1. Gone With the Wind
2. West Side Story
3. Donnie Darko
4. The Princess Bride
5. Young Frankenstein
6. Rocky Horror
7. Monty Python and the Holy Grail
After #1 and #2, the order is subject to change depending on the mood I'm in. Right now I'm in a very Donnie Darko mood.
In fact the order of #1 and #2 may be because I saw both of those movies at a very young age. All the others were kind of during my so-called adulthood.