Phenomenal.

Rating: 9/10 (15 December 2007)

Even through about ten viewings, The Departed manages to be a highly engaging, suspenseful and thrilling film that's easily one of the most entertaining films I've ever seen. Scorsese creates an entire ensemble of interesting (some more so than others) characters that make every second just as fun and enthralling as the rest. When we switch from Costigan to Sullivan it never loses or gains entertainment value and its steady level is higher than practically any other film around. There's a wonderful mix of humor involved as well, coming primarily from Mark Wahlberg, Alec Baldwin and Jack Nicholson (more in the character's reactions to Nicholson than the man himself). Everyone in the cast is brilliant from DiCaprio and Damon all the way down to Alec Baldwin and Ray Winstone (though I've never been too big on Vera Farmiga and thought she was a thousand times better in that year's Running Scared).
In my first viewings of The Departed, I knew it was wildly entertaining but I always thought it was a little shallow and the characters lacked depth. But this viewing helped me see that what I originally thought was a thrilling story of undercover deception is really an intricate study of the loneliness and mental breakdown that occurs when you decide to live a lie. As William Costigan (Leonardo DiCaprio) and Colin Sullivan (Matt Damon) delve further into their life of being an undercover criminal and an undercover cop, respectively, they become so much more lonely and their psyche continually falls apart. While these two character's lives are polar opposites, they are quite similar at their center. They are both morally decent men who live a life of crime for unfortunate reasons; Costigan obviously because he is an undercover cop but Sullivan seems to be a good man at his heart but lives his life of deception out of loyalty to Frank Costello (Jack Nicholson) who was always a surrogate father to him after he lost his own. Of course they do have their contrasts which I thought came primarily in their way of making decisions. Costigan is indecisive, paranoid and is never confident in his decisions but Sullivan has snap reflexes and can make an insanely tough decision in a second with no hesitation. But in the end they are more similar than they are different; they even have romantic interest in the same woman. Ultimately it's their loneliness that links these two men; which Scorsese beautifully shows in the shots of Sullivan sitting in his office alone in the dark having to live with the horrific decisions he's made in his life (further proof that he's a morally decent man unlike the purely evil Frank who shoots a woman dead and his only remark is that she fell funny).
So while the film is still probably the most entertaining I've ever seen and is stylish, fun and completely enthralling my original belief that it was hollow was quite incorrect. It's a remarkable study of the toll that a life of lies can take on a person and is highlighted by two phenomenal performances that perfectly immerse into these characters. In fact every actor fits perfectly into his character. It never feels like you're watching Leonardo DiCaprio, Mark Wahlberg and Alec Baldwin but you're watching the characters unfold this story. Even in ten viewings it still manages to be completely suspenseful (Damon and DiCaprio sitting silently on the phone with each other, both knowing that the person on the other side is the rat, still had me holding my breath) and wildly entertaining. There's never a dull moment in this magnificent picture that I love more and more every time I see it, and that love was significantly increased in this viewing. I don't think any words can do the story justice, but there is so much depth and intricacy in there that I never saw before. And of course William Monahan does a perfect job of adapting the originally Asian story into the streets and people of Boston. Amazing in every way.