Ashley Judd at the 1998 Oscars
Air date: March 23, 1998
Judd's dress was a sexy number slit all the way up to her private area. Remember that old rhyme that goes, "I see London, I see France..."? Well, it only works if there are underpants to see. So, it would have not worked for Ashley Judd on this particular star-studded night as she strutted to the mic on stage.