Complete list of Playmate of the Year winners since the PMOY became an annual fixture in Playboy. Photos are included for single every Playmate of the Year winner, listed alphabetically for your convenience, providing a Playmate of the Year reference for Playboy fans and curious parties. On this list, you'll find Playmate of the Year winners who became mainstream figures like Jenny McCarthy, Sara Jean Underwood, and Anna Nicole Smith, along with less high profile Playmates of the Year likeLooking for a list of Playmates of the year? You are in exactly the right place. This PMOY list is all about the most famous Playmates: the ones who were crowned PMOY. Who do you think is the all time hottest Playboy Playmate of the Year? Being the Playboy Bunny of the Year is an enormous honor for Playboy models, earning their centerfolds places in history. Check out this list of all Playboy Playmates of the year and see them in all their glory!