Stars Matt Damon as a troubled math prodigy from Southie and Ben Affleck as his running mate, faster of mouth and slower of brain. Robin Williams is along for the ride as Damon's tortured-but-wise therapist. Remembered for Damon and Affleck's screenwriting Oscar and the apotheosis of Hollywood-on-the-Charles chic. For Boston cred, Williams reenacts Carlton Fisk waving the ball fair in the sixth game of the 1975 World Series. On the minus side, Damon takes the Red Line through Dorchester to get from MIT to Southie. That's possible if you want to double back in a cab, but highly impractical.
Pictured, Matt Damon (left) as Will Hunting and Robin Williams as Sean Maguire.