The Sound of Music cast - then and now. The Von Trapp Family Lodge is in Stowe, VT. The real Trapp family, which SoM is inspired by, started and ran this lodge. I have friends who stayed there a few weeks ago.
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.
Doris Day in Calamity Jane. The song 'Once I had a Secret Love' was used in a pantomime production upcountry in Kenya when I was 9 and it made a great impression. I didn't see the film until many years later. A favourite film.