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How much is Hugh Hefner's Playboy empire actually worth?

Hugh Hefner posing during Playboy’s 60th Anniversary special event in Los Angeles, California in 2014 (AFP Photo/Charley Gallay)
Hugh Hefner posing during Playboy’s 60th Anniversary special event in Los Angeles, California in 2014 (AFP Photo/Charley Gallay)

If ever the phrase “sex sells” applied to anyone, then Playboy founder Hugh Hefner was it.

The flamboyant showman has died aged 91 leaving a personal fortune worth about $55 million – but his widow will apparently not see a cent.

According to widely circulated reports, Crystal Harris signed a prenuptial contract before their marriage in 2012 signing away any claim on Hef’s fortune.

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It’s believed his four children from two previous marriages will be the chief beneficiaries of the fortune.

Playmate Jaime Faith Edmondson celebrates the release of Playboy magazine’s “The Freedom Issue” in June 2016 (Rich Polk/Getty Images for Playboy)
Playmate Jaime Faith Edmondson celebrates the release of Playboy magazine’s “The Freedom Issue” in June 2016 (Rich Polk/Getty Images for Playboy)

How did he make his money?
Hefner, born in Chicago, the son of two teachers, launched Playboy in the early 1950s after pulling together $8,000 in loans from friends, family and the bank, adding about $600 of his own money.

The first issue of the iconic magazine hit the stands in December 1953, selling about 50,000 copies. It featured Marilyn Monroe – and he will be buried next to her.

By 1971, Playboy was at its peak, shifting 7 million copies every month, and Hefner was reportedly making $12m a year. By the mid-70s, the Playboy empire was reportedly worth $200m.

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The Playboy Mansion parties were legend, attracting the rich and famous (and infamous) to be entertained by the Playboy Bunnies.

He took the company public and Hugh divided his time between the Playboy mansion in Los Angeles and another mansion in Chicago.

The first issue of Playboy featured Marilyn Monroe (AFP/Frederic J. Brown)
The first issue of Playboy featured Marilyn Monroe (AFP/Frederic J. Brown)

He used a customised luxury DC-30 jet, complete with disco, bar and a large circular bed, to take the Playboy brand around the world.

But more enlightened times saw accusations of exploiting women hit the brand hard. The rise of the internet and freely available online porn sites also bit into sales of the magazine.

Why pay for still images of scantily-clad women when you can see moving images online and often for free?

The Playboy Mansion, bought for about $1.1m in 1971, was sold by Hefner in 2016 for $100m (Charley Gallay/Getty Images for Playboy)
The Playboy Mansion, bought for about $1.1m in 1971, was sold by Hefner in 2016 for $100m (Charley Gallay/Getty Images for Playboy)

How much was he worth in later life?
Hefner handed over control of Playboy Enterprises to daughter Christie in 1988, although he remained the magazine’s editor-in-chief.

In his later years, Hef was earning $4m a year – and spending about $40,000 a month on food and entertaining.

At least half his income came from Playboy, approximately $150,000 per month, plus income from rental properties and other business interests.

The famous Mansion was sold in August 2016, to Daren Metroupoulos for $100 million. Metroupoulos, the 33-year-old son of billionaire investor C. Dean Metropoulos, purchased the home under the condition that Hefner be allowed to remain in the residence for the remainder of his life.

The estate was initially listed for $200 million – having been bought by Hefner back in 1971 for about $1.1 million.

Hugh Hefner poses with a bevy of Playboy Bunnies (Rachel Murray/Getty Images for Playboy)
Hugh Hefner poses with a bevy of Playboy Bunnies (Rachel Murray/Getty Images for Playboy)

How much did the models earn?
The Playboy magazine was not just about soft porn (“I read it for the articles…”). The journalism and interview subjects were often of the highest quality.

But it did forge its reputation on paying beautiful women to get their clothes off. ‘Regular’ models are reportedly paid $25,000 – but stars have been tempted by $1m-plus offers to reveal all.

  • Heidi Montag – Accepted $1 million

  • Denise Richards – Accepted $2 million

  • Jennifer Aniston – Turned down $4 million offer

  • Drew Barrymore – Accepted $1 million

  • Ashlee Simpson – Turned down $4 million offer

  • Kim Kardashian – Accepted $110,000 offer

  • Lindsay Lohan – Turned down $750,000 then accepted $1 million

According to Glassdoor, the online jobs marketplace, the glamorous Bunnies make under $30,000 a year.

Hugh Hefner and third wife, Crystal at the Playboy Mansion in Los Angeles (AFP)
Hugh Hefner and third wife, Crystal at the Playboy Mansion in Los Angeles (AFP)

A family affair:
He leaves four children, his legendary Playboy empire and his wife Crystal Harris, Hef’s third.

Hefner was married to Millie Williams from 1949 – 1959, with whom he had two children, Christie and David.

His was married to second wife Kimberley Conrad from 1989 – 2010, and he and the former Playmate of the Year had two sons, Marston and Cooper.

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Crystal, 30, was his third wife. It’s thought that the former Playmate of the Year will inherit nothing of his multi-million dollar fortune.

She called off their wedding in 2011 with five days’ notice. She publicly embarrassed Hef during a TV interview when she told the world they’d only ever had sex once, and that it lasted just “two seconds”. But they reconciled to marry in 2012.

Where does the money go?
The four children are expected to be the main beneficiaries, together with the University of Southern California, which he has backed throughout his life, as well as a list of charities he supported during his later years.

Philanthropy was a hallmark of the Hef; in 2010, he donated $900,000 to a conservation group in order to help preserve the famous ‘Hollywood’ sign.

Children of the Night, an organisation helping children escape prostitution, awarded Hefner with its first ever Hero of the Heart award for his extensive support for the charity.

Click below to see Playboy magazine’s most iconic covers: