Hugh Hefner: Conflicting Facts About A Complicated American Icon

The life and legacy of Hugh Hefner cannot be undressed easily. The man behind Playboy created the “ideal woman” for 60 years. At the same time, he fought for gender and racial equality. Critics derided Hefner for his exploitation of the female body for profit. Friends and family praised him as a generous and caring soul.

Here is the complicated but true story about Hugh Hefner; how he was loved, hated, and broke racial and gender barriers through the power of the pen.

Mildred Williams Cheated On Hugh And Turned Him Into A Polygamist

Mildred Williams was Hugh Hefner’s childhood sweetheart and first wife. Before they got married, Williams told Hefner she cheated on him, then permitted him to do the same. Disillusioned, Hefner took Mildred up on the offer. In 1953 Playboy became a massive success, and Hefner made his lifestyle public, throwing lavish parties full of beautiful women. While alive, he claimed to have slept with thousands of women.

Photo Credit: Earl Leaf/Michael Ochs Archives/Getty Images
Photo Credit: Earl Leaf/Michael Ochs Archives/Getty Images

Hugh Hefner and Mildred Williams divorced after ten years together. They had two kids, Christie and David Hefner. It would be another 30 years until Hefner felt the urge to get married again.

Hefner Married “Playmate Of The Year” Kimberly Conrad In 1989

Thirty years after divorcing Mildred Williams, Hugh Hefner married 27-year-old “Playmate of the Year” Kimberly Conrad. The couple stayed together for 11 years, separating in 1999. They have two children; Cooper and Marston. After separating, Conrad and the boys moved into a house next door to the mansion.

Photo Credit: Jeff Kravitz/FilmMagic via Getty Images
Photo Credit: Jeff Kravitz/FilmMagic via Getty Images

The marriage wasn’t always amicable, and the divorce didn’t paint Hefner in a good light. He fought to have the alimony owed to Conrad reduced from $40,000 a month to $20,000. In 2009, Conrad sued Hefner for $4 million that she claimed he never paid under their prenuptial agreement.

Crystal Harris Was Saved By Hefner

In 2012 Hugh Hefner married his third and final wife; Crystal Harris. Twenty-six-year-old at the time of the marriage, Harris gushed about Hefner after his passing, ” He changed my life, he saved my life. He made me feel loved every single day. He was a beacon to the world, a force unlike anything else.”

Photo Credit: Dan Kitwood/Getty Images
Photo Credit: Dan Kitwood/Getty Images

Harris regarded Hugh Hefner as an “American hero.” For anyone thinking Harris married Hefner for his money, she only received a small portion of his $43 million fortune. Hefner had Harris sign an “ironclad” prenuptial agreement to make sure her love was real.

Hugh’s Son Views Him as a “Cultural Pioneer”

Hefner’s son Cooper paid his respects to Hugh, calling his late father a “leading voice behind some of the most significant social and cultural movements.” Now running the Playboy empire, Cooper plans to continue his father’s legacy of spreading positivity and protecting the First Amendment. Moreover, he wants the magazine to be one of the major forces for breast cancer awareness, remarking: “talk about a relevant Playboy Foundation.”

Photo Credit: Jeff Kravitz/FilmMagic, Inc
Photo Credit: Jeff Kravitz/FilmMagic, Inc

During the early days of Playboy, Hefner pushed a message of equality. In the 1960s, the magazine interviewed Martin Luther King Jr. It was the longest interview the civil rights leaders ever granted.

Playboy Interviewed Martin Luther King Jr. In 1964

In 1964 Hugh Hefner had Alex Haley, a black writer, interview Martin Luther King Jr. The civil rights leader won the Nobel Peace Prize, prompting Hefner to ask for the “sit-down.” The series of conversations was edited into one interview for Playboy. Running the article in 1965, it was the longest interview King Jr. ever gave.

Photo Credit: Alisdair MacDonald /Mirrorpix/Getty Images
Photo Credit: Alisdair MacDonald /Mirrorpix/Getty Images

The culturally significant interview was not the only time Hefner used Haley to push boundaries. In 1966 Hefner asked George Lincoln Rockwell, the founder of the American Nazi Party, for an interview. Rockwell agreed, as long as the interviewer was not Jewish. Hefner sent Haley, withholding his skin color from Rockwell. During the conversation, Rockwell kept his pearl-handled revolver on display, pointedly, for Haley to see.

Miles Davis Was the First Interview in Playboy

Playboy published its first interview in 1962. The subject was Miles Davis, and the interviewer was Alex Haley. The controversial conversation shocked society at the time. Davis opened up about his childhood, saying: “In high school, I was best in music class on the trumpet, but the prizes went to the boys with blue eyes.”

Photo Credit: Victor Crawshaw/Mirrorpix/Getty Images
Photo Credit: Victor Crawshaw/Mirrorpix/Getty Images

The inaugural interview sent sales of Playboy through the roof. It became so popular the magazine started a monthly segment of interviews with cultural icons. Suddenly Playboy became a magazine that was about more than scantily clad women. Going further, in 1991 the magazine broke another cultural barrier, featuring its first transgender playmate.

Caroline Cossey Become The First Openly Transgender Woman To Pose For Playboy

Caroline Cossey was twice featured in Playboy. The first time, in 1981, was after the actress starred in the James Bond film For Your Eyes Only. The second time, in 1991, was after the actress was publicly outed for being transgender. Born Barry Cossey, Caroline underwent gender transformation surgery in 1974. Shortly after her Playboy pictorial, a British tabloid outed her for being born male.

Photo Credit: Brendan Monks/Mirrorpix/Getty Images
Photo Credit: Brendan Monks/Mirrorpix/Getty Images

Ten years later, she approached the magazine about another appearance, this time as openly transgender. Hefner granted Cossey her wish. After he died, she said, “I think it spoke loudly of how respectful he was of the individuality of others. He certainly was with me.” Not everyone close to Hefner felt the same way.

Holly Madison Outs Hugh Hefner as a Misogynist

Most famous as one of Hugh Hefner’s live-in girlfriends, Holly Madison has been critical of Hefner since their break-up. In 2015, Madison published a tell-all book, Down the Rabbit Hole, revealing disturbing details about her time in the mansion. Hefner would make life miserable for his girlfriends, continually pitting them against each other in conflict and limited their contact with the outside world.

Photo Credit: Denise Truscello/WireImage
Photo Credit: Denise Truscello/WireImage

Madison claims that Hefner would move girlfriends to different bedrooms based on his own favoritism. He would leave the best photos of his girlfriend outside their doors every morning as a reminder to “be perfect all the time.” During parties, they were not allowed to leave Hefner’s table, and they were forced to go upstairs with him when he went to sleep. Some girlfriends would sneak back down to the parties to meet other men, but they would have to avoid the mansion’s video crew.

Suzanne Moore Called Hefner A Pimp And Was Sued For Defamation

After Hugh Hefner died, journalist Suzanne Moore stood by her allegation of him as a pimp. The comment made by Moore “long ago, in another time” was not received well. Hefner’s team threatened to take legal action. Moore wishes the case had gone to court, but it never did.

Photo Credit: Jules Annan / Barcroft Media via Getty Images
Photo Credit: Jules Annan / Barcroft Media via Getty Images

Today, Moore isn’t backing down. In a piece for The Guardian, she explains that it’s wrong to rewrite the history of a misogynist after he dies. Take the glitz and glamour away, and the facts are simple, “he was a man who bought and sold women to other men. Isn’t that the definition of a pimp?”

Kendra Wilkinson Recants Holly Madison’s Claims

Kendra Wilkinson moved into the Playboy Mansion when she was 18-years-old. When Hefner died she paid tribute, “He made me the person I am today. I couldn’t be more thankful for our friendship and our time together. I will miss him so much, but he will be in my heart forever.”

Gregg DeGuire/WireImage
Gregg DeGuire/WireImage

Wilkinson says she was not expected to be monogamous with Hugh. She kept her private life private, having affairs with younger men at hotels near the mansion. As long as her lifestyle never went public, Hefner allowed it. She says she can’t speak for Madison’s experience, but is grateful for her own and remained friends with Hefner until his death.

Christie Hefner Wouldn’t Have Another Father

Christie Hefner offered a resounding “No” when asked if she wished for another father. Looking back on her life, Hefner’s first child and only daughter said, “I didn’t feel burdened by it. It’s been a wonderful life.” The only aspect of her father’s legacy that Christie would like to carry on is being active in politics. Like her brother Cooper, she understands her position as part of the Playboy legacy makes this impossible.

Photo Credit: Joe Kohen/WireImage
Photo Credit: Joe Kohen/WireImage

As for allegations that her father treated women like lesser beings? For 26 years, she helped run the magazine and said, “It was very clear that the culture was one of respect — respect on every level.”

A Biopic About Hugh Hefner Was Canned After The Director Was Fired For Misconduct

The culture of Playboy was going to be explored in a biopic starring Jared Leto. The movie was canceled after director Brett Ratner was fired for several misconduct allegations.

Photo Credit: Ted West/Central Press/Hulton Archive/Getty Images
Photo Credit: Ted West/Central Press/Hulton Archive/Getty Images

Christie Hefner approved of the casting of Leto. She said he’s an impressive actor and has the “bone structure for it.” The cancellation of the movie doesn’t keep Christie up at night though. She is perfectly happy with American Playboy on Amazon Prime, shutting the door on the Playboy legacy.

Hugh Hefner Once Received A Razzie Nomination For Playing Himself

Hugh Hefner was nominated for a Golden Raspberry (Razzie) Award for playing himself in the 2010 comedy Miss March. The critically derided film didn’t initially have Hefner. In an early cut, Robert Wagner portrayed the icon. When his performance didn’t test well, the filmmakers went to Hefner, who was happy to poke fun at himself.

Photo Credit: Chris Polk/FilmMagic
Photo Credit: Chris Polk/FilmMagic

Given the negative awards attention, Hefner might regret the decision. Upon learning of his nomination, he took to Twitter, “I’ve been nominated for a Razzie for my portrayal of Hugh Hefner in Miss March. Maybe I didn’t understand the character.” Hefner lost the Razzie to Billy Ray Cyrus for the Hanna Montana Movie. That same year, Hefner won a much more meaningful award.

The First Ever “Founder’s Hero Of The Heart Award” Was Given To Hugh Hefner

In 2010 Hefner didn’t win a Razzie, but he did win the first ever “Founder’s Hero of the Heart Award.” Given to him by the Children of the Night foundation, the award recognized Hefner for his unwavering support. For over 30 years the organization helped to rescue children from prostitution rings.

Photo Credit: John Downing/Express/Getty Images
Photo Credit: John Downing/Express/Getty Images

Since Children of the Night was started in 1977, Hefner gave them his full support. In the press release for the award, he is credited with helping save over 10,000 children. Hefner saved more than just children.

He Saved a Species of Rabbit

Never sleeping in 2010, Hefner had a subspecies of marsh rabbit named after him. The endangered subspecies was on the brink of extinction when Hefner donated $900,000 to save the land the species called home. According to studies, there are less than 300 “playboy bunnies.”

Photo Credit: Frazer Harrison/Getty Images for the Wildlife WayStation
Photo Credit: Frazer Harrison/Getty Images for the Wildlife WayStation

The marsh rabbit was discovered in 1984 and declared endangered in 1990. When land development in Florida threatened to wipe out the species, Hefner stepped up to save the animals. He was given praise in 2010 and the rabbit was renamed in Hefner’s honor.

Playboy Published a Pro-LGBTQ Rights Short Story in 1955

In 1955, Hugh Hefner ran a controversial short story in Playboy about a dystopian future where homosexuality was normal and heterosexuality was outlawed. Readers revolted against Hefner. The progressive story had been rejected by every major publication at the time for good reason.

Photo Credit: Getty Images
Photo Credit: Getty Images

Hefner defended his decision, writing in a defiant note, “if it was wrong to persecute heterosexuals in a homosexual society, then the reverse was wrong, too.” From that moment forward, Hugh Hefner became a vocal proponent of LGBTQ rights, even featuring the already mentioned Caroline Cossey in 1991 pictorial.

Hefner Told The Truth About AIDs When Other Publications Wouldn’t

According to a Hugh Hefner interview from 1994, Playboy began writing about AIDS before anyone else. Hefner made sure his magazine was fair and honest about the disease. He recalls seeing a headline in 1985, “AIDS — Now We Are All At Risk” and being disgusted by it.

Photo Credit: Victor Crawshaw/Mirrorpix/Getty Images
Photo Credit: Victor Crawshaw/Mirrorpix/Getty Images

At the time Playboy was struggling, and Hefner was recovering from a stroke. Taking away some of the glamour from the magazine to tell an important story became a priority. The “sexual revolution” that Hefner fought so hard for was over. His new mission became proper education to fight media-produced hysteria.

The Playboy Mansion Was Put Up For Sale In 2009

In 2009, Hugh Hefner put the Playboy Mansion on the market. To own a piece of American cultural history, Hefner asked for $200 million. Of course, anyone interested in the property would need to follow a few rules. Hugh Hefner would continue to live in the house until his death. His bedroom would be strictly off-limits.

Photo Credit: GABRIEL BOUYS/AFP/Getty Images
Photo Credit: GABRIEL BOUYS/AFP/Getty Images

Hefner sold the mansion in 2016 for half of his asking price. The buyer was Hefner’s neighbor, Daren Metropoulos.

Hugh Hefner Died From An E.coli Infection

When Hugh Hefner died, initial reports indicated cardiac arrest and respiratory failure as the cause. While contributing factors, his death certificate revealed the leading factor was an E.coli and Septicemia infection. The strain of E.coli was highly resistant to antibiotics.

Photo Credit: Paul Harris/Getty Images
Photo Credit: Paul Harris/Getty Images

At the time of his death, Hugh Hefner was still married to Crystal Harris. She, along with Christie Hefner, arranged the funeral and his burial. Where exactly Hefner was buried, however, was not up to them. Hefner bought his burial plot in 1992 in a spot that holds a special place in his heart.

He is Buried Next to Marilyn Monroe

In 1992, Hugh Hefner bought the crypt next to Marilyn Monroe for $75,000. Not only was Monroe the first Playboy cover model, but Hefner also considered her a soldier in the fight for free love. In 2009, Hefner told the Los Angeles Times, “I’m a believer in things symbolic. Spending eternity next to Marilyn is too sweet to pass up.”

Photo Credit: Mel Bouzad/Getty Images
Photo Credit: Mel Bouzad/Getty Images

In reality, Hefner never met Monroe. He paid $500 for already-taken nude photographs when he published his inaugural 1953 issue. The pictures were used without consent and endangered the young star’s career. Now he’ll have an eternity to apologize.