21. Stephanie Seymour
Issue: March 1991, February 1993
Stephanie is one of a few representatives from the golden age of the Sports Illustrated Swimsuit issue to make this list. Her colleagues included Elle MacPherson, Rachel Hunter, and Cindy Crawford.
Seymour was the wild child. Her two Playboy appearances almost line up with her tumultuous two-year relationship with Axl Rose, possibly the least dateable man in rock and roll at the time. It did not end amicably.