Daddy’s a King: Understanding Whitey Bulger and Boston in Film

“When I was your age, they used to say, ‘You can become cops, or criminals.’ Today what I’m saying to you is this: When you’re facing a loaded gun, what’s the difference?”

– Frank Costello, The Departed


Next weekend, Black Mass hits theatres.

It will be a dramatization of something much more dramatic – this is no knock to the movie, but instead an admission that entertainment and Oscar bait (even deserving bait) can never match the real thing, especially when that ‘real thing’ is a man like Whitey Bulger.

The former ‘Most Wanted’ American, who was allowed to infest his hometown of Boston and – specifically – South Boston, did just that to the fault of the very institution that writes those most wanted lists, the FBI. Whether the Federal Bureau of such-and-such condoned or allowed or supported Bulger’s killing and fu*king and thieving and looting and disembowelment of Boston is up for discussion, gossip and interpretation. There’s some truth to it – there’s some exaggeration to it. Just how much of either is not for me, or anyone in the audience, to decide or rule on.

But what’s obvious is, several (or a few) of the very people who were responsible for serving and protecting the citizens of Boston did neither, either intentionally or because they chose to look another way.

Bulger reached inside his hometown and ripped out its guts and larynx, selling both for temporary and selfish profit.

Here’s a snip from John Liam Policastro and his article, South Boston Is Too Ugly For Reality TV, for VICE:

“During this period of the mid 1990s, South Boston was still living many lies that were about to be exposed. Southies would boast that theirs was the safest neighborhood in Boston to raise a family or walk around at night. Drugs were not a plague on the community and were not tolerated, the story went. By being a tight-knit community, they were able to police themselves and keep the bad elements out. Then came the news that reputed South Boston Mob boss James “Whitey” Bulger, long believed a townie Robin Hood, had not only been living a second life as an FBI informant, but that he was using that status to conceal his many twisted endeavors. With the Feds protecting him over the course of his ruthless reign, he literally got away with murder. Nineteen times, actually. Including a young woman he is alleged to have strangled. Not only did he know of drugs in the neighborhood, he even had a hand in it.”

Johnny Depp will crush it, because Johnny Depp crushes everything. Even in throwaways like The Tourist or Mortdecai (not that I saw it, I’ll admit), Depp is infinitely better than someone who belonged in movies like that would have been. Depp could sell Hyundais and he’d sell them well. He’s the man who’s played a Pirate of the Caribbean four times and Hunter S. Thompson twice. He’s played Edward Scissorhands and J.M. Barrie, both to critical acclaim, because he’s very, very good at his job. He’s like Sean Penn if Sean Penn didn’t know he was Sean Penn. (More on Sean Penn below. Sean Penn.)

But I’ve always felt, anything that’s based on a true story, even a documentary, is somewhat faker than fiction.

An admitted story, even one that’s made up or adapted or traced, can more easily tell the truth because it doesn’t have any duty to do so. It can make assumptions and theorize because it’s accountable only to itself and its audience. Contrast that with a documentary or a biopic, like Black Mass or Selma or Unbroken or Straight Outta Compton, which will be ripped apart or criticized or given the rolling eyes by the AV Club just because it leaves out a few tidbits that matter to select groups of people.

You try telling 40 years of someone’s life in 120 minutes. Chances are, you’d cherry pick a biased slab of material, too. And length isn’t important: I learned more about Pablo Escobar from the 30 seconds he was in Blow than I did over a whole season of Narcos. What’s the best Vietnam War movie I’ve ever seen? Honestly, probably Forrest Gump or The Deer Hunter, and those movies were in Vietnam for 15 minutes each. The Godfather told you as much about the mob’s place in Las Vegas as Bugsy or Casino did – even more, since Coppola’s film focused more on Nevada than it did on the Strip.

So anyway, here are the best movies about Boston – or at least the ones that come to mind, since there are too many – and the best movies about Whitey Bulger.

Why are these the best movies about Whitey Bulger? Because he’s not in any of them.

Mystic River

There’s no mention of Bulger in this criminally underrated movie, still the best of Clint Eastwood’s directing career – the post-Western portion of his directing career, that is. In fact, there’s nobody even pretending to be a renamed version of Bulger.

The only guy who comes close is Sean Penn’s (see, SEAN PENN!) character Jimmy Markham, a small-time tumbler and former gangster with a beck-and-beck tattoo to remind you, “Yeah, he’s retired but he could still kick anyone’s ass he wants to.”

Markham doesn’t rule Boston. He hardly even rules his own house or his convenience store. But in the world Mystic River shows, Penn is God.

And really, any movie about a kingpin or a dictator or Whitey Bulger, they’re all about God. The big man in the sky rules with unquestioned impunity and legitimacy – it’s like he’s ruled forever, since before you were born, and you don’t even know how he started.

That’s Bulger and that’s Jimmy Markham. In the movie, for those who know him, his name induces an understandable shudder every time it’s mentioned. And in the movie, Markham is trying to get better because he knows he really can’t – that’s what evil is, and that’s what good is, and they both play off each other. As Tim Robbins’ character says about his own condition, even as a victim, “once it’s in you, it stays.”

The Departed

A more direct interpretation of Bulger, The Departed simply renames him ‘Frank Costello’ and re-tells his story in a pretty ingenious adaptation of a Chinese film nobody really cares about anymore.

Jack Nicholson’s excellent in the film, even if his Boston accent isn’t. And while the movie is a little dated if you watch it fresh now, it knocked your socks off in 2006.

Everything Costello does in The Departed is a to-the-tee, almost Wikipedia-like entry on Bulger’s bio: the working with the FBI (while supposedly giving them nothing), the murder of two people by the ocean, the ordered murder of his right-hand man’s former girlfriend, the crooked cop he raised and continues to employ (who Matt Damon plays), and his status as a Robin Hood of South Boston who actually lives in a penthouse with the city’s most beautiful view.

Nicholson adds a little Chinatown to the role, but it’s perhaps the best movie to watch if you want to understand who Bulger was and what he meant.

(NOTE: The Departed is a Scorsese film, obviously. So if you’re thinking Marty should have been the guy to direct a Whitey Bulger film like Black Mass, don’t worry – he already did.)

Gone Baby Gone

Okay, you’re rolling your eyes…

Not only is this movie not about Whitey, but it doesn’t even contain a character based on him. Instead, though, turn to Gone Baby Gone as an exceptional look into what Bulger’s community was and is like – a study of the people and their city, and their simultaneously messed-up relationship, balanced and dangling between love and dysfunction.

Its base is about a murdered girl. But the web – the mother, the cops investigating, the police covering it up – is the real story. And by the end, you may just be questioning the good guy(s).

Monument Avenue

Full disclosure: I’ve never seen it.

But so what? You don’t need to know something to conclude it’s worth checking it. Gunaxn describes it as a “film about a group of Charlestown friends who see themselves as Robin Hoods – robbing from the yuppies for the good of their working class neighborhood.”

Robin Hood. That guy just keeps coming up, specifically in films about Boston, because it’s a stock way to reason why you’d rob and kill and just do a bunch of criminal things. Because even if you’re screwing over someone who isn’t actually rich or greedy, you can aways find someone poorer .

The Town

A smaller and less-powerful version of Bulger – at least, that’s what it seems, since Pete Postlethwaite’s Fergie owns nothing more than a flower shop.

But it’s clear, as the film progresses, that Fergie is more than just an old man “with a fu*ked up face” (as Ben Affleck puts it). He doesn’t just own a small shop in a beaten-down, nowhere neighbourhood – he owns lives. And he’ll do anything to keep them, which he makes clear to Affleck’s character when he naively and giddily announces his plans to leave a life of crime. (“I’m gonna clip your nuts, like I clipped your Daddy’s,” he tells him, in the video below.)

Postlethwaite’s character is pure and proud evil. He’s also a protector; just a very jealous, violent one.

And really, aren’t God and the Devil sort of the same guy?