Starring: Ben Affleck, Robin Williams, Matt Damon, Minnie Driver
This classic follows Will Hunting who has a genius-level IQ but chooses to work as a janitor at MIT. When he solves a difficult graduate-level math problem, his talents are discovered by Professor Gerald Lambeau; who decides to help the misguided youth reach his potential.
2. The Departed
Starring: Leonardo DiCaprio, Jack Nicholson, Alec Baldwin
South Boston cop, Billy Costigan, goes undercover to infiltrate the organization of gangland chief Frank Costello. As Billy gains the mobster’s trust, a career criminal named Colin Sullivan infiltrates Costigan’s police department.
Starring: Morgan Freeman, Casey Affleck, Michelle Monaghan, Ed Harris
Private detective Patrick Kenzie is hired to trace a missing daughter in a tough Boston neighborhood where he’s lived all his life. Though, the real danger may be closer to home.
4. The Town
Starring: Blake Lively, Ben Affleck, Rebecca Hall, Jon Hamm, Jeremy Renner
Doug MacRayleads a band of ruthless bank robbers in Boston. Everything changes for Doug when he falls in love with a hostage, Claire Keesey; who lives in the gang’s neighborhood.
Starring: Leonardo DiCaprio, Michelle Williams, Mark Ruffalo
U.S. Marshal Teddy Daniels and his partner investigate a woman’s escape at Ashecliffe Hospital, an insane asylum located on a remote island. As the investigation deepens, Teddy realizes he will have to confront his own dark fears if he hopes to make it off the island alive.
– Richard Zarrilli, Jr.
Sources: IMDB Rotten Tomatoes Ranker