Hefner got his start in publishing as a copywriter for Esquire but left the position in January 1952 after he was denied a $5 raise.
He also owned 100 per cent of the magazine itself, the sales of which had declined severely over the years.
He embodied the Playboy lifestyle after leaving his spouse and children.
"In its heyday in the 60s and 70s, Playboy was supportive of mainstream liberal feminist causes", says Carrie Pitzulo, an adjunct history professor at Colorado State University and author of the 2011 book Bachelors and Bunnies: The Sexual Politics of Playboy. He took part in various reality shows, in which he found new girls. "I was very aware of that!" he said with a laugh. They separated in 1998, and Conrad moved into a home next to the Playboy Mansion.
Born in Chicago on April 9, 1926 to conservative Protestant parents, Hefner has said he retreated into movies to escape his affectionless daily life. The fortune does not take into account the $100million sale of the mansion previous year.
From gorgeous women to lovely mansions, Hugh Hefner was all about living the good life.
The clubs' scantily clad waitresses - known as Bunnies - sported bunny ears and strapless corset teddies, with fluffy cottontails pinned to their derrieres.
"The Playboy Mansion is one of the most iconic properties in the world and the crown jewel of Holmby Hills and the platinum triangle", Metropoulos said.
Hefner, who died on Wednesday aged 91, bought the crypt next to hers in 1992, for $75,000 (£55,930). In-depth interviews with historic figures such as Fidel Castro, Martin Luther King Jr., Malcolm X and John Lennon also were featured regularly.
Hugh Hefner, Playboy magazine founder, and Playboy Playmates and girlfriends arrive at the American Film Institute's "AFI Life Achievement Award: A Tribute to Sir Sean Connery" taping in June.