I love all the old John Hughes type stuff...
Pretty in Pink
St. Elmos Fire
The Great Outdoors
Ferris Buellers Day Off
Some Kind of Wonderful
Licence to Drive
Can't Buy Me Love
Adventures in Babysitting!
(Of course, I'm probably the only one who watches it and says, "LOVE her hair!" )
Oh, and that makes me think of Cocktail! Really bad movie, but fun!
I have to say, though, that I rented St. Elmo's Fire a couple of years ago and just found it depressing. I loved it at the time, particularly the music.