Best Boston movies since 1990
by iKindaLikeVanHalen | created - 11 Oct 2010 | updated - 30 Jun 2016 | Public- Instant Watch Options
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1. Good Will Hunting (1997)
R | 126 min | Drama, Romance
Will Hunting, a janitor at M.I.T., has a gift for mathematics, but needs help from a psychologist to find direction in his life.
Director: Gus Van Sant | Stars: Robin Williams, Matt Damon, Ben Affleck, Stellan Skarsgård
Votes: 1,069,133 | Gross: $138.43M
2. The Departed (2006)
R | 151 min | Crime, Drama, Thriller
An undercover cop and a mole in the police attempt to identify each other while infiltrating an Irish gang in South Boston.
Director: Martin Scorsese | Stars: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg
Votes: 1,423,122 | Gross: $132.38M
3. Gone Baby Gone (2007)
R | 114 min | Crime, Drama, Mystery
Two Boston area detectives investigate a little girl's kidnapping, which ultimately turns into a crisis both professionally and personally.
Director: Ben Affleck | Stars: Morgan Freeman, Ed Harris, Casey Affleck, Michelle Monaghan
Votes: 293,101 | Gross: $20.30M
4. The Town (2010)
R | 125 min | Crime, Drama, Thriller
A proficient group of thieves rob a bank and hold an assistant manager hostage. Things begin to get complicated when one of the crew members falls in love with her.
Director: Ben Affleck | Stars: Ben Affleck, Rebecca Hall, Jon Hamm, Jeremy Renner
Votes: 415,959 | Gross: $92.19M
5. Mystic River (2003)
R | 138 min | Crime, Drama, Mystery
The tragic murder of a 19-year-old girl reunites three childhood friends still living in Boston--the victim's gangster father, a detective, and the disturbed man they both suspect of killing her.
Director: Clint Eastwood | Stars: Sean Penn, Tim Robbins, Kevin Bacon, Emmy Rossum
Votes: 486,050 | Gross: $90.14M
6. Shutter Island (2010)
R | 138 min | Drama, Mystery, Thriller
Teddy Daniels and Chuck Aule, two US marshals, are sent to an asylum on a remote island in order to investigate the disappearance of a patient, where Teddy uncovers a shocking truth about the place.
Director: Martin Scorsese | Stars: Leonardo DiCaprio, Emily Mortimer, Mark Ruffalo, Ben Kingsley
Votes: 1,457,979 | Gross: $128.01M
7. The Boondock Saints (1999)
R | 108 min | Action, Crime, Thriller
Two Irish Catholic brothers become vigilantes and wipe out Boston's criminal underworld in the name of God.
Director: Troy Duffy | Stars: Willem Dafoe, Sean Patrick Flanery, Norman Reedus, David Della Rocco
Votes: 250,777 | Gross: $0.03M
8. Black Irish (2007)
R | 95 min | Drama
A teenage boy longs to win the attention of his emotionally distant father.
Director: Brad Gann | Stars: Michael Angarano, Brendan Gleeson, Emily VanCamp, Tom Guiry
Votes: 2,685 | Gross: $0.01M
9. What Doesn't Kill You (2008)
R | 100 min | Crime, Drama, Thriller
Two childhood friends from South Boston turn to crime as a way to get by, ultimately causing a strain in their personal lives and their friendship.
Director: Brian Goodman | Stars: Ethan Hawke, Mark Ruffalo, Brian Goodman, Amanda Peet
Votes: 13,233
10. Monument Ave. (1998)
R | 93 min | Crime, Drama, Thriller
A small-time hoodlum is divided between his conscience and loyalty to his boss when his cousin is murdered.
Director: Ted Demme | Stars: Denis Leary, Ian Hart, Jason Barry, Lenny Clarke
Votes: 1,891 | Gross: $0.33M
11. The Equalizer (2014)
R | 132 min | Action, Crime, Thriller
A man who believes he has put his mysterious past behind him cannot stand idly by when he meets a young girl under the control of ultra-violent Russian gangsters.
Director: Antoine Fuqua | Stars: Denzel Washington, Marton Csokas, Chloë Grace Moretz, David Harbour
Votes: 420,521 | Gross: $101.53M
12. What's Your Number? (2011)
R | 106 min | Comedy, Romance
A woman looks back at the past nineteen men she's had relationships with in her life and wonders if one of them might be her one true love.
Director: Mark Mylod | Stars: Anna Faris, Chris Evans, Ari Graynor, Blythe Danner
Votes: 87,457 | Gross: $14.01M
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