The Many Loves Of Hugh Hefner

    Lifelong ladies man Hugh Hefner finally married Crystal Harris on New Year's Eve. In honor of their recent nuptials, let's take a look at the other ladies in Hef's past.

    Mildred Williams (1949-1959)

    Donna Michelle (c. 1963-1964)

    Barbi Benton (1969-1976)

    Unknown Men (c. 1960s)

    Karen Christy (c. 1971)

    Marilyn Cole (c. 1971-1974)

    Lillian Muller (c. 1974-1976)

    Sondra Theodore (1974-1981)

    Carrie Leigh (1983-1988)

    Shannon Tweed (1982)

    Kimberley Conrad (1989-2010)

    The Bentley Twins (1999-2000)

    Brande Roderick (2000-2001)

    Tina Marie Jordan (2001-2002)

    Izabella St. James (2002-2004)

    Bridget Marquardt (2002-2008)

    Holly Madison (2003-2008)

    Kendra Wilkinson (2004-2009)

    Kristina and Karissa Shannon (2009-2010)

    Crystal Harris (2009-2011, 2012-)