I personally am not aware that much of the real life Whitey Bugler, so can’t really vouch for the authenticity or how true it is to the actual story.
As a movie buff, I liked the movie, though it had a strong hangover of Goodfellas, Departed and Donnie Brasco.
The movie though not in the league of these gangster classics, is still pretty much a good effort. One of the prime reasons is Johnny Depp, in the main role. Personally, am a big fan of Depp, but of late most of his performances have not really required him to do much, except to wear masks, or wigs and act funny. After quite some time, good to see him in a role that does not require him to clown around( notwithstanding the fake looking prosthetics).
As a vicious, pyscopathic gangster he is brilliant, radiating menace, with his presence, a flick of the eye, or his measured way of speaking. Apart from the fact that Bulger seems to care for his son, there is not much that is redeeming about him. He is selfish and opportunistic, he plays along with his friend John Conolly( Joel Edgerton) a Fed agent, promising to help him out, but in reality uses him for his own selfish ends. He is ruthless, and pyscopathic to a level, where he gets rid of people, at the slighest suspicion. Matter of fact, he is the guy who does not even trust his own shadow.
The movie at one level runs as a morality play too, on the dangers of setting a thief to catch a thief. Conolly tries to use Whitey to get to the Mafia, by using him as an informant. However Whitey turns the tables on him, by providing him basically with junk information, and uses it as a cover to get his own with the rival Anguilo gang. In a sense, Conolly causes his own downfall, by getting too cozy with Bugler, maybe it could have been due to his childhood friendship with him. At one level, it could also have been a traditional Irish-Italian rivalry in 70’s Boston. Was Conolly soft on Bugler, due to the Irish factor, as well as the community feeling? And what exactly was the relationship between the Irish mob and the IRA?
This is where I feel, Black Mass falters somewhat, the performances are good, the scenes are well written, but director Scott Cooper, just tries to pack in everything, without really delving deep. The movie looks more like a montage of elements from earlier gangster movies, dinner table talks where hints are dropped, the brutal in your face violence, the liberal usage of the F-word, the protagonist going into a downward spiral and pulling others along. And the scenes are pretty good too, one particularly good one, where Bugler has a dinner talk with Conolly and his associate Morris, where he almost threatens Morris into fear and then does not. Or the scenes between Whitey and his brother Billy( Benedict Cumberbatch) a senator.
But the rivalry between Bugler and the Anguilo brothers is treated in a pretty sketchy manner. This is an area where so much could have been explored, especially the Irish vs Italian angle, but director Cooper just gives it a very cursory glance. Again the link between Bugler and the IRA is not explored in depth, we really do not know what motivates him to help them out. And due to this, it just remains a middlingly good movie, instead of a classic.
The performances are pretty good, apart from Depp, one more great turn is by Joel Edgerton, as the FBI agent who makes a pact with the Devil himself. Benedict Cumberbatch is however wasted in a role that really does not do much justice to his talent.