Hugh Hefner, the founder of the iconic Playboy magazine and brand is dead at 91.

Hefner was born to Methodist parents who had moved from Nebraska to Chicago and raised their son in a strict and socially conservative household.

Those early days growing up “with a lot of repression,” as Hefner said in interviews laid the groundwork for his rebellion.

At the University of Illinois, Hefner took up drawing crude and racey drawing cartoons. He started Playboy in 1953 as a home for his lewd cartoons. But the magazine would quickly grow beyond Hef’s drawings, embodying a new ideal for the American man.

Hefner wrote in the first issue of Playboy,

“We enjoy mixing up cocktails and an hors d’oeuvre or two, putting a little mood music on the phonograph and inviting in a female acquaintance for a quiet discussion on Picasso, Nietzsche, jazz, sex.”

This was the Playboy philosophy. In an age of sexual repression, social conservatism, and prudishness, Hefner sought to liberate America’s strict attitudes.

And while he accomplished this by publishing pictures of scantily-clad women in bunny costumes, he also fought important battles for the civil rights movement and was an early advocate for marijuana legalization.

Hefner’s legacy is complicated by the opposing ideals of sexual liberation, civil rights activism, and male chauvinism. Playboy was simultaneously peak high brow (there were truly groundbreaking interviews with cultural figures like Muhammad Ali and Miles Davis) and peak low brow.

Hefner came under fire from feminists for his objectification of women. Gloria Steinem famously went ‘undercover’ as a Playboy bunny and published a hit piece on Hefner and Playboy for Show magazine.

Hefner failed to understand the feminist critiques of Playboy, he saw himself as liberating American sexuality in a time when puritanical ideals still ran rampant through society and mass culture.

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And for all of the feminist criticism of Hefner, most of which is legitimate, perhaps more importantly he liberated America’s attitudes towards race. Hefner hosted music stars like Nat King Cole and Ella Fitzgerald on the premier of his nighttime show Playboy’s Penthouse in 1959 at a time when large swaths of the country still had Jim Crow laws.

In its early years, Playboy’s detractors were equally concerned with the magazine’s endorsement of Black American culture as much as the pictures of naked women. Hefner gave young Black writers like Alex Haley a start, in fact the first ever interview Playboy published was Haley’s interview of Miles Davis.

Keli Goff wrote in the Daily Beast of Davis’ interview and of the Black American presence in Playboy,

“In the interview, Davis discussed his thoughts on racial inequality, setting the tone for what would become a staple of the magazine: serious people giving serious interviews, on serious subjects, including many prominent people of color. Those people included everyone from athlete and activist Muhammad Ali to Sammy Davis Jr., and Dr. King, who granted the longest print interview of his career to Haley for Playboy.”

Martin Luther King Jr.’s longest ever print interview was for Playboy, that’s quite the fact.

In many ways Hefner can be credited with the normalization of Black Americans in popular (white) cultural spaces. People who didn’t know about Malcolm X but wanted to see pictures of Playboy bunnies were then exposed to things they’d never seen before.

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But Hefner also offered tangible assistance to the civil rights movement. When three young civil rights workers were murdered in Mississippi, Hefner quietly gave money to the cause to find their killers.

The great comedian and civil rights leader Dick Gregory, who died last month, told British GQ in 2011 about Hefner’s help,

“I called Hugh Hefner. I asked him to deposit $25,000 in my account, so I could put that up as a reward. The next day the FBI put up $30,000. Hefner understood what those rednecks didn’t: that things had changed. That you could no longer argue that you’d ‘killed three Jews’. Or ‘killed three blacks’. What you’d done was, you’d killed three fellow human beings.”

Hugh Hefner leaves behind a great and complicated legacy. In many ways he deserves credit for the liberation of America’s social and sexual repression.

In other ways his depiction of women remains truly problematic. But mostly, Hefner was a trailblazer of progressivism at a time when America needed it most.

Rest in peace, Hef.