Magazine mogul Hugh Hefner was romantically involved with some of the most beautiful women on the planet. However, he revealed something before his death that will make you think differently about the entrepreneur’s personal life…

Few people in American entertainment are more iconic than Hugh Hefner. He was a suave businessman, a media mogul and a publishing entrepreneur. Hefner remained in the spotlight for the better part of a century through his various enterprises – most notably with the men’s magazine Playboy. And having shot to fame and revolutionized the industry, he supposedly slept with more than 1,000 women. However, there was one secret about his life that he revealed before his passing in September that is sure to leave you gobsmacked…

From humble beginnings in Chicago, Illinois, Hugh Hefner became a stand-out figure in the history of U.S. entertainment. As the creator and founder of Playboy, Hefner was a prominent persona in pop culture for more than half a century. However, his success didn’t just fall into his lap.

After a stint in the army, as well as some valuable years spent in the publishing industry, Hefner felt there was a gap in the market for a high-class men’s magazine. He envisaged a publication that would walk a fine line between informing, entertaining and, most notably, titillating.

Raising money from the bank and from those closest to him, Hefner set about putting together the now infamous magazine in the fall of 1953. In December of that year, the first issue of Playboy went on sale. With its unique brand of adult content, humor and fiction, the magazine proved to be a hit.

In the decades that followed, Playboy became a cultural staple. Now encompassing the Playboy Mansion and various other offshoots of the magazine, the business has faced trials and tribulations and has come under attack from advocacy organizations and religious groups for its sexualized representation of women.

Image: FREDERIC J. BROWN/AFP/Getty Images

And while many celebrities have been interviewed for the publication, many have also appeared as nude centerfolds over the years. The likes of Marilyn Monroe, Ursula Andress, Nancy Sinatra, Farah Fawcett have graced its pages to the dismay of some sections of the public.

But it wasn’t just professionally that Hefner ruffled feathers. He also did in his personal life. And after the devastating break-up of his first marriage in 1958, Hefner reinvented himself – choosing to surround himself with Playmates from his own magazine.

This radical change lasted for well over two decades, garnering Hefner a reputation as a party animal and a promiscuous entertainer. However, after suffering from a minor stroke in 1985, he changed his lifestyle, as well as his public persona.

Taking a backseat after the health scare, Hefner decided to hand the reigns of the company over to his daughter Christie Hefner in 1988. With a more stress-free regimen, he decided it was time to settle down and marry again. So he wed former Playmate of the Year Kimberly Conrad in 1989.

It wasn’t long before his family expanded, with children Marston Glenn and Cooper Bradford born soon after their wedding. However, after the marriage fell apart ten years later, Hefner returned to his old ways – famously having several girlfriends at one time.

His third and final marriage in 2012 to model Crystal Harris marked the final attempt at love for the aging entrepreneur. But Hefner passed away just last month at the age of 91. What he said regarding his love life before his passing is sure to raise a few eyebrows…

Despite claiming to have been intimate with more than a thousand women in his lifetime, Hefner said before his death that he never found the one. The revelation comes by way of an interview with The New York Times. He said, “I’ve spent so much of my life looking for love in all the wrong places. I never really found my soulmate.”

It’s certainly a surprising statement given the amount of time he spent in the company of various woman. But he did address that point in a 2013 interview for Esquire. He said, “There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn’t married. You have to keep your hand in.”

Image: Charley Gallay/Getty Images for Playboy

Clearly, Hefner was distraught towards the end that he never managed to find true love. However, his widow Crystal Harris certainly seemed to have given him more hope in his later years. He said in the same interview for Esquire, “I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last.”

He went on, “All our friends think it’s made in heaven. It’s only people who don’t know us, who simply see us as stereotypes in terms of age and beauty,” before adding, “I want the rest of my life to be very much like it is now. I want it to be like this.”

Image: FREDERIC J. BROWN/AFP/Getty Images

After he passed, Harris broke her silence on what her husband meant to her and the rest of the world, recently telling People magazine, “He was an American hero. A pioneer. A kind and humble soul who opened up his life and home to the world.”

Image: Alberto E. Rodriguez/Getty Images

She also said, “I felt how much he loved me. I loved him so much. I am so grateful. He gave me life. He gave me direction. He taught me kindness. I will feel eternally grateful to have been by his side, holding his hand, and telling him how much I love him.”

Image: Christopher Polk/Getty Images for Playboy

His son Cooper also paid tribute to Hefner, “My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom.”

Image: Christopher Polk/Getty Images for Hugh M. Hefner Foundation

And he went on to say, “He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history. He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston and all of us at Playboy Enterprises.”

Image: Charley Gallay/Getty Images for Playboy

However, Harris herself topped that, telling People magazine, “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. There never has and never will be another Hugh M. Hefner.”

Despite never finding his soulmate, Hugh Hefner did find fame and fortune through his own foresight and ambition. Whatever you think about the way he lived his life, the impact he’s had on modern pop culture can’t be denied– even without the true love of a woman.