2. Bo Derek
Issue: March 1980, August 1980, September 1981, July 1984, December 1994
By 1984, Bo Derek was already the star of men's fantasies worldwide, thanks to her previous Playboy shoots and her breakthrough role in 10. It was when she posed as a cowboy sucking a cigar that men realized they'd be okay with a little role reversal and they'd love to be her "damsel in distress."