I loved Good Will Hunting..
My sis has a friend that lives in Harvard Square, and there are dudes there that sit outside the cafes there during the summer and all they do is play chess but you have to pay them like $5, and they're damn near impossible to beat unless you're some prodigy yourself. There was some old bum that played chess outside an au bon pain cafe there and he reminded me of the Matt Damon's character.