Rest in peace, Mr. Playboy.

Hugh Marston Hefner, the maverick founder of Playboy magazine, died on Wednesday in California at the age of 91. Once the very public face of the American sexual revolution, Hefner had largely retreated from the public eye to his beloved Playboy Mansion in recent years, where he held regular movie nights with the help of a hearing aid. “It’s tough to watch him struggle, but I’m just happy it’s physical and not mental,” Cooper Hefner, Hugh’s 25-year-old son and Playboy Enterprises chief creative officer, told the Hollywood Reporter earlier this summer.

His father had long divided public opinion in this country. Many men in the baby boomer generation remember Hefner as the ageless sophisticate he presented himself as for much of the second half of the twentieth century—a man immersed in “Picasso, Nietzsche, jazz, sex,” as he wrote in the inaugural 1953 issue of Playboy. Some feminists however, saw him as someone who disrespected women and in his later years, as a somewhat pathetic, Viagra-using, pajama-wearing Howard Hughes recluse. On the political right, he was also viewed as an evangelist of ill morals with his magazine, which at its peak had a circulation of 7 million.

Despite all this, Playboy still retains a firm hold on popular culture. While the internet and the easy availability to pornography means the magazine is a shell of its glory days, it caused a major stir in the media industry when a decision—swiftly reversed—was taken to remove nudity from the magazine. Playboy Enterprises makes a significant chunk of its money selling Bunny-branded apparel in Asia, where the magazine has never been popular, and a Playboy Club is set to open in New York later this year. Earlier this year, Amazon released “American Playboy: The Hugh Hefner Story,” an original docuseries which interspersed interview with the Hefners with dramatized scenes played by actors.

Here are three reasons why Hef’s story still resonates.

1. America is still a puritan society. “Every time you mention nudity in this country, people turn,” says Samir “Mr. Magazine” Husni, director of the Magazine Innovation Center at the University of Mississippi. “You go to Europe and you see nudity on the covers of even political magazines, and it’s not a big deal. But we’ve been a puritan country since the days of Hugh Hefner and when they took the nudity out of the magazine and put it back in, there was buzz.”

2. Playboy was at the forefront of issues that still divide. For decades, the magazine had advocated for reproductive rights and equality for gay people. When the American South was still under the hammer of Jim Crow, Hefner insisted on desegregation at his Playboy Clubs and among guests on his television program—even though he initially took a hit when stations in the South refused to carry it. Though feminists like Gloria Steinem—who famously went undercover as a Playboy Bunny for a magazine story—reviled him, other women leapt to Hef’s defense, noting that their financial freedom was due to lucrative compensation offered by Playboy Enterprises. He named his daughter, Christie, CEO of his company at a time when women leaders were rare in Corporate America. “Just as with Helen Gurley Brown [of Cosmopolitan magazine] on the women’s side, Hefner did it on the men’s side,” says Husni. “For folks who believed, he was the force that lit the candle.”

3. It’s a fun story of hustle and reward—long before #entrepreneurlife was a trending hashtag.  After quitting a drudgery-filled gig at Esquire, Hefner launched Playboy out of his Chicago apartment in 1953 with the help of $1,000 from his mother. Even with all the headwinds facing the magazine industry today, some still value Playboy at around $500 million. Additionally, like his counterpart Jann Wenner at Rolling Stone, Hefner was a rare editor-owner, who hobnobbed with celebs and lived the life he pushed in his pages. “When the first issue of Playboy came out, it did not have a date because he did not know if there would be a second issue,” says Husni. “That’s the beauty of entrepreneurs. It’s a fun, entrepreneurial story and all the baby boomer [men] fantasized about being like Hefner.”