Surprisingly, Hef has only been married twice: once, in 1949 to Mildred Williams, whom he met while at University of Illinois; and again in 1989. Barbi Benton was Hef's first official "girlfriend" after divorcing Williams in 1959. The two met at a Playboy Afterdark event in 1969, when Barbi was just 19, and went on to date for seven years. We nominate Carey Mulligan to play Barbi.
Photo by Mikael Jansson. Interview, April 2010.
Unsurprisingly, Hef came under fire during the women's movement in the '60s and '70s. We choose lawyer and activist Catharine MacKinnon as our representative of second-wave feminism, who worked to expose and eliminate sexual harrassment in the workplace. MacKinnon also campaigned against pornography, seeing it as a means of perpetuating sexism—a topic that is particularly pertinent to Hef. We'd love to see Michelle Williams as MacKinnon.
Photo by Mikael Jansson. Interview, April 2011.
We're not going to put Jude Law in prosthetics to play Hef in his later years. Instead, we'd like to cast Robert Redford, shown here wearing a plaid shirt in 1994. Redford in plaid, what more could you want? Alas, Redford will probably have to substitute this outfit for pajamas to portray Hef.
Photo by Albert Watson. Interview, September 1994.
Hugh Hefner has four children, two with each of his wives. His eldest daughter, Christie Hefner, took over from her father as CEO of Playboy Enterprises at the end of the '80s and recently stepped down (2009) to pursue charity work. We would like Melanie Lynskey to play Christie when she starts running her father's company.
Jayne Mansfield! If only she'd been born a decade earlier. While Mansfield started her career with the unfortunate nickname of "the working man's Marilyn Monroe," the figure that made her famous quickly became outdated and Mansfield's star quickly faded during the 1960s. Mansfield first appeared in Playboy in 1955. Her eldest daughter, also named Jayne Mansfield, posed for Playboy in 1976—the first second-generation Playboy model. We think that busty Brit, Alice Eve, has the figure for Mansfield.
We think that Jude Law would be perfect as a young(ish) Hugh Hefner. Law has something of twinkle in his eye that oscillates between boyish and sleazy. With some Hollywood makeup and grooming, we think Law could easily portray Hef during the '50s, '60s, and perhaps even the '70s.
Photo by Sam Taylor Wood. Interview, July 2001.