The 1992 documentary Hugh Hefner: Once Upon a Time was aptly titled. For generations of men, Hefner—who died September 27 at the age of 91, according to Playboy—lived a fairy-tale existence. As Kiss frontman Gene Simmons bluntly put it in the 2009 documentary Hugh Hefner: Playboy, Activist, and Rebel: “Show me any guy of any age anywhere in the world . . . that wouldn’t give his left nut to be Hugh Hefner at 20, at 50, at 80.”

Hefner, who died of natural causes at his home—the Playboy mansion—in Los Angeles, could not have imagined that Playboy, the magazine he created in his Chicago apartment in 1953 for $8,000, and its bunny logo would “become a fixture of the cultural landscape as universal as Disneyland and Coca-Cola,” as he wrote in 1989, for the magazine’s 35th anniversary issue. Its historic first issue, featuring a centerfold of a naked, pre-stardom Marilyn Monroe, was undated because Hefner wasn’t sure there would be a second. That issue sold almost 54,000 copies at 50 cents each.

Playboy (original proposed title: Stag Party) was a men’s magazine that challenged puritanical convention, focusing more on indoor pursuits than outdoors. “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,” Hefner wrote in the inaugural issue. At its 1975 peak, circulation climbed to 5.6 million.

His auteurist vision made the Playboy lifestyle aspirational (“What kind of man reads Playboy?” was the magazine’s signature marketing slogan), and he transformed himself into the public face of the brand. He hosted two late-night television variety shows, Playboy’s Penthouse, which started in 1959 and ran for 44 episodes, and Playboy After Dark, which ran for 52 episodes between 1969 and 1970. Viewers were guests at a swinging party in Hef’s pad, where Sammy Davis, Jr., Lenny Bruce, or the Grateful Dead might pop in.

A dashing, erudite figure often pictured at work and play at the Playboy mansion smoking a pipe and clad in silk pajamas, Hefner established himself as the embodiment of his “Playboy Philosophy,” which preached personal liberation and championed social causes, including civil rights and gay rights.

Hefner himself, though, was a contradictory figure. He considered himself a feminist, but many accused him and the magazine of objectifying women. Sometimes, Hefner agreed: “They are objects!” he insisted to Vanity Fair in 2010.

As Roger Ebert noted in a 2010 essay, “He has possibly experienced more orgasms with more different women than any other man who has ever lived.” But Hefner also considered himself a romantic.

He championed in Playboy’s pages such cutting-edge authors as Norman Mailer, Jack Kerouac, Ray Bradbury, and Kurt Vonnegut, and featured the most iconic and iconoclastic voices of their times in Playboy interviews, which along with the centerfolds were the magazine’s signature feature. (You know, for those who read it for the articles.) But Hefner also had a nostalgic bent, and immersed himself in the movies and jazz music of his youth.

Hefner was born on April 9, 1926, in Chicago, to undemonstrative Methodist parents. “I was in a home in which I was not getting hugged,” he wrote in Hugh Hefner: Playboy, Activist, Rebel. But his mother was also one of his investors for his fledgling magazine, because, he told interviewers, she believed in him.

Hefner was an average student, but possessed a reported genius I.Q. of 152. He distinguished himself in high school by starting a school paper, serving as president of the student council, and drawing cartoons. After serving two years in the U.S. Army, he took classes at the Art Institute of Chicago before attending the University of Illinois, where he edited the campus humor magazine (and introduced a feature, Coed of the Month). For a graduate course he took at Northwestern University, he wrote a paper about sex laws in the United States.