Ferris Bueller's Day Off - Matthew Broderick is Ferris Bueller and Alan Ruck is Cameron Frye (Side-note, I've been told by others that I look a lot like Cameron. If you have a Red Wings jersey, I'd like to borrow it for Halloween.
Stalag 17 is a 1953 war film which tells the story of a group of American airmen held in a German World War II prisoner of war camp, who come to suspect that one of their number is an informant. It was adapted from a Broadway play.
Meg Ryan's Brownstone and Bookstore in "You've Got Mail"