We are currently updating the images of previous Pimp of the Year winners. Check back regularly for more edits.
Click on the image to read the summary of why each person won their Pimp of the Year title.
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- 1861 Abe Lincoln
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- 1935 – Franklin D. Roosevelt
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- 1953 Queen Elizabeth II
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- 1971 John Holmes
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- 1974 Dolemite
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- 1976 Statler and Waldorf
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- 1977 Darth Vader
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- 1978 Zombie Gary Busey
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- 1980 Ronald Reagan
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- 1981 Papa Pimp
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- 1982 Mickey Mouse
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- 1983 Mr. T
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- 1984 Optimus Prime
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- 1985 – Ronald Reagan
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- 1986 – Ronald Mack Donald
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- 1987 Robo Pimp
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- 1989 Homer J Simpson
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- 1990 Saddam Hussein
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- 1992 Superman
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- 1993 – Bat Boy
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- 1994 Ronald Mack Donald
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- 1995 Snowman
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- 1996 Hillary Clinton
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- 1997 Cartman
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- 1998 Bert
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- 1999 Jerry Seinfeld
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- 2000 Donald Rumsfeld
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- 2001 Osama Bin Laden
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- 2002 Jimmy Carter
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- 2003 George Bush
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- 2004 Ronald Mack Donald
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- 2005 Pope John Paul II
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- 2006 SnowMan Jones
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- 2007 Barack Obama
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- 2008 KrazyMan
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- 2009 Afro Ref
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- 2010 Rated R Afro Star
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