Unnecessary Debate: Battle of Boston Part 2 (Semifinals)



If you haven’t already, catch up on the first round before reading on!

Great films have already fallen. Some superstars and icons find themselves on the outside looking in while others still have a chance at the greatest victory of their careers. We’re left with four films spanning ten years, four directors, eight Oscar victories, and two Afflecks. To briefly recap, The Departed and Good Will Hunting are the top seeds and advanced with relative ease, but Gone Baby Gone and Mystic River had to to fight hard for their victories, against The Town and The Verdict, respectively. Keep in mind that this competition takes into account more than box office numbers and awards totals. We want to know which movies get at the heart and soul of our city, though this of course requires high entertainment value and impressive performances. By the time you reach the end of this page, only two will remain. Can the favorites move forward to do battle, or will one of the underdogs prevail? To the battles!


#1 The Departed (2006) vs. #5 Mystic River (2003)


You, the faithful reader person reading at least this sentence, may recall me ranking The Departed as my top Best Picture winner of the past ten years. That, however, was months ago, and once again this competition is not of the same nature as those Oscar rankings. Moreover, Mystic River wasn’t there to stare Scorsese’s film in the eye and dare it to cross it. Clint Eastwood’s film was nominated for the top prize, and losing out to Return of the King is certainly not something to be upset about, seeing as EVERYONE lost out to Return of the King. Still, there is no denying that The Departed doubled River’s trophy total (4 to 2) and eclipsed it in terms of acclaim and attention. So is there hope for the wily 5-seed? Can it push the tournament favorites to the brink?


Three men, contemplating their Battle of Boston mortality.


First, some controversy does surround this pool’s top seed. This controversy does not take away from The Departed‘s prestige and success, but it could very well play a role in this battle for the heart of Boston. The Departed is, in fact, a remake. Not an adaptation or homage but a remake. Of the 2002 Hong Kong thriller Infernal Affairs, and to some extent its 2003 prequel and sequel. Now of course our Americanized version ranks higher on IMDb’s top 250 and other domestic charts, but this is not due to a lack of merit for Infernal Affairs. In fairly typical American fashion, our film is almost an hour longer and far more garish with regard to its language and tone. To be clear, I still love The Departed. With all my heart. The star-studded cast makes the violence and vulgarity work and the length bearable. I bring up the original film only to ensure it gets the credit it deserves as a pioneering crime drama and to certify this Boston battle as a fair fight.

Mystic River, on the other hand, comes from the mind of a man raised on the streets with which he sets his stage. Dennis Lehane, as mentioned in the quarterfinals, has a knack for using his hometown as a character woven into complex tales. The film’s overlapping relationships and recollections derive from the thoughts of a man with a keen awareness of this area and the types of people that inhabit it. Mystic River is, in many ways, the San Antonio Spurs of this tournament. Starting with its quiet, tough leader, the movie goes about its business without catering to the flimsy whims of the masses. Three experienced men share the spotlight (Sean Penn, Tim Robbins, and Kevin Bacon) while drawing on decades of triumphs and failures in the business. To be succinct, the movie and its major figures came into this battle with a chip on their shoulder, and they’re not going to let young bucks like Leonardo DiCaprio and Matt Damon walk all over them.


Bang, bang.


Source material aside, both films contain interweaving, overlapping, twisting, and turning plots that can be difficult to follow and chardacters with various levels of loyalty, substance abuse, and willingness to break the law. When it comes down to it, The Departed is pure fun — great actors getting the chance to curse and cheat and lie and show off their accents, though I’m still not convinced that anyone besides DiCaprio really gives a standout performance (Jack Nicholson does not count because he is CRAZY). The plot is loud and crowded and frenzied while Mystic River‘s is a slow burn, a methodical drama smoothly washing over you. Scorsese’s film ends in anarchy and chaos while Eastwood’s closes with a simmering resolution to leave things as they are, for better for worse. Maybe The Departed is still more fun to watch, but the originality and authenticity of Lehane’s story pushes it over the edge and into the final showdown.


Winner: Mystic River


#2 Good Will Hunting vs. #6 Gone Baby Gone


Well, it’s still sort of Ben Affleck vs. Ben Affleck! And there’s a chance at an all-Dennis Lehane final! Subplots abound, but let’s try to stay focused on the matchup at hand, people. More so than in the battle above, these opponents are vastly different. The first semifinal was filled with dramatic irony and ironic tragedy, but here we have two films with very little in common, save for trusty Affleck. They also enter this penultimate bout with very different mindsets. On one side stands the favorite for which this site is named, having fulfilled expectations by reaching this point. On the other lies Gone Baby Gone, the tournament darling who is simply happy to be here. This satisfaction following its upset of The Town could spell trouble for GBG, but it could also signal a side ready to play loose and free with another upset on its mind. Only the next few paragraphs will tell.


(Above) Not loose and free.


There is a greater disparity in prestige between these two than in the other clash: one Oscar nomination for the underdog while GWH has nine nominations and two fairly major victories on which to lean. With bigger stars and a more solid legacy, the two-seed simply has greater fame and recognizability. Everyone has heard or said “How do you like dem apples?” You don’t hear people spitting out lines from GBG, though it does have a sharp script littered with clever interactions and entertaining law enforcement chatter. In fact, if one is to rely on the tired stereotypes of Boston as a gritty, tough place, then you’d have to point towards GBG as the more Bostony of the two movies. Take, for example, this chunk of Patrick Kenzie’s (Casey Affleck’s) opening lines:

      “I lived on this block my whole life; most of these people have. When your job is to find people who are missing, it helps to know where they started. I find the people who started in the cracks and then fell through. This city can be hard. When I was young, I asked my priest how you could get to heaven and still protect yourself from all the evil in the world. He told me what God said to His children. “You are sheep among wolves. Be wise as serpents, yet innocent as doves.”

The script, thanks to Lehane, is filled with these types of considerations. Kenzie and those around him exist within strong, unyielding barriers tying them to the people and places they’ve known all their lives. Strong bonds do exist in Van Sant’s movie, in which loyalty ties Will to his goofy friends. Will, however, experiences a far different fate than Kenzie. Like Lehane’s character, Will has been hardened by his upbringing, but along come Minnie Driver and Robin Williams to open up his world. We laugh when he makes a Harvard grad student look foolish and maybe smirk when he goes toe to toe with Williams’ Sean, but we smile (and, ahem, cry) when he isn’t home in the final moments, when he has “to see about a girl.”


FREEDOM, eventually.

The city and its oscillations pull Will and Chuckie and the gang together, but the movie does not simply leave us thinking that they will endure because of their friendship but rather shows how uplifting friends can be. Will turns 21, so his friends give him a car, the vehicle with which he escapes Boston not for money or the glory for which his intellect calls but for Skylar. In GBG, we see what can happen in the decay of a city — the alienation, chaos, and rage that plague Lehane’s creations, but in GWH we see something more hopeful, if not realistic. People brought together by birth and proximity pushing each other forward rather than allowing them to mire in place, an uplift not unfamiliar to fans of the men who grace the green beneath the Monster or of those grinding for one another in the bright lights of TD Garden. Maybe, in the years between GWH and Lehane’s work, our world grew a little darker, calling for stories of perseverance like that of Patrick Kenzie. But that’s only a middle ground, somewhere between despair and freedom, between detachment and unshakable brotherhood. Both reflect casts and crews that have a feel for the city, but GWH leaves us with the liberating hope that GBG‘s characters cannot even comprehend. For knowing that our city wants to end up smiling, Matt and Ben move onward.

Winner: Good Will Hunting



The final Battle of Boston will come quick, so stay vigilant. Complain away.



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About Author: Brian McMahon

Brian is an author and co-founder of GoodWillWatching. He likes to write and is deathly afraid of bugs. His Great American Novel, not yet titled or existent, will be shocking the world some time or another. He once stayed up for two days straight because of poor information regarding the arrival of Halley’s Comet, which was not due for approximately 57 years. You can follow him @bm1313 on Twitter, or in real life from a safe distance.



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