By Howard T. Brody

In December 1953, a University of Illinois psychology graduate living in Chicago – who had previously worked in publishing as a promotional copywriter for Esquire magazine, a circulation promotions manager for Children’s Activities magazine and who handled sales and marketing for Publisher’s Development Corporation – launched a publication that would forever change the landscape of American pop culture and help usher in the Sexual Revolution of the 1960s.

Raising $8,000 by selling his furniture and borrowing from 45 investors (mostly family and friends), Hugh M. Hefner introduced the world to Playboy and the world, in turn, was introduced to Hef.

That first issue was not exactly easy to distribute. It was at a time when obscenity laws in the U.S. were still very much stringent across the country and while having a photograph of Marilyn Monroe on the cover was not a big thing, having a nude photo of her inside the magazine was. As a result, there was pushback at every turn, but Hef stuck to his guns and his fortitudinous paid off. That issue, which had no cover date because Hef didn’t know if he could produce a second issue, sold more than 53,000 copies and gave life to a whole new industry.

If not for Hef’s determination, the multitude of magazines that followed Playboy into the marketplace after obscenity laws fell, Penthouse and Hustler among them, simply would not exist. This especially holds true for STRIPLV, as publisher Scott Santos’ creativity was very much influenced by the Playboy style, which of course had Hefner’s DNA ingrained in every aspect of the publication.

But Hef was more than just Playboy’s publisher and editor; he was its iconic figure who lived up to his reputation as an advocate of sexual liberation, freedom of speech and expression, political activism, philanthropy and of course, living the lifestyle of a playboy.

During its heyday, Playboy used to have an ad in every issue that asked: “What sort of a man reads Playboy?” While the answers were always different and sometimes tied to a product or service that was being advertised in that particular issue, they all painted a picture of a certain type of individual. Whether the man in the ad was well-dressed and well-groomed, well-traveled or simply a man of substance who had an eye for style, at the very root of the message Playboy was describing Hef and subconsciously they were telling us that if we followed the magazine’s blueprint, we could be like him. And we believed them.

Within a year of its first issue, Playboy’s circulation was about 200,000. By 1960 they had 1 million subscribers and at its height in 1972, Playboy magazine had a circulation of 7.2 million. Today, in the age of magazine subscription decline, circulation is down to 579,000.

Hef was certainly a trendsetter. A decade after he published his first issue, he moved his office from Playboy’s North Lake Shore Drive corporate address to the original Playboy Mansion – which was a 70-room, 30,000 square foot classical French brick and limestone residence, built in 1899 on North State Parkway in Chicago’s Gold Coast district – and traded in his business suits for silk pajamas.

In what would become his unique iconic style, during his work days Hef wore a color that he called “gunfighter black,” and at night he would wear rich colors like red, green or blue. In the evenings he would add a bathrobe, and when company came over he’d slip on a smoking jacket; after all, he had to accessorize his then ever-present pipe.

While Playboy’s ideal bachelor was an affluent white man, change was afoot. In 1960, Hef began opening a string of clubs around the world where waitresses wore revealing outfits that included bunny ears and fluffy white tails. The clubs influenced and impacted the cultural landscape of the time as they gave early breaks to entertainers such as Rich Little, Mark Russell and George Carlin. And although feminist Gloria Steinem took Hef to task in a story she wrote for Show magazine where she disparaged the clubs and the people who worked there; his Playboy Clubs provided a venue in which racial integration was endorsed as this was a subject he was personally dedicated to. His first job in a personnel department had involved identifying and rejecting “Jews, Negroes, and guys with long, foreign names,” which was an assignment he found repulsive. His clubs provided a setting for black entertainers to cross the color line, often helping them get their start. Among some of the first African-American entertainers to perform there were comedians Bill Cosby, Redd Foxx and Dick Gregory. Even though a new Playboy Club opened up in Las Vegas at the Palm Hotel and Casino, the last of the original clubs closed its doors in 1988, when Hefner considered them “too tame for the times” and “passé.”

Additionally, while people of color were largely absent from the magazine’s early issues, Hef’s late-night television programs, Playboy’s Penthouse (1959 – 1961) and Playboy After Dark (1969 – 1970), offered a racially integrated cocktail party atmosphere.  While this often meant that black entertainers like Ray Charles, Nat King Cole, Sammy Davis Jr., Ella Fitzgerald and Sara Vaughn would appear on the show performing for and socializing with predominantly white guests, occasionally couples of color joined the party, mingling in the background. In at least one episode Hugh Heffner stepped up and discussed racial integration. The interracial mixing kept the show from being syndicated in the still-segregated South.

In addition to being at the forefront of racial equality, Hef was a strong proponent of the First Amendment and contended that the magazine contained far more substance than just nude photos and centerfolds. Under Hef’s charge, Playboy serialized Ray Bradbury’s “Fahrenheit 451,″ several James Bond novels by Ian Fleming and published works from such noted authors as Margaret Atwood, Alex Haley, Joseph Heller, Jack Kerouac, Doris Lessing, Norman Mailer, Gabriel García Márquez, Haruki Murakami, Vladimir Nabokov, John Updike and Kurt Vonnegut.

Under Hef’s direction, Playboy also introduced us to the long-form interview. Each month, an in-depth and unabashed Q&A took place with the celebrities and newsmakers of the day. From Fidel Castro and Malcolm X to Dr. Martin Luther King Jr. and George Lincoln Rockwell, from Miles Davis and Frank Sinatra to Bill Gates and Steve Jobs, they all had their turn in the hot seat. Two of the more memorable interviews included one in the November 1976 issue with then-presidential candidate Jimmy Carter, who revealed that he had “committed adultery” in his heart, and one in the January 1981 issue with John Lennon who gave his interview not long before he was gunned down in December 1980.

As the magazine’s head honcho, Hef had his finger on the pulse of a generation.

While Hef pretty much stayed in Chicago throughout the ‘60s, leaving the city only a handful of times, a major shift took place in 1971 when he bought the mansion in Los Angeles. Hef began flying back-and-forth between L.A. and Chicago on a private DC-9 he nicknamed “The Big Bunny,” which included a giant Playboy bunny decorated on its tail. By 1974, Hef fully transitioned to California, and for decades he was the center of a continuous nonstop party with Playboy models and celebrities. By Hef’s own account, he lived the playboy lifestyle, claiming he had sex with more than 1,000 women, including many of whom appeared in his magazine.

When the Los Angeles Playboy Mansion was put up for sale in 2016 at a whopping $200 million, it included a provision that Hef be allowed to remain in residence for the remainder of his life. In August 2016, Daren Metropoulos, the son of billionaire investor C. Dean Metropoulos and principal at the investment firm Metropoulos & Co., bought the iconic Holmby Hills residence for $100 million, the largest home sale ever recorded in Los Angeles County. The sale allowed Hefner to stay at the mansion until his death in September 2017 as Playboy Enterprises reportedly paid $1 million a year to lease the property back.

Looking back at the life and lifestyle Hugh M. Hefner had, if he were standing in front of us right now we’d have to say “thank you” for never backing down from a First Amendment fight; “thank you” for battling the ignorance of racism; “thank you” for being the trailblazer you were in opening the door for adult publications; and “thank you” for making it cool to work from home in a pair of silk pajamas.

Rest In Peace, Hef; you certainly earned it.

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