Hugh Hefner’s life branched sometime in his late teens.

Young Hugh had a crush on a lovely young woman, a perky brunette named Betty. She spurned his affections in favor of another, an act that broke young Hugh’s heart. His response to that event was either an act of moxie and resilience or a life-long plunge into a hedonistic and reductionist view of the world that warped our culture, depending on your point of view.

In the wake of his heartbreak, Hugh transformed himself into “Hef” as he dubbed himself. His new incarnation was self-assured, the life of the party. The creative young boy with the impish grin who wrote and drew comic books and made his own horror movies steadily transformed into a swaggering young publisher with a knowing smirk affixed permanently to his face.

In his early 20s, Hef set out to launch a new magazine for men. The new publication was a reaction to what Hef saw as the repressive sexual culture of the 40s and 50s. It also filled a gap left by men’s publications of the time, which catered to the outdoorsy, sports-minded man’s man. The “Playboy” man was sophisticated, well-versed on the issues of the day, and had a lovely young lady draped on his arm.

The inaugural edition featured a nude photo of Marilyn Monroe, a young actress whose career was beginning to take off. She didn’t pose for the photos specifically for Playboy; the images had been shot sometime before when she was desperate for money. She shot the portraits under an assumed name, and the photographer took the pictures sold them to various publishers, including Hefner. Monroe didn’t even know where they ended up until after they were published.

Hef kept his own name out of the inaugural issue in case it failed. But he leveraged Monroe’s identity to sell copies. Depending on how you view Hef, his choice was either a stroke of editorial genius or pure exploitation. Either way, the results were the same. The issue sold.

Monroe’s images were crucial to Playboy’s strong start and ultimately launched Hefner on the path to making millions. Yet, she was compensated just $50 for the images, paid by the photographer after the original shoot. Hefner and Monroe never met and spoke only briefly on the phone.

The images could have tanked Monroe’s burgeoning career, but they didn’t. They instead cemented her status as a sex symbol. It can be argued that Monroe’s perception as a sex symbol hampered her career, too, limiting her options for roles and ruling her out as a serious actress.

The circumstances around the launch of Playboy illustrate the complexity of Hef’s legacy. He built an empire on what some would argue was the exploitation of young, vulnerable women. Some of those women capitalized on their association with Hef and indeed sought out the opportunity to appear in Playboy as a way of advancing their careers. Some were demoralized and debased by their association with Hef.

Hef was also a vocal proponent of women’s reproductive rights and advocated birth control and abortion rights. Some also credit him with advancing women’s sexual freedom. He is also hailed as a champion of free speech.

But at the bottom of those assertions about Hef’s accomplishments and contributions, there’s this question: who were those efforts designed to benefit? Were they designed to benefit women? Men? Hef himself?

Was Hef a philosopher, earnestly seeking a higher truth and better way for all? Or was he a crass marketer who found a way to capitalize on the basest, most selfish human instincts?

Was he really the party’s self-assured life, fulfilled by a jet-setting life filled with an endless supply of young, beautiful women ready to serve his every need? Or was he really a heartbroken young lad, desperately trying to insulate himself from any risk of ever being rejected again?

The line between moxie and mayhem can be fine, and Hef danced on it. Where do you think he ultimately lands? Was he a hero, or something else?

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