As you may know, we at GWW come from a magical land — the land of the Charles and the Sox and the laughable accent. In the past decade or so, many great movies have taken place in and around Boston, so naturally we had to set out to determine the best one. Below you will find the first round of the Battle of Boston, eight movies squaring off in a single-elimination pool, with victors determined by their entertainment value and a sort of ambiguous Bostonyness. By narrowing the field to eight, I forced myself to leave off some notable films. The Fighter is a GWW favorite but fails to qualify due to its actual location being Lowell, MA instead of Boston. The Social Network worked its way into the discussion, but it falls short partially on merit and partially due to it not being a “Boston movie,” with much of the story taking place in California and our eastern home not actually playing much of a role. Movies like Ted and Fever Pitch crossed our minds, but unfortunately we have to make cuts somewhere. You can probably think of others, and we’re happy to hear your gripes, but for now I will make due with these eight. The rankings came about from rigorous algorithming based on pedigree, awards, coin flips, and predilections. Commence!
#1 The Departed (2006) vs. #8 The Friends of Eddie Coyle (1973)
As a 1-seed should, The Departed cruises through its first round matchup, though let us not diminish the accomplishment of simply reaching this tournament. The Friends of Eddie Coyle may very well be the least known film in the field, but it stands strong among the best crime movies of the ’70s and has certainly had an impact on Boston movies released in the past four decades. As Eddie, Robert Mitchum helped cement the film’s gritty, tough aura. If Peter Yates’ work had found a less formidable opponent, it may have had the potential for an upset, but The Departed simply has too much firepower, given the four-star performances delivered by Matt Damon, Leonardo DiCaprio, and Mark Wahlberg. I’ll go into more detail on Martin Scorsese’s Best Picture winner in the semifinal round, but for now it still looks like the favorite, unscathed through the first round. There’s something to be said for the thoroughbred running as strong as expected, BUT we are far from the stretch run. It’s not how you start…
Winner: The Departed
#2 Good Will Hunting (1997) vs. #7 The Boondock Saints (1999)
You’ve probably realized that Good Will Hunting is a favorite around here…but before you go scrolling down expecting it to win handily, CHECK YO SELF. It just so happens that GWW also adores The Boondock Saints. For a movie that barely made it to theaters, and left them quickly, Saints has done incredibly well, gathering an immense cult following due to its poetic violence and quotability. Willem Dafoe is usually a sign of an entertaining movie, and that trend continues here. Dafoe doesn’t just steal scenes in Saints – he devours them. While the sequel to this flick was a big mess of ‘meh,’ fine actors such as Norman Reedus, Billy Connolly and Willem Dafoe give an otherwise tired concept an artful, demented and funny beauty. Who doesn’t like an entertaining tale of vengeance? One could argue the film being more Bostony than GWH. The city plays a huge role in the aesthetics and narrative of each movie, and both Damon and Affleck and Troy Duffy capture the beats of the people populating their fictional hub. However artful and clever the bloodbath, though, Saints digs deep into the seedy underbelly while GWH paints a more romantic or hopeful picture. Matt Damon, Ben Affleck and Robin Williams won their Oscars for good reasons; their movie was life-changing for both many viewers and for the writing duo themselves. Without the movie, we simply do not have some of the other movies on this list. It seems unlikely that the two pals would have become such enormous stars if not for the inventive and intellectual story they crafted with director Gus Van Sant. Once again, more profound thoughts will be provided in the next round on our admittedly adored namesake. Saints, always the scrappy underdog, kept the game close early on, but there’s no Vermont magic happening here.
Winner: Good Will Hunting
#3 The Town (2010) vs. #6 Gone Baby Gone (2007)
The battle within the battle! Ben Affleck vs. Ben (and Casey) Affleck! Both movies received one Oscar nomination, for supporting actors (Jeremy Renner and Amy Ryan, respectively), both had Affleck as director and screenwriter, and both are quite good, to be simple. Gone Baby Gone was Affleck’s directorial debut, and it didn’t receive nearly as much buzz or money as The Town. I, however, am here to be fair and thoughtful, and I smell an upset. Gone Baby Gone is the first but not the last adaptation of a Dennis Lehane novel to appear in the bracket, and the author’s incredible eye for action and the ebbs and flows of Boston have a profound effect on the movies created from his work. Lehane’s lifelong experiences in the area have augmented his ability to craft detailed suspense stories, something that certainly made Affleck’s jobs easier.
A lot of people were upset that The Town didn’t get more Oscar attention, especially for Affleck as director. Others (me) think it was a great action movie that got what it deserved and question whether or not the lingering bitterness about the “snub” helped Affleck steal his Argo Best Picture win from Silver Linings Playbook. All of this makes determining who moves on to the semifinals very difficult. Both Renner and Ryan were very deserving of their nominations, but what about the rest of the casts? Casey may very well be a better actor than big brother Ben, and Morgan Freeman and Ed Harris round out a nearly flawless cast in Gone Baby Gone. The Town boasts plenty of big names, too, but Rebecca Hall and Jon Hamm never quite felt right in their roles, not to mention Blake Lively’s polarizing performance. Also, in a Boston movie battle, one must consider the Bostonyness: The Town is littered with great accents and memorable locales, but Affleck’s first directing effort, powered by Casey’s superb performance and the immaculately casted crew, strikes deeper into the heart of the city and its people. Dennis Lehane’s work helped push the film from solid to criminally underrated. Down goes Affleck, and onward he advances.
Winner: Gone Baby Gone
#4 The Verdict (1982) vs. #5 Mystic River (2003)
Ah, yes, the final battle of the first round. The fight to go up against The Departed when the field narrows to four. The Verdict boasts five Oscar nominations and a wonderful performance by my favorite actor of all time, Paul Newman. Mystic River flaunts six nominations and two wins (for Sean Penn and Tim Robbins) but no Paul Newman. The opponents are essentially locked in a dead heat. The seedings could have gone either way; it’s really too bad that some dumbass had to go and match these two up in the first round, à la Spain meeting the Netherlands in the group stage of the World Cup. What’s that? That game didn’t go so well for Spain? I digress.
Compelling stories drive each film. Barry Reed wrote the novel with which Sidney Lumet made his film, and Lehane of course wrote Mystic River, just in time for Clint Eastwood to pounce on the golden material. I have already admitted a bias towards Newman, but this is nearly cancelled out by my adoration for Lehane’s novel, one of the first “adult” books I can recall reading and loving. Paul Newman + alcoholic lawyer = production company’s fantasy, but even he cannot match the overpoweringly complex story of Mystic River, played out beautifully thanks to the aforementioned Oscar-winning performances along with strong supporting work delivered by Kevin Bacon and Marcia Gay Harden. Lumet had an incredible career (see 12 Angry Men and about 439 other great films), but he mainly dealt with the courtroom for The Verdict while Eastwood had the streets and scenery of the area to work with, besides the deep-rooted bonds between his three leading men. It truly pains me to hand Paul Newman a defeat this early in the tournament, but Eastwood and Penn and everyone else involved with Mystic River helped reinvigorate the very genre on which this bracket is founded. Without their moving work, we may have never gotten The Departed or Affleck’s hits. For that, we salute them.
Winner: Mystic River
Thanks for reading round one. Stay tuned for the semifinals, coming soon!