1953 Marilyn Monroe
Technically not “Playmate of the Year” for 1953 since they had not begun to use the moniker until 1957, but we weren’t about to do a post of Playboy’s covers and not include the “Blonde Bombshell.”
1957 Lisa Winters
The first PMOTY, thought they did not begin to award it annually until 1959.
1959 Joyce Nizzari
1960 Ellen Stratton
1961 Linda Gamble
1962 Christa Speck
1963 June Cochran
1964 Donna Michelle
1965 Jo Collins
1966 Allison Parks
1967 Lisa Baker
1968 Angela Dorian
1969 Connie Kreski
1970 Claudia Jennings
1972 Liv Lindeland
1973 Marilyn Cole
1974 Cyndi Wood
1977 Patti McGuire
1978 Debra Jo Fondren
1979 Monique St. Pierre
1980 Dorothy Stratten
1981 Terri Welles
1982 Shannon Tweed
1983 Marianne Gravatte
1984 Barbara Edwards
1985 Karen Velez
1986 Kathy Shower
1987 Donna Edmondson
1988 India Allen
1989 Kimberley Conrad
1991 Lisa Matthews
1992 Corinna Harney
1993 Anna Nicole Smith
1994 Jenny McCarthy
1995 Julie Lynn Cialini
1996 Stacy Sanches
1997 Victoria Silvstedt
1998 Karen McDougal
1999 Heather Kozar
2000 Jodi Ann Paterson
2001 Brande Roderick
2002 Dalene Kurtis
2003 Christina Santiago
No that isn’t 2003’s PMOTY Christina Santiago on the cover. It created a controversy when they did it but in 2003 Playboy’s editors decided to put “celebrity” Sarah Kozer from reality show Joe Millionaire instead. They chose to keep the PMOTY honor a mystery with the answer inside.
2004 Carmella DeCesare
2004’s cover continued the trend of hiding the PMOTY inside in favor of a celebrity on the cover. This would continue off and on for a few more years.
2005 Tiffany Fallon
2006 Kara Monaco
2007 Sara Jean Underwood
2008 Jayde Nicole
2009 Ida Ljungqvist
2010 Hope Dworaczyk
2011 Claire Sinclair
2012 Jaclyn Swedberg
2013 Raquel Pomplun
2014 Kennedy Summers
2015 Dani Mathers