Hugh Hefner’s Wives, Girlfriends & Children

Hugh Hefner

Hugh Hefner, the legendary founder of Playboy died on Wednesday at his iconic Playboy Mansion near Beverly Hills, Calif. He was 91.

Hefner was born April 9, 1926, in Chicago to Glenn Hefner, an accountant, and Grace Hefner, a teacher.

In 1944, after graduating from high school, Hefner joined the U.S. Army as a writer for a military newspaper. Following World War II, and while working as a promotional copywriter at Esquire magazine, he began toying with the idea of publishing a men’s magazine.

Hefner founded Playboy in 1953 with $600 of his own money and built the magazine into a multimillion-dollar entertainment empire that at its 1970s peak included TV shows, a jazz festival and a string of Playboy Clubs whose cocktail waitresses wore bunny ears and cottontails.

Over the years, the legend of “Hef” only grew as he bedded hundreds of young women, married a few of his magazine’s “Playmates” and cavorted on reality TV shows with a stable of girlfriends less than a third his age.

At his peak, every man dreamed of being Hugh Hefner and every woman wanted to be with him. Let’s meet some of the women who were in his life one way or the other.



Hef’s first wife was Mildred Williams, best known as Millie. The couple tied the knot in 1949 and welcomed two children during their 10-year-marriage; Christie and David

Millie who attended Northwestern University cheated on Hef before their wedding. At the time he was away in the army. During their marriage she allowed him to be with other women out of guilt for her infidelity. The two ended in divorce in 1959.

Hugh Hefner

30-years after his divorce in 1989, he married second wife, Kimberly Conrad, a 26-year-old former Playmate of the Year with whom he fathered two boys. The couple who were 36-year-appart, separated in 1998 and eventually divorced.

Hefner and third wife Crystal Harris began dating in 2009. The two became engaged in 2010 but broke up the engagement just days before the wedding in 2011. The two eventually got back together and were married on December 31, 2012. Crystal who was 26 at the time of the wedding, became his third and last wife.

Crystal was born April 29, 1986; the Arizona native is the daughter of Ray Harris and Lee Lovitt. The blonde began modeling while attending San State Diego University and also appeared in The Girls Next Door. She was Playboy playmate of the month in December 2009.


Hugh Hefner once said he had easily slept with over a thousand women and though there is no way to know for sure, he did have a few girlfriends.


He dated former model, actress and singer Barbi Benton from 1969 until 1976.


From 2000 until 2011 he and model and actress, Brande Roderick were also an item.


Hefner had a seven-year relationship with model Holly Madison. The two were together from 2001 until 2008. While dating Holly, Hefner simultaneously dated Bridget Marquardt and Kendra Wilkinson. The trio became known in the reality TV show, The Girls Next Door.

Bridget Marquardt and Hefner dated from 2002 until 2009, while he and Kendra dated from 2004 until 2008. After the show, all of the girls went on to start in their own projects.


From his first marriage, Hefner fathered two children: daughter Christie Hefner (born 1952) and son David (born 1955).


Christie Hefner –who graduated summa cum laude from Brandeis University with a bachelor’s degree in English and American literature in 1974 –served as chairman and chief executive officer of Playboy Enterprises, until 2009. She is currently chairman of the board of Hatch Beauty.

David Hefner works as a computer analyst with his own computer consulting company in Northern California.

From his second marriage, he is also the father of two, sons: Marston Glenn (born 1990) and Cooper Bradford (born 1991).


Martson Hefner –a leader of the Human Rights Student Task Force –has always chosen to stay away from the Playboy Enterprises. In 2012 he made headlines after he allegedly got into a fight with his Playboy playmate girlfriend, Claire Sinclair.


Cooper Hefner is Chief Creative Officer at Playboy Enterprises, founder and former CEO of upstart media company HOP, and a member of the California State Military Reserve.