How exactly did this movie win the Academy Award for Best Picture? I like Scorsese and I like this cast, but The Departed is a giant, muddled mess. The movie starts off with some world building, introducing us to the world of South Boston in the 1970's, going so far as to use actual news footage from the period. There's a quick introduction of Jack Nicholson (who is a joy to watch in all his scenery-chewing grandure and almost saves the movie) and the Matt Damon character before flashing forward to the present and basically hooking up with the storyline of Infernal Affairs, the far superior Hong Kong thriller of which this film is a remake. Once we're on track with that story, it really becomes inconsequential what world or city this movie is set in, so all that setup in the first half of the film is wasted. The movie largely follows the same beats as the original, but changes the ending and some pivotal character moments, which makes me wonder if the filmmakers even understood what story they were trying to retell.
Oddly, there's a puff piece documentary on the DVD extra's that tries to connect the Nicholson character with Whitey Bulger, but the story of Bulger is not the story that is being told here. There may be some similarities shoehorned in, but The Departed remains a remake of Infernal Affairs no matter how you look at it. If the filmmakers wanted to tell the story of Bulger, they should have done just that.
Bold and large in scope, as one would expect from a movie directed by Martin Scorsese, but very good it ain't.