Playboy Magazine founder Hugh Hefner died Wednesday surrounded by friends and family at the Playboy Mansion. While building his lifestyle empire, Hefner also became quite the ladies man.
Hefner has been married three times and has dated a number of Playboy bunnies since 1949. While he has claimed to have slept with over 1,000 women in his 91 years of life, only some have been able to call themselves his girlfriend and even fewer his wife.
Keep reading to see the most prominent women who have been in Hefner’s life.
Hugh Hefner married his first wife Mildred Williams in 1949. They met at Northwestern University.
Williams admitted to cheating on him before their wedding when he was in the army.
"I had literally saved myself for my wife, but after we had sex she told me that she'd had an affair. That was the most devastating moment in my life," said Hefner in 2007 to the Daily Mail.
The couple stayed together for a another decade, but divorced in 1959. The had two children together, Christie and David. Christie Hefner was the Playboy Enterprises Chairman and CEO for 20 years until she stepped down in 2008.
Hefner dated Barbara Lynn Klein from 1969 to 1976 and convinced her to change her name to Barbi Benton.
Benton appeared on the cover of Playboy in 1969, 1970, 1972, and 1985. After dating Hefner, she married real-estate developer George Gradow in 1979.
Shannon Tweed dated Hefner briefly after being named 1982 Playmate of the Year.
The "Falcon Crest" star dated Hefner until she started a relationship with "Kiss" singer Gene Simmons, who were married in 2011. They have two children together.
See the rest of the story at Business Insider