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Hugh Hefner, the founder of Playboy, has died aged 91.
Hefner was born on April 9, 1926 in Chicago, Illinois, and went on to become a millionaire after founding the influential men's magazine in 1953.
On Wednesday night the official Playboy Twitter account announced: 'American Icon and Playboy Founder, Hugh M. Hefner passed away today. He was 91. #RIPHef'.
Hefner's death was confirmed in a statement from Playboy Enterprises that said he 'passed away today from natural causes at his home, The Playboy Mansion, surrounded by loved ones.'
Hefner's son, Cooper Hefner, who is also the chief creative officer of Playboy Enterprises, said: 'My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom.
'He 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.'
As news of his death spread online, celebrities gathered to pay tribute.
'RIP to the legendary Hugh Hefner! I’m so honored to have been a part of the Playboy team! You will be greatly missed! Love you Hef! Xoxo,' she tweeted.
She then added: Paris & I are reminiscing about the Playboy parties at the mansion & how much we love Hef. She’s texts me the perfect Hef emojis,' followed by eight Playboy Bunny emojis and an old man emoji.
Larry King - Hefner's junior at 81 - tweeted: 'Hugh Hefner was a GIANT in publishing, journalism, free speech & civil rights. He was a true original, and he was my friend. Rest well Hef.'
Hefner was born Hugh Marston Hefner in 1926 and grew up in a strict Methodist family.
Despite his family's conservatism, his mother gave him a $1,000 loan to publish Playboy - 'Not because she believed in the venture,' he would later say, 'but because she believed in her son.'
The magazine hit with a splash, selling 50,000 copies of its first issue - which featured Marilyn Monroe on the cover - and went on to have seven million subscribers by its second year.
As its star rose, so too did Hefner - and he went on to amass a huge personal wealth that peaked at $200 million.
In 1971, Hefner spent $1.1 million (the equivalent of $6 million today) to buy up what would become known as the Playboy Mansion, a 21,987-square-foot LA building.
With a waterfall, swimming pool, secluded grotto and even a wine cellar hidden behind a Prohibition-era secret door, the mansion became the place for Hollywood celebrities to be seen at Hefner's famous Playboy parties.
He also became a vocal proponent of equal rights for gay people and black Americans; among those interviewed for Playboy was Malcolm X.
But as time wore on Playboy began to face stiffer competition, first from softcore pornography magazines such as Penthouse in 1969, then later from harder fare such as Larry Flynt's Hustler, which debuted in 1974.
As Playboy left the 1970s and the number of magazines focusing on models and their mammaries grew, its sales began to decline.
It also suffered with the rise of the internet, which made access to nude images - both glamorous and grim - easy for everyone.
In June 2009 the magazine cut its number of publications per year to just 11, while Hefner sold his English Manor house, located next to the Playboy Mansion, the same year for $18 million - $10 million under the asking price.
The Playboy Mansion had also begun to reflect Hefner's downturn in fortune.
In 2006, Hefner's ex-girlfriend, Izabella St James, then 31, released a book titled Bunny Tales: Behind Closed Doors at the Playboy Mansion, in which she lamented the state of the one-palatial home.
St James, who entered the home in 2002 as one of Hefner's seven 'girlfriends,' described 'mismatched, random pieces of furniture... as if someone had gone to a charity shop and bought the basics for each room.'
She claimed things got worse when Holly Madison became Hefner's 'Girlfriend No. 1' - meaning that she could move into his room, along with her dogs.
'They weren’t house-trained and would just do their business on the bedroom carpet,' she wrote.
'Late at night, or in the early hours of the morning - if any of us visited Hef's bedroom - we'd almost always end up standing in dog mess.
'Everything in the Mansion felt old and stale, and Archie the house dog would regularly relieve himself on the hallway curtains, adding a powerful whiff of urine to the general scent of decay.'
The mansion was sold last year for $100 million - half its asking price - to businessman Daren Metropoulos, who had previously bought Hefner's neighboring English Manor in 2009. He plans to to turn them into a single property.
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