Now we start getting into the meat and potatoes of Boston movies. The cream if the crop. The creme de la creme. Or any other cliche you find fitting
5) The Fighter (2010)
While not technically set in Boston you get the "Boston feel" right off the bat in the opening sequence with boxer Mickey Ward (Mark Wahlberg) and his brother Dicky (Christian Bale) walking down the street and everybody in town cheering for them and giving them high fives. In my experience very few actors can pull off the Boston accent but I think by 2010 actors are starting to realize the subtlety in the dialect as Bale and Ward mother (Melissa Leo) pull it off very well.
While there have been a bajillion boxing movies from Raging Bull to Rocky to Cinderella Man, what The Fighter actually lands a few punches and brings something new to the genre. Director David O. Russell used special cameras to film the boxing scenes to make the fights look like an HBO fight you would watch on Pay-Per-View.
The Fighter follows the story of the rise of Mickey Ward and his addict trainer/brother Dickey as Mickey struggles between gaining respect in the boxing world and trying to balance his family dragging him down with his super hot girlfriend Charlene (Amy Adams) with wanting his brother (who really is a phenomenal trainer) to be in his life.
The Fighter follows in the decade long trend of being that gritty, blue collar, salt-of-the-earth Boston movie that we've come to grow and love over the years. Plus, you know, its got those great accents which includes Wahlberg as being one of the best actors in Hollywood to do a Boston accent (him being from Boston certainly helps)
4) Mystic River (2003)
The movie that really started the whole Boston movie trend and the first of two author Dennis Lehane who sets his stories in Boston and the surrounding area.
Mystic River, directed by the great Clint Eastwood, follows the story of Jimmy Markum (Sean Penn) as he deals with the murder of his daughter and Jimmy's relationship between two of his childhood friends now-cop Sean Devine (Kevin Bacon) and local blue collar guy and victim of childhood rape Dave Boyle (Tim Robbins).
The movie follows both Penn and Bacon as they search for Jimmy's daughters murderer, Bacon with his partner played by Laurence Fishburne use their legal resources while Penn and his gang of thugs use their underground resources and the movie is a slow burn as the mystery unravels with some of the acting performance of not only 2003 but of the decade.
If you still did not understand what "the city of Boston as a character" means look no further than this movie. I think you could set this same exact story in another city but I don't think it would have had the same powerful effect. The streets shape this movie and the characters and I think it's just a great movie.
3) Gone Baby Gone (2007)
I'm sure I am in the small minority who likes Gone Baby Gone over Mystic River but out of the two Dennis Lehane stories on this list, I prefer this story better.
Directed by Ben Affleck, who was raised in Cambirdge, Massachusetts and starring his little brother Casey (who plays Patrick Kenzie) I like this movie as a Boston movie better because I think the Affleck brothers add their unique experience to this movie which enhances the Boston-ness.
The best non-Bostonian Boston accent comes from Amy Ryan (who plays Helene McCready. You may know her as Michael Scott's girlfriend in The Office). The movie was filmed on location in Massachusetts neighborhoods and one day on set Amy Ryan, who was in full character, tried to get on set and the security guards wouldn't let her on because they thought she was just a local who showed up for the day and tried to weasel her way on to a Hollywood movie set.
The movie follows Patrick and his girlfriend Angie (played by the atrocious Michelle Monaghan. Seriously, she's awful in this movie and far and away the worst part of this movie) and their search for Helene's daughter along with police officer Remy Bressant (Ed Harris) and chief of police Jack Doyle (Morgan Freeman). In true Dennis Lehane fashion, the movie is a mystery of what happened to this little girl and as the movie progresses the more strings get unraveled.
The movie is great because it wrestles with the question, "What is best for a child?" Is it a shitty parent who happens to be the child's biological parent and does care for the child or a non-shitty non-biological person who also cares for the child. You may not agree with what Patrick does in the end or if Helene really does change, but I think it's an interesting argument the movie makes.
2) The Departed (2006)
The second greatest Scorsese movie ever behind Goodfellas? Maybe, maybe not but there is no doubt how awesome this movie is. On of the best most awesome bad-ass scene comes a shot in the beginning of the movie between Billy Costigan (Leonardo DiCaprio) and a barfly
Barfly: What are you drinking?I think DiCaprio's a great actor but good lord is that man horrible at accents (see: This movie, Blood Diamonds) and Jack Nicholson (Frank Costello) didn't even attempt a Boston accen. However, Matt Damon and Mark Wahlberg put on great Boston accents (as always).
Billy: Cranberry juice
Barfly: It's a natural diuretic. My girlfriend drinks it when she's got her period. What, do you got your period?
Billy then stares at his drink, stares back at the barfly, and then smashes his drink full of cranberry juice in the barfly's face
If there was ever any doubt that The Departed was a Boston Movie then look no further than Nicholson's source for his character: the recently captured Whitey Bulger.
The movie, based on the Hong Kong flick Infernal Affairs follows the story of two moles (one from the police force into Costello's gang and another from Costello's gang in the police force) as they search to find each other. And in true Scorsese fashion, lots of violence and awesomeness ensues.
1) Good Will Hunting (1997)
In one of the first scenes in the movies the group of friends Will Hunting (Matt Damon), Chuckie Sullivan (Ben Affleck), Morgan O'Mally (Casey Affleck), and Billy McBride (Cole Houser) are watching a little league baseball game when one of the friends state, "Let's go to Kelly's" In the very next scene the boys are driving and Chuckie is hassling Morgan about Morgan's roast beef sandwich and how Morgan can't pay for his sandwich right now.
I bring up this scene because there is nothing more Boston than Kelly's. Whenever I visit another buddy of mine's college I always want to try local cuisine and not some chain restaurant. If you ever go up to Boston, go to Kelly's. A few weeks ago my family and I went up to Boston to visit family and we ate Kelly's as much as we could. They have the best lobster rolls ever which is one of the greatest sandwiches ever. Also, its just a great anecdote to show you (as if you needed explaining) how GWH is a Boston Movie.
The movie was written by Affleck and Damon and directed by Gus Van Sant (who hasn't done anything good since, or really before). The movie follows Will Hunting who is a genius and one of the smartest people in the world but he refuses to be anything more than a janitor solving the hardest math problems ever at M.I.T. Through his relationship with his therapist Sean Maguire (Robin Williams) and his girlfriend Skylar (Minnie Driver) Damon attempts to overcome years of physical and emotional childhood abuse and to reach his genius potential. The movie is not cliche and Damon gives the best performance of his career. The story doesn't feel sappy or overdone or like a "typical Hollywood" movie and The 'Bright' One considers this movie the best movie ever made.
There are not many Boston movies and I have seen most of them. If I did not see the movie, I did not put it in on the list. Two movies that will probably make this list once I see them are The Friends of Eddie Coyle (19973) [thank you for the suggestion by GOI fan Bryan Hernandez] and The Verdict (1982) [A movie that have come up on essentially every single list I have researched].