trying to find himself, and has no access to the under-covers who have been placed in the mob.
Here's where the movie gets bad, stupid, sloppy, ugly.. whatever you want to call it... Damon starts dating a psychologist working for the police, and DiCaprio starts seeing the same psychologist as a patient. DiCaprio eventually ends up at her doorstep and sleeps with her. She has no apparent moral dilemma with the fact that she is cheating on her cop boyfriend and sleeping with who she thinks is a thug.
Marky Mark -- great performance, and in the end, is completely wasted, and there is no explanation as to why he does what he does at the end of the movie.
To make matters more confusing, Nicholson is also an FBI informant. Huh? This subplot was not needed and made no sense. I don't believe the FBI would have the highest man on the mob food chain on their payroll.
Near the end of the movie, DiCaprio gives the psychologist an envelope and tells her to open it in two weeks or sooner if something happens to him. Well something does happen to him, and guess what? We never find out what is in the envelope. So, why did he give it to her? I just don't know.
More sub-plot -- the psychologist gets pregnant. One might assume she is made pregnant to add conflict as to who's baby it might be. In the meantime, she shows an ultrasound and declares that it is a boy (which by the way, cannot be determined until about 16 weeks. So, why was she made pregnant? I don't know.
As the movie moves along, you begin to think maybe there's a twist with the psychologist -- maybe she's running the show behind the scenes, but instead, we are just left hanging with nothing to take home.
All this being said, the movie is entertaining but it's too long and eventually loses itself in it's continual unfolding subplots that go nowhere.