Probably the most famous up-skirt moment ever is the scene in "The Seven-Year Itch" in which a gusty New York air-vent blows up Marilyn Monroe's dress.
Her husband at the time, Joe Di Maggio, was shocked and reportedly struck Marilyn. He felt disgraced that his wife's knickers were seen in public (remind you of someone?).
Marilyn divorced him short after.
http://www.youtube.com/watch?v=6yX4IjBg-XM
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