Hugh Hefner married Mildred Williams in June 1949. It’s hard to imagine the magazine mogul—who has admittedly had sex with thousands of women, most of whom are a fraction of his age—marrying his high school sweetheart. But that’s what regular guys did back then, and Hefner was definitely a regular guy by the standards of the time. He became engaged to Millie right before he left for the army and returned to get married, attend college, get a job and have kids. There was almost no deviation from the typical path walked by young men during this postwar period, right down to moving his wife in with his parents after tying the knot. The only hint that Hefner was different was his early fascination with sex—he read everything having to do with sex, from pornographic materials to medical journals to books on sex law, according to Elizabeth Fraterrigo, author of Playboy and the Making of the Good Life in Modern America.

After several stints in the writing world, Hefner landed a job as a copywriter for Esquire while creating his own book of racy cartoons called That Toddlin’ Town: A Rowdy Burlesque of Chicago Manners and Morals. Esquire quickly relocated to New York in 1951, and Hefner stayed behind hoping to start his own magazine. His first attempt was Pulse: The Picture Magazine of Chicago, but the publication never came to fruition due to lack of funds and news of Millie’s pregnancy. Two short years later, with financial help from the bank and his mother, Hefner released the first 44-page issue of Playboy in December 1953.

No one knew the then 27-year-old at the time, and the first issue with Marilyn Monroe on the cover was undated because he didn’t know if there would ever be a second. Inside featured a full nude photo spread of Monroe, who was the first Sweet of the Month (later called Playmate), that Hefner purchased from a local calendar company. The mission of the magazine was made clear by a message Hefner wrote on the first page: “We aren’t a ‘family magazine.’ If you’re somebody’s sister, wife or mother-in-law and picked us up by mistake, please pass us along to the man in your life and get back to your Ladies Home Companion.” “It was mostly a selfish endeavor,” said Fraterrigo. “But part of it was [Hefner’s] attempt at uncovering an interest most American men had at the time. It wasn’t spoken about, but it was there. He wanted to put it out in the open.” It turns out that his doubt was unwarranted—the first issue sold over 50,000 copies at 50 cents each, thus beginning Hefner’s ascent into the lifestyle of the rich and inordinately famous.

There was something in Hefner’s personality that pushed him to become the face of America’s dirty little secret. A dream and merciless pursuit helped him market and sell Playboy, which would have been called Stag Party if copyright issues didn’t get in the way, but Hefner can’t take all the credit. Steven Watts, author of Mr. Playboy: Hugh Hefner and the American Dream, argues that the time in American history is essential to understanding Hefner’s success. The magazine’s release came on the heels of a war and a brutal recession. Americans were picking up the remnants of their old lives while trying to start fresh in an era of newfound peace. “People were more interested in exploring and being adventurous, especially sexually, and Hefner realized he could fill that niche,” Watts said. “He knew he had the right ingredients to make a statement, and he was hoping others would, too.”

The 1950s were also marked by the rise of the feminist and civil rights movements. The majority of popular culture and publications was family-orientated, geared toward a docile group of women at home. Hefner promised something different, a form of entertainment for manly men that they didn’t know they needed. And not just middle-aged husbands, but men all over the spectrum, from ages 18 to 80. Playboy disregarded the sensitivities of the time and tried to go straight to the man’s desires, which weren’t being met by the magazines producing postwar fluff content. “Our Puritan roots are deep,” Hefner told TIME. “We’re fascinated by sex and afraid of it.”

Hefner has come a long way from the days of compiling Playboy on his kitchen table. He’s an 88-year-old bonafide stud, able to slink around in silk pajamas at the Playboy Mansion watching “Where the Sidewalk Ends” with his buddies. He has had three wives and countless girlfriends during his run and now, after designating most business responsibilities to his children and coworkers, he has little to do other than play the part of a lavish host. Although the magazine peaked in 1972 by selling 7 million copies, it still retains a hardcore fan base. Other than the magazine itself, which outlived other publications such as Penthouse, the bunny’s legacy is kept alive through media endeavors and the licensing of consumer products. It’s hard to imagine a world without Playboy, without playmates and parties and the iconic bowtied bunny, but Hefner carved out a place for himself in the industry that will still be difficult to forget.

Whether it was his own drive, the decade in history or more likely a combination of both that boosted Hefner to his level of success—the magazine, Playboy Enterprises, TV shows, etc.,—one thing’s for sure: he’s still got it, and always will.