Highlights
- Hugh Hefner was a controversial figure who created the Playboy brand.
- Mildred Williams was Hefner’s first wife and played a role in shaping his beliefs on women and relationships.
- Hefner’s final resting place next to Marilyn Monroe solidifies his playboy legacy.
Playboy founder and mogul Hugh Hefner is a polarizing figure in American culture and history. Hefner created the Playboy brand in the 1950s and desired to develop the ultimate publication for men. As a result, Hefner’s efforts led to nurturing a controversial industry. Hefner and his Playboy brand have received significant backlash due to questionable allegations, especially since his passing in 2017, according to USA Today.
Hefner was, by all means, a lifetime bachelor. His countless girlfriends had interesting experiences dating the publisher and businessman. Though he was married three times throughout his life, Hefner cultivated a specific image and reputation. Hefner first married in the late 1940s and married his last wife in 2012, only five years before his death. Hefner’s wives will forever be tied to the Playboy founder, despite their own careers, personalities, and interests.
Who Was Hugh Hefner Married To?
In 1949, a young Hugh Hefner married Mildred Williams. The couple had met during their time at the University of Illinois Urbana-Champaign, before Hefner developed his controversial philosophies. Williams was the first woman he ever had intimate relations with. According to Heavy, Williams played a role in defining Hefner’s beliefs on women and relationships. While dating, Williams allegedly was unfaithful to Hefner, when he was serving in the U.S. Army. Once they married, Williams allowed Hefner to cheat on her as a result, according to the Hollywood Reporter.
Hugh Hefner’s Son Makes Bizarre Confession About What Playboy Mogul Would Eat For Dinner
Despite having millions in the bank, Hugh Hefner opted for a very strange (and cheap) meal when it came time for dinner.
Hefner and Williams had two children together:
- Daughter Christie Hefner (born in November 1952)
- son David Hefner (born in August 1955)
Their marriage was full of ups and downs, and was unstable. As a result, Hefner and Williams divorced in March 1959. It is known that Williams eventually remarried. However, not much is known about Hefner’s first wife. She has chosen to live a life out of the spotlight since her affiliation with the Playboy founder.
Throughout the 1960s and 1970s, Hefner enjoyed the companionship of numerous girlfriends as his business grew more popular. According to Fox News and US Weekly, some of the women he dated in this time frame include:
- Barbi Benton
- Marilyn Cole
- Sondra Theodore
- Lillian Mueller
In 1989, Hefner decided to finally marry again, despite his playboy-inspired lifestyle. That July, Hefner wed Kimberley Conrad, who was 36 years his junior. Conrad was only twenty-six when she married Hefner, who was in his early sixties. According to People Magazine, they met during a photo shoot test at the Playboy Mansion. Hefner and Conrad shared two sons, Marston and Cooper. According to US Weekly, they broke up in 1998, but were legally married until 2010. Cooper Hefner, Hefner’s youngest son, once served as the Chief Creative Officer of Playboy, before leaving his father’s brand.
Who Inherited Most Of Hugh Hefner’s Estate, And Where Are They Now?
Hugh Hefner’s children and his then-wife inherited most of his estate, but settling the will wasn’t as cut and dried as expected.
During his marriage to Conrad, Hefner claimed he was faithful to her, according to Daily Mail. Furthermore, Hefner alleged that Conrad was not loyal during their marriage. Once their relationship was unreconcilable, Hefner began to date again. According to US Weekly, women he dated in the 2000s include:
- Mandy and Sandy Bentley
- Brande Roderick
- Izabella St. James
- Holly Madison
- Kendra Wilkinson
- Bridget Marquardt
In 2012, Hefner married twenty-six-year-old Crystal Harris. They reportedly met at a Halloween event at the Playboy Mansion in 2008, according to The List. Once they met, Harris moved into the Mansion full time and started to date Hefner. Hefner and Harris were originally supposed to wed in 2011, but Harris called it off. They later rekindled their relationship and married on New Years Eve, according to US Weekly. Hefner and Harris had no children together, and Harris remained married to Hefner until he passed away in September 2017.
Hugh Hefner lived to be 91 years old and most likely enjoyed intimate relations until his final days. According to Playboy Enterprises, Hefner “peacefully passed away…from natural causes at his home, The Playboy Mansion, surrounded by loved ones.”
Why Hugh Hefner’s Final Resting Place Sparked Controversy
Hugh Hefner was just as controversial in death as in life. In 1992, he acquired a mausoleum crypt next to Marilyn Monroe at Westwood Village Memorial Cemetery for a staggering $75,000. The Playboy icon wanted to be buried next to one of the most famous women in entertainment history. However, there is more to the story.
Hugh Hefner Set A Strict Ban For His Family In His Inheritance That Needed To Be Followed
Hugh Hefner set a strict ban in his will for his family members who were inheriting from him that needed to be followed.
Hefner’s reasoning for his burial plans was quite simple. Monroe was Playboy Magazine’s first cover girl in 1953. According to Hefner, “I’m a believer in things symbolic. Spending eternity next to Marilyn is too sweet to pass up.” Some have found Hefner’s decision uncalled for and weird, however. Hefner and Monroe were never romantically linked, and there is suspicion that Monroe disliked Hefner. Furthermore, Monroe’s revealing images were not initially taken for Playboy, but the magazine acquired them once she started to get notoriety. She had taken them to make ends meet before her career blew up, according to NPR.
Being buried next to Marilyn Monroe further cemented the playboy legacy Hugh Hefner attempted to cultivate throughout his career. Hefner, who was married three times and dated countless women, is forever near Hollywood’s most famous leading lady and the woman who helped skyrocket the Playboy brand.
Source: NewsFinale
