Character He Plays: Captain Oliver Charles Queenan
Boston Guy's Assessment: Terrible. It sounds like he was trying to do his best JFK but ended up sounding exactly like Mayor Quimby from The Simpsons.
There's a part at the end of The Departed where Martin Sheen is asked, "Where's you boy?" and he says, "He's studying law at Notre Dame" in the worst Boston accent possible and it's the most painful part of the movie. I bet people spit on Martin Sheen when he visits Boston.