Dissatisfied with the type of roles that were on the market, Damon and Ben Affleck got together to write this screenplay, which saw them take home an Oscar.
Both starred in the film, but Damon took the lead as a streetwise janitor who's never too far away from trouble, but just happens to be a maths genius. Not only did the pair manage to craft compelling characters, but they also capture a vivid, believable Boston neighbourhood.
Brainiac Damon? The Oscar-winning writer seems at home playing a supersmart, but modest, guy.