T.S.
When we went on vacation a few years ago I brought a three pack, Breakfast Club, Sixteen Candles and Pretty in Pink. My kids were 17, 15 and 12 at the time. I thought these movies might be dated but my kids loved them, especially the 17 and 15 year old, The Breakfast Club being their favorite! And they love, love, love Ferris Bueller's Day Off, as do I.
They also (all three) watched The Outsiders in school and loved that (not John Hughes but of that era.)