Hugh Hefner, the ultimate playboy who frolicked through life long enough to become an icon in his own time, died Wednesday night at the age of 91.

Playboy Enterprises announced Hefner's death on Twitter at 8:13 p.m. PT and released a statement saying Hefner died at his home of natural causes surrounded by family.

Shortly after, Hefner's son Cooper released a statement recalling his father's "exceptional and impactful life as a media and cultural pioneer."

Even in death, Hef retains his rakish savoir faire: In 1992, he paid $75,000 to obtain the vault next to Marilyn Monroe, thereby ensuring he could spend eternity with Playboy’s first cover girl.

Hugh Marston Hefner was the unlikeliest of skin-trade revolutionaries. Raised in Chicago under the watchful eyes of conservative parents, a hormonal Hefner quickly found that his average looks could be overcome by a burgeoning talent for cartooning and an innate desire to challenge buttoned-down 1950s conventions.

Hefner first learned his way around a magazine as a copywriter for Esquire. But when he was denied a raise there, he sold what little furniture he had and laid the foundation for a publishing empire.

In 1953, a time when states could legally ban contraceptives, when the word "pregnant" was not allowed on I Love Lucy, Hefner published the first issue of Playboy, featuring naked photos of Marilyn Monroe and an editorial promise of "humor, sophistication and spice." The Great Depression and World War II were over and America was ready to get undressed.

Success came fast and furious for the fledgling publisher, who was both tapping into and fueling the counter-culture bonfire that raged throughout the 1960s. His Chicago mansion became a hub of outrageous activity, a Parisian salon set in a Roman bathhouse.

Although during this period Hefner drew his share of fire from women and men alike (charging he was sexist and amoral), these would prove Hefner’s glory years, says Steven Watts, author of Mr. Playboy: Hugh Hefner and the American Dream.

“People tend to forget about how truly unique he was in those early days,” says Watts, whose 500-page biography paints the portrait of a driven man willing to stop at nothing in order to achieve his vision. “He really was a huge cultural figure.”

His accomplishments range from the salacious to the significant.

In the former camp: incessant couplings with staffers and Playmates alike, most of whom saw the workaholic dressed in his favorite day and night wear, pajamas.

In the latter: weighty magazine interviews and features on leading cultural thinkers and the integration of his Playboy Clubs at a time when racial tensions were searing.

Beyond helping nudity go mainstream, Hefner also ushered in upscale consumerism with gadget reviews that would anticipate by decades magazines such as Gear. “The lesser known fact is that Hefner was as responsible for the consumer revolution as he was the sexual revolution,” says Watts.

Ever atune to image, Hefner traded his native midwest for Los Angeles just as his fame was taking off (in a massive private jet emblazoned with the bunny logo). He bought a Holmby Hills mansion in 1971 for the then outrageous sum of $1 million. By design, the one-time cartoonist was on his way to becoming a caricature.

Though no longer needing to work day and night, Hefner was never seen without his pipe and PJs. Both his round bed and his infamous backyard grotto were filled with an endless parade of women, some of whom stayed (Barbi Benton, Carrie Leigh) while most vanished (as had his first wife Millie, with whom he’d had two children, David and Christie).

The mansion became a second home for famous friends, ranging from legends such as Frank Sinatra to whoever was hot in Hollywood at that moment. His parties were infamous, costumed affairs that left little to the X-rated imagination. And then, somewhat abruptly, they went PG.

After a stroke in 1985 at age 59, Hefner throttled back on his raucous lifestyle and a few years later handed over the reins of his empire to daughter Christie. In 1989, the dedicated bachelor shocked the world by marrying Playmate Kimberly Conrad. The couple soon had two sons, Marston (1990) and Glenn (1991); the driveway signs at the mansion quickly changed from “Playmates at Play” to “Children at Play.”

But this detour into traditional family life was not to last. The pair divorced in 1998, with Conrad taking a house nearby and her sons free to wander between their parents’ homes.

Though proud of his eight years of fidelity, Hefner seemed happy at his new lease on the wild life. He also was convinced that his second marriage had hurt his reputation as a swinger and had even led to his company’s financial struggles.

“I’d been off the scene for eight and a half years,” he told USA TODAY in 2005. “When that (marriage) didn’t work in the beginning of 1998, I came back as a bachelor. I think a whole generation had been waiting for me to come out and play.”

He wasted little time. Though in his 70s, Hefner began dating several girls at once, often making the rounds of Hollywood clubs with a harem of blondes.

His E! reality show, The Girls Next Door, only fueled his reputation as a ladies man. Although he had once before considered then rejected a Hollywood movie on his life (he felt the Tony Curtis vehicle wasn’t treated his life seriously), Hefner started to collaborate with producer Brian Grazer on a screenplay about his life.

He was hopeful someone “boyish” would play him. “Johhny Depp is certainly a possibility,” he said.

Depp would seem a good choice. Having already played one outrageous and iconic writer to crazed perfection (Hunter S. Thompson), the actor could handle a taboo-shattering bon vivant who only took yes for an answer.

Playboy published its first non-nude issue in March 2016 and before that had launched a safe-for-work Playboy Now app.

Cooper Hefner announced in February that after one buttoned-up year, Playboy was bringing nude photographs back to its magazine.

"I'll be the first to admit that the way in which the magazine portrayed nudity was dated, but removing it entirely was a mistake," he said.

Also back for a new generation: the Party Jokes section and The Playboy Philosophy, a political and cultural column written by Hefner, nearly 40 years after his father last wrote it for the magazine.

Hefner spent his last years ensconced in the faux-gothic splendor of his Mansion, despite the fact that it sold In August 2016 to Daren Metropoulos, 33, the co-owner of Twinkies maker Hostess.

Metropoulos lived next door to the Playboy mansion since 2009, and agree to buy it with the condition that Hef could remain there to finish out the party that was his quintessentially American life.

Contributing: William Keck, Mike Snider and The Associated Press.