Playboy’s Playmates of the Year
Playboy began naming a Playmate of the Year in 1960, choosing Miss December 1959 Ellen Stratton. Many famous Playmates were named Playmate of the Year, including Anna Nicole Smith (PMOY 1993), Jenny McCarthy (PMOY 1994), and Hef’s former wife Kimberly Conrad (PMOY 1989).
One interesting exception–possibly the most famous Playmate of them all, Pamela Anderson, who was beaten for PMOY 1991 by Lisa Matthews.
| Year | Issue | Playmate | Video |
| 1960 | Miss December, 1959 | Ellen Stratton | |
| 1961 | Miss April, 1960 | Linda Gamble | |
| 1962 | Miss September, 1961 | Christa Speck | |
| 1963 | Miss December, 1962 | June Cochran | |
| 1964 | Miss December, 1963 | Donna Michelle | |
| 1965 | Miss December, 1964 | Jo Collins | |
| 1966 | Miss October, 1965 | Allison Parks | |
| 1967 | Miss November, 1966 | Lisa Baker | |
| 1968 | Miss September, 1967 | Angela Dorian | |
| 1969 | Miss January, 1968 | Connie Kreski | |
| 1970 | Miss November, 1969 | Claudia Jennings | |
| 1971 | Miss August, 1970 | Sharon Olivia Clark | |
| 1972 | Miss January, 1971 | Liv Lindeland | |
| 1973 | Miss January, 1972 | Marilyn Cole | |
| 1974 | Miss February, 1973 | Cyndi Wood | |
| 1975 | Miss May, 1974 | Marilyn Lange | |
| 1976 | Miss August, 1975 | Lillian Muller | |
| 1977 | Miss November, 1976 | Patti McGuire | |
| 1978 | Miss September, 1977 | Debra Jo Fondren | |
| 1979 | Miss November, 1978 | Monque Saint Pierre | |
| 1980 | Miss August, 1979 | Dorothy Stratten | |
| 1981 | Miss December, 1980 | Terri Welles | |
| 1982 | Miss November, 1981 | Shannon Tweed | |
| 1983 | Miss October, 1982 | Marianne Gravette | |
| 1984 | Miss September, 1983 | Barbara L. Edwards | |
| 1985 | Miss December, 1984 | Karen Velez | |
| 1986 | Miss May, 1985 | Kathy Shower | |
| 1987 | Miss November, 1986 | Donna Edmonson | |
| 1988 | Miss December, 1987 | India Allen | |
| 1989 | Miss January, 1988 | Kimberly Conrad (Hefner) | |
| 1990 | Miss November, 1989 | Renee Tenison | |
| 1991 | Miss April, 1990 | Lisa Matthews | |
| 1992 | Miss September, 1991 | Samantha Dorman | |
| 1993 | Miss May, 1992 | Anna Nicole (Vickie) Smith | |
| 1994 | Miss October, 1993 | Jenny McCarthy | DVD |
| 1995 | Miss February, 1994 | Julie Lynn Cialini | DVD |
| 1996 | Miss March, 1995 | Stacy Sanches | DVD |
| 1997 | Miss December, 1996 | Victoria Silvstedt | DVD |
| 1998 | Miss December, 1997 | Karen McDougal | DVD |
| 1999 | Miss January, 1998 | Heather Kozar | DVD |
| 2000 | Miss October, 1999 | Jodi Ann Paterson | DVD |
| 2001 | Miss April, 2000 | Brande Roderick | DVD |
| 2002 | Miss September, 2001 | Dalene Kurtis | DVD |
| 2003 | Miss August, 2002 | Christina Santiago | DVD |
| 2004 | Miss April, 2003 | Carmella Decesare | |
| 2005 | Miss December, 2004 | Tiffany Fallon | DVD |
| 2006 | Miss June, 2005 | Kara Monaco | DVD |
| 2007 | Miss July, 2006 | Sara Jean Underwood | DVD |
| 2008 | Miss January, 2007 | Jayde Nicole | |
| 2009 | Miss March, 2008 | Ida Ljungqvist | |
| 2010 | Miss April, 2009 | Hope Dqoraczyk | |
| 2011 | Miss October, 2010 | Claire Sinclaire | |
| 2012 | Miss April, 2011 | Jaclyn Swedberg | |
| 2013 | Miss April, 2012 | Raquel Pomplun | |
| 2014 | Miss December, 2013 | Kennedy Summers | |
| 2015 | Miss May, 2014 | Dani Mathers | |
| 2016 | Miss December, 2015 | Eugena Washington |
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