The story of gangster James "Whitey" Bulger is basically the story of Boston in the 20th century.
Bulger represented everything good and bad about Boston: he was fiercely loyal to family, ambitious, territorial, bigoted, shrewd, mean, and really good at staying quiet when it served his own interests. Anyone who lived in New England during Bulger's years at the top of organized crime could tell you that he was a kind of folk hero for the city: a fearsome killer, a charming neighbor, a brother to a powerful state senator, a supporter of the Irish Republican Army, a mob boss who conned the FBI into getting rid of his enemies for him, a highly problematic lottery winner. At the time, Bulger was kind of like Robin Hood, only he kept all the money for himself and everyone was pretty sure he strangled a bunch of people.
So it's weird that director Scott Cooper's adaptation of Black Mass, the quintessential book on Whitey Bulger, could practically be set anywhere. The Boston in this movie feels leached of all personality. Oh sure, there are Boston trappings here and there — a few good accents (Benedict Cumberbatch, Juno Temple) and a few bad ones (Dakota Johnson, Corey Stoll), a few exterior shots that are way too pretty for Boston in the '70s and early '80s. But none of Boston's frustrating, pugnacious provinciality comes into play; the character of the city just doesn't make it to the screen. (The Departed, which featured Jack Nicholson as a Bulger stand-in, was the most recent movie to get Boston right.)
Maybe part of the problem lies with Johnny Depp's performance as Bulger. Depp doesn't even try for the accent, instead settling for a modified Brooklyn with a touch of '30s gangster flick tossed in. His Bulger has the menacing part down right — a few scenes are super-tense — but he lacks the charisma that made the gangster one of the most beloved local celebrities of his time. The Bulger Depp portrays is pretty much always someone to be feared, making this a good performance but a bad portrayal of a real-life figure. Aside from a couple of early scenes where Depp is nice to some little old ladies, it's hard to understand why Bostonians would avidly scoop up newspapers with headlines that promised another installment in the ongoing soap opera that was Bulger's life. For years, Boston loved Bulger, and then for years after that, Boston loved to hate him.
If you think this is just obsessive regional nitpicking, you should understand that Black Mass doesn't even work very well as a generic gangster film. The movie isn't so much a narrative with consistent themes as a collection of scenes in which something happens, an agglomeration of roles played well (Jesse Plemons as a low-level mob enforcer, Peter Sarsgaard as the world's most neurotic sociopath) and poorly (Adam Scott in a bad mustache).
Cooper's direction lacks coherence and purpose; toward the middle of the film, Black Mass just becomes a string of executions of people who cross Bulger on some insubstantial issue, and all the price-fixing, horse-racing, gun-running, and other illegal activities referred to in the dialogue stay off-screen. It's a movie that's so obsessed with being serious and dark (we are, after all, finally in Oscar season, are we not?) that it forgets to give Bulger's outsized personality a little room to play. Neither his personality nor the city that his personality reflected can be found anywhere in Black Mass.♦