15 Hottest Playmates Of The Year : When Playboy cancels its nude photo shoots next year, it will be a major change for the entertainment. Documentary · Add a Plot» Playboy Playmates of the Year: The 80's (). Unrated | 55min They All Laughed · Playboy Wet & Wild: Slippery When Wet. 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.