"[Hefner] defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history. He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston and all of us at Playboy Enterprises," Cooper Hefner said in a statement.
Market researcher Wealth-X told Business Insider that at the time of his death, Hefner was worth at least $110 million. While it's not 100% clear who will inherit his wealth, Us Weekly reported in 2013 that Hefner's wealth would be left to "his children, the University of Southern California film school, and a variety of charities."
Playboy announced in October 2015 that it would no longer be featuring nude photos in its pages. By February 2017, however, the magazine said nude photos would be back.
In more recent years, the magazine and brand began to struggle. The New York Times reported in 2009 that the magazine began promising advertisers a 1.5 million circulation, down from the previously promised 2.6 million.
next slide will load in 15 secondsSkip AdSkip AdHe also starred in and produced the E! reality show "The Girls Next Door," along with then-girlfriends Kendra Wilkinson, Bridget Marquardt, and Holly Madison. The show aired from 2005 until 2010.
Throughout the 1990s and 2000s, Hefner made guests appearances on various TV shows.
Hefner had placed his office in his bedroom since the 1960s, but it wasn't until the 1970s, when he moved out to Los Angeles, that the famous silk robe became his signature look.
Hefner had two children with his first wife, Millie Williams, in the 1950s — a daughter, Christie, and a son, David. The couple divorced in 1959, however. In 1989, Hefner married a former Playmate of the Year, Kimberly Conrad. Together, they had sons Marston and Cooper. Hefner and Conrad divorced in 2010, and Hefner married Crystal Harris in 2012.
However, neither Hefner nor his brand ever seemed to lose their youthful flair. In 1980, he was awarded the 1,716th star on the Hollywood Walk of Fame.
next slide will load in 15 secondsSkip AdSkip AdIn 1977, AP reported that Hugh Hefner had said his $200 million dollar empire "is settling down after a flamboyant youth and a tumultuous adolescence."
The following year, Hefner officially moved from Chicago out to California and into the famed Playboy Mansion.
He was active politically, included when he helped to finance the landmark Roe v. Wade decision on abortion in 1973.
During the '70s he also helped produce a few feature films, including Roman Polanski’s "Macbeth."
Hefner traveled in style inside his $5.5 million private Playboy jet in the 1970s. By that time, Playboy had cemented itself as a cultural icon with its famous "Playboy Interviews," which featured subjects like Stanley Kubrick, Dr. Martin Luther King Jr., and Ayn Rand.
next slide will load in 15 secondsSkip AdSkip AdHe also hosted the show "Playboy After Dark," which had various musical performers at guests. Hefner also created the Playboy Club, which had several nightclub locations.
Throughout the 1950s and '60s, Hefner hosted a few TV shows, including "Playboy's Penthouse," during which he would interview celebrities like Sammy Davis Jr. and Bob Newhart.
Hefner launched Playboy magazine in 1953 with $8,000 in borrowed money. Its first issue featured Marilyn Monroe, and it sold 54,000 copies.