In her twenties, Kimberly Conrad successfully convinced Playboy founder Hugh Hefner to make a 180-degree change in his views on marriage. However, the mom of two could not keep him from changing his stance on their relationship nine years later.
For 11 years, Kimberly lived next to Hugh Hefner while he dated Playmates like twins Mandy and Sandy Bentley, and Holly Madison. The latter became Girlfriend Number One on the E! reality series "The Girls Next Door," with Bridget Marquardt and Kendra Wilkinson.
The former Playmate of the Year is a grandmother to Betsy Rose, Marigold Adele, and Blossom Pearl and is an advocate for animal welfare.
Kimberly Conrad during Usher Hosts a Fundraiser for His New Look Foundation at Capitale in New York City, New York, United States. | Source: Getty Images
The Alabama Girl Became a Model at an Early Age
Kimberley Coonradt was born August 6, 1962, in Moulton, Alabama, and her family eventually settled in British Columbia, Canada. At 17, the 5' 9" teenager signed with John Casablancas' Elite modeling agency.
She caught the attention of Hugh by listing "blue jeans, midnight walks on the beach, and G-strings" as her favorite things in a questionnaire for a Playboy test in May 1987, and became Miss January 1988, and was dubbed Playmate of the Year some months later.
The model had a short-lived career as an actress in 1989, with bit parts in Michael Landon's "Highway to Heaven" and as a waitress in the prime-time soapie, "Falcon Crest."
Hugh Hefner, Marsden Hefner and Kimberly Conrad. | Source: Getty Images
Hugh Hefner Gave up His Bachelor Lifestyle for Kimberley – Kind Of
Hugh built his empire on the perception of being a bachelor partying from dusk to dawn, which made his decision to get married for the second time so surprising. PEOPLE reported on the July 1, 1989, wedding with the headline: "Hef Gains a Bride, Loses a Reputation."
Playboy's founder proclaimed that Conrad "turned him around 180 degrees" on marriage, and he proposed with a 5.5-carat diamond ring. The 26-year-old was unfazed by the criticism of her marrying her 63-year-old beau and said:
"The major reason Hef decided to marry is that he fell in love with me. We're both very much in love. And on top of that, we really, really like each other."
Before the wedding with 300 guests, Hef paid His Highness Prince Frederic von Anhalt, Duke of Saxony, Count of Ascania, $550 000 to knight Conrad, bestowing the title of "Princess" on her. Prince Frederic was not a noble by birth and had also paid for his title.
While the May/December couple welcomed their sons, Marston, on April 9, 199, and Cooper on September 4, 1991, the Playmates were still hanging around their home, just 'covered up' in bathing suits.
Years after, Conrad clarified the "common misconception" that she killed the party at the Playboy Mansion. She insisted that they "never refused anyone, ever," and she merely wanted to put an end to unexpected drop-in guests, requesting them to call ahead.
American model Rhonda Adams beside American magazine publisher Hugh Hefner (1926-2017) and his wife, American model and actress Kimberley Conrad and their sons, Marston Hefner and Cooper Hefner, attend the Playboy magazine Playmate of the Year presentation at the Playboy Mansion, in Los Angeles, California, 5th June 1995. | Source: Getty Images
The Couple Was Separated 11 Years before Their Divorce
When the couple separated in 1999, she moved into the next-door mansion with their two children and even appeared in the "E! True Hollywood Story: Hugh Hefner: Girlfriends, Wives and Centerfolds" in 2006, with no mention of a divorce.
Miss January 1988 rocked the status quo when she sued her estranged husband for $5 million over selling a house they co-owned. He refuted that she was owed money and maintained that she received a yearly amount of $250,000 per the prenup.
The founder of Playboy filed for divorce in September 2009 and filed a motion to have the child support payments halved. The divorce was finalized on March 11, 2010, the same year their youngest son turned 18.
Music producer Quincy Jones (C), with Kimberly Conrad and Oprah Winfrey (R) arrive at the 77th Annual Academy Awards at the Kodak Theatre. | Source: Getty Images
Kimberly Conrad's Life after Her Divorce from Hugh Hefner
After Conrad's divorce, she made a few more appearances in Hef's magazine. In November 2012, she was featured in the "Hef's Girlfriends" pictorial photographed by Bill Zehme.
She mostly lives a quiet life dedicated to animal welfare organizations around her home in Los Angeles, California, and has collaborated with People for the Ethical Treatment of Animals (PETA.
The vegetarian enjoys the outdoors and snowboarding. She posted an image of a hike with a male friend named Duke and her daughter-in-law to Griffith observatory in June 2017.
Conrad Recreated Her 1988 Cover Decades Later
In 2017, the chief creative officer of Playboy asked Kimberly, 54 at the time, to recreate her August 1988 cover. Making this request to a 50-something was not that peculiar, but the fact that her son Cooper was that chief creative officer is noteworthy.
The youngest Hefner has been a member of the US Air Force Reserve
The former Playmate was game, popping every last button on a white shirt to reveal a lace bra, as she did back in the '80s. The faux cover includes all the headlines of the original, markedly, "Kimberly Conrad, The new woman in Hef's life."
Kimberley Conrad's Two Sons Turned out Very Differently
Marston was arrested for an alleged attack on his girlfriend, Claire Sinclair, in 2012. He was ordered to stay away from the Playboy Playmate for two years and given 52 weeks in a domestic violence program.
His debut collection of flash fiction, "High School Romance," was released in August 2022. Per his bio, he is a professional backgammon player and avid gamer. He reportedly wrote a zombie novel under the pen name Marston Glenn.
Cooper Hefner followed his father and older sister Christie into Playboy Enterprises, where he served as chief creative officer. As of November 2022, he is a partner at the Texas-based firm Noble Capital Group. The British LGBT Awards recognized him in May 2018.
The youngest Hefner has been a member of the US Air Force Reserve since 2019 and was awarded a medal in 2022. He married "Harry Potter" actress Scarlett Hefner on November 4, 2019, and they have three daughters.
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