Start of a Revolution
Having scraped together $8,000, Hefner put together the first issue of Playboy at home and it hit newsstands in December 1953. The magazine, which featured an image of Marilyn Monroe, was an instant success and sold over 50,000 copies.
Man of the Decade
Hefner is pictured here in 1965 at the Playboy Mansion in Chicago. By then, Americans everywhere considered the mogul a symbol for the "Good Life" so many aspired to reach.
Hef's Playmates
Hefner was married to Mildred Williams, the mother of his daughter Christie and son David, for 10 years until 1959. During the next four decades, he romanced a number of girlfriends, including a nine-year relationship with singer and model Barbi Benton. She's pictured here during a 1969 visit to the Playboy Clubs in London.
Growing Business
By 1971, Playboy was selling 7 million copies a month and three years later he moved permanently to his Playboy Mansion in L.A. Additionally, his empire had grown to expand 23 Playboy Clubs, resorts, hotels and casinos with more than 900,000 members worldwide.
Icons Meeting Icons
In 1982, Hefner and Carrie Fisher made a cameo appearance on the Laverne & Shirley show.
The Ups and Downs
At the age of 59, Hefner suffered a minor stroke. In an attempt to slow down his lifestyle, he gave control Playboy Enterprises to Christie and focused more on philanthropic endeavors. In 1989 he married longtime girlfriend Kimberley Conrad. They had two sons together, Marston and Cooper.
Mwah
Hefner continued to remain the face of Playboy well into the turn of the 29th century. Here he is pictured here at the 1999 Cannes Film Festival with a number of Playmates.
Girls Next Door
Hef and his wife Kimberley didn't officially divorce until 2010, but they had an open relationship for years—most publicly when Hefner starred from 2005 to 2010 on E!'s The Girls Next Door with resident girlfriends Kendra Wilkinson, Bridget Marquardt and Holly Madison.
Newlyweds
Hefner married Crystal Harris on Dec. 31, 2012 during a lavish ceremony at the Playboy Mansion. Their age difference captivated headlines, and they continued to celebrate milestones together over the years.
Gone Too Soon
Hefner's brother Keith Hefner passed away in April 2016. The longtime Playboy executive was not only a fixture at the Playboy Mansion, but he also had roles in several films like Star 80, Fever Pitch and Evil Town.
Following in Dad's Footsteps
Son Cooper, who was named the magazine's Chief Creative Officer, addressed his father's failing health in April 2016: "I think because he has stepped back from the day to day operations of the business, people have thought that his health was not very good. The reality is he has a really bad back—that happens when you're 90—and he is enjoying life at the mansion."
Later Years
As the editor-in-chief of Playboy magazine continued to lead a more private life, fans were delighted to see a family photo appear on his Twitter timeline in November 2016.
End of an Era
Hefner passed away at the age of 91 from natural causes. According to a press release, he died at the Playboy Mansion surrounded by loved ones.