He was a prominent American businessman, magazine publisher, and playboy who founded and served as the editor-in-chief of Playboy magazine in 1953. In addition, he held the position of chief creative officer at Playboy Enterprises, the company that publishes the magazine. Along with advocating for sexual liberation and freedom of expression, Hefner also devoted himself to various political and philanthropic causes. He actively participated in public issues as an activist.
Affectionately known as 'Hef', Hugh possessed an IQ of 152, putting him in the category of genius. It is therefore no surprise that he earned his degree in a mere two-and-a-half years, rather than the usual four-year period in the United States. At the University of Illinois at Urbana-Champaign, the Playboy founder majored in psychology. Although he studied for just one semester towards an MA degree, he managed to complete a research paper titled "Sex Behavior in the U.S. Law", for which he received an A-grade. Additionally, it is interesting to note that Hefner is a distant cousin of both John Kerry and George W. Bush.
Prior to establishing a multi-million dollar empire centered around the objectification of women, Hefner had served in World War II and worked in various positions within the publishing industry. He tried his hand at cartooning and also worked as a copywriter for Esquire. Notably, Hefner had also served as the circulation director for a children's magazine based in Chicago.
In 1953, he established Playboy magazine, starting with a $600 loan secured against his furniture and investments from family members. Hefner's original choice of name for the magazine was "Stag Party". However, he opted for the name "Playboy" and featured a nude photograph of Marilyn Monroe in its debut issue. With an initial investment of just $8,000, the magazine quickly gained widespread attention and became one of the most iconic publishing empires in history.
During his college years, Hefner frequented Bunny's Tavern, a bar and restaurant known for waitresses dressed in bunny outfits. In 1960, he established his first Playboy Club in Chicago, where the waitresses also donned bunny costumes while serving customers. The success of the club led to the opening of several more clubs, including locations as far-reaching as Japan and Jamaica. The clubs became renowned for showcasing some of the most popular entertainers of the time, including Sammy Davis Jr. and Sonny & Cher. However, escalating costs led to the gradual closure of the clubs, beginning in the late 1980s.
Hefner resided in the renowned Playboy mansion under peculiar circumstances - he never actually owned it outright. Instead, it was technically owned by Playboy Enterprises, which leased it to him for a mere $100 per year.
When I got the Playboy Mansion I didn't leave the property for months, to shop or to go anywhere.
In 2016, the neighboring property of the estate purchased it for $100 million. However, Hefner was unwilling to relocate, and instead opted to pay an annual rent of $1 million to remain at the mansion, albeit for only about a year.
Hefner has been married thrice, and consistently maintains several girlfriends around him. From his first two marriages, he has fathered four children. Hefner claimed that he reserved himself for his first wife, Mildred Williams. However, following their sexual encounter in 1949, when he was 22 years old, Mildred disclosed that she had been unfaithful to him before their wedding while he was serving in the army.
That was the most devastating moment in my life.
Prior to his death, Hefner claimed to have had sexual encounters with over 1,000 women.
In the late 1960s, Hefner began sporting his now-iconic smoking jacket look. As Playboy continued to grow in success, Hefner relocated his office to his bedroom for convenience. It was during this time that he discovered he could wear his smoking jacket throughout the day.
I started wearing them all the time because I was working at night, and then I started wearing them when I entertained.
According to the New York Times, Hefner allegedly possessed over 200 personalized smoking jackets and pajamas, and he did not wear any undergarments beneath them.
He has achieved two Guinness World Records, one for the longest tenure as Editor-in-Chief and another for having the largest collection of personal scrapbooks. His scrapbooks consist of pictures collected from his work at Playboy magazine and from his time spent with friends at the mansion.
It was probably just a way of creating a world of my own to share with my friends. And in retrospect, in thinking about it, it's not a whole lot different than creating the magazine.
He purchased a mausoleum drawer next to Marilyn Monroe in 1992 for $75,000, intending to be buried there himself.