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4. The Departed (2006)

When the Academy finally woke up and awarded Martin Scorsese an Oscar for Best Director and Picture, it did so for this thrilling, violent Boston crime drama featuring an amazing cast, from Jack Nicholson and Leonardo DiCaprio to Matt Damon, Mark Wahlberg and Martin Sheen. The theme becomes clear early on. In the Departed, there are no true heroes and there are no true saviors. Those that are fall by the wayside quickly, the innocent are discarded - killed, or shoved aside. The most evil triumph for the most part, or at least get away with so much before they are stopped that by the time they are, it is too late to feel like you’ve accomplished anything meaningful.

Featuring an acidic soundtrack and an iconic performance by Nicholson, the movie weaves in and out between truth and deception as it tells the story of a corrupt cop who is really a mafia mole, and a mobster who is in reality a good cop, himself a mole. The lies and double crosses create anxiety, tension and one of the most iconic elevator scenes and denouements of all time. Marty wasn’t kidding around with this one, and the bodies were dumped all over that city by the Bay.

3. Legally Blonde (2001)

There is space for some light-heartedness in this list, and if ever a romantic/girl comedy deserved a spot on a Boston list it is Reese Witherspoon’s classic, Legally Blonde. Perhaps not occupying the same space as Mean Girls or The Devil Wears Prada in the pantheon of 2000s girl power films, Legally Blonde can arguably by named their grandmother (and itself, the daughter of Clueless and the bridge between the 1990s and the 2000s).

In the well-known plot, Elle Woods is dumped by her boyfriend for being too dumb, and in revenge she applies herself and gets into Harvard Law School. And what could be more Boston than the first American University itself (one that, apparently, lets candidates in based on the nakedness of their admissions videos)? The movie then features it all, a light-hearted courtroom drama with hilariously unrealistic but genuinely surprising twists, stereotypically vicious lawyers and law students, and undemanding allies, in the downtrodden neighborhoods of Boston.

The sequel moved our heroine to Washington, but it likely won’t make any list about great D.C. movies. It is the original that was a breath of fresh air and has achieved iconic status with time.

2. Gone Baby Gone (2007)

Everything that L.A. Confidential did for the L.A. movie genre, Gone Baby Gone, Ben Affleck’s directorial debut, did once over. Before he was trying with all his might to win Academy Awards, Affleck directed this deeply personal, surprisingly moving, and incredibly nuanced about crime, love, and betrayal. He extracted some of the best performances of Casey Affleck and Amy Ryan’s careers. It features stunning and unexpected twists and a jaw-dropping finale by the usually reliable Morgan Freeman. In between, the movie weaves in and out of several iconic Boston neighborhoods, from Quincy to Dorchester, and shows you the underside, crime and poverty-ridden neighborhoods of the city.

Gone Baby Gone is a tense, taut thriller. In a way, it is obvious that Affleck took cues from Scorsese’s tones and techniques for the attempt to humanize the criminals. But the younger and more sensitive Affleck gives his characters a more human, emotionally dimension that Scorsese’s robotically evil players do not have.

Affleck has not yet, in my mind, topped his directorial debut, but here’s hoping.

1. Mystic River (2003)

Undoubtedly my favorite Boston movie of all, however, is Clint Eastwood’s tense psychological thriller Mystic River. The movie is based on the novel by the same name by author Dennis Lehane. Not coincidentally, Lehane also penned Gone Baby Gone. Dude knows his Boston drama.

But where some of Affleck’s novice traits are visible around the edges of his film, Mystic River is Eastwood at perhaps the height of his career (yes, he won it all the following year for Million Dollar Baby, but to me Mystic River was his last stunning masterpiece). The movie tells the harrowing story of the kidnapping and murder of Sean Penn’s character’s daughter. As he and the police search for her, dark secrets will be revealed and the true nature of some of the evil and feeble characters will surprise you. With Oscar-winning performances by Penn and his feeble brother, Timothy Robbins (and a nominated turn by the hypnotic Marcia Gay Harden), the movie keeps you guessing, and dreading.

All the time, Eastwood puts his finger on the mood of the lower middle class Irish neighborhoods of the city, without ever explaining what it is that has turned these once loving families and people into vicious, unrepentant animals. Maybe it is the decay of their culture, the downturn of their city. Maybe it is the lack of hope inherent in their humanity.

Or maybe one day they woke-up and forgot what it’s like to be human.

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