BOSTON - Well, it's been five weeks! As such we now arrive at the end of the countdown. Here are the two greatest Boston movies ever made.

2. The Departed

Few needle drops were as thrill-inducing in the history of cinema as when the Dropkick Murphys came into play at the climax of The Departed, Martin Scorsese's 2006 Boston crime epic. Telling the story of duplicitous police work and mafia connections and untrustworthy bedfellows, The Departed is a rewatchable classic of Scorsese's and it won the Oscar for Best Picture back when it came out.

The cast is stacked. Matt Damon, Leonardo DiCaprio, Jack Nicholson, Mark Wahlberg, Martin Sheen, Vera Farmiga, Alec Baldwin. I can keep going! But it's more than just the cast. It's that the city is portrayed both realistically and reverentially throughout the film. It's the crackling, quotable dialogue. It's the jaw-dropping plot developments. It's the undeniable connection to Whitey Bulger. The Departed is one of the best blends of authenticity and straight-up fun in Boston's cinematic history.

1. Good Will Hunting

It should be no surprise that the top two movies both star Matt Damon. But this is the one who put Boston's greatest star on the map. Good Will Hunting was a 1997 directorial effort from Gus Van Sant, off a screenplay by Damon and Ben Affleck. It was a breakout smash hit that earned $225 million at the box office, netted nine Oscar nominations (including Best Picture), and launched its young actors into superstardom.

Affleck and Damon won the Oscar for Best Original Screenplay and they thanked Boston roughly eight thousand times in their acceptance speech. After all, the movie couldn't have been made without the city. So many iconic locations are used to tell the story of Will Hunting, a Southie janitor and math genius who receives guidance from Sean Maguire, played by Robin Williams. Williams also picked up a trophy and the bench in the Boston Public Garden remains a tribute to that beautiful bench scene in the film.

If you haven't seen Good Will Hunting, watch it again soon. You'll feel all the emotions you felt the first time. It's the best Boston movie and that's undeniable.

What did you think about the list? Have any disagreements? After all, there are so many Boston films to choose from!

  1. Good Will Hunting
  2. The Departed
  3. The Town
  4. Manchester by the Sea
  5. The Social Network
  6. Mystic River
  7. Spotlight
  8. Gone Baby Gone
  9. Fever Pitch
  10. Black Mass

Image via Wikimedia Commons