Number one has to be "The Blues Brothers"; it has everything- great music, comedy, car chases, and it was filmed in my hometown.
Next, I guess is "The Princess Bride"- LOVE this one.
More, in no particular order:
Singing in the Rain
Little Shop of Horrors
The Right Stuff
Armageddon
Dances With Wolves
My Big Fat Greek Wedding
The Breakfast Club
Animal House