Playboy Founder Hugh Hefner Through the Years

Hugh Hefner and his girlfriend at the time, Barbi Benton.
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Paris Hilton and Hugh Hefner in 2004.
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With even more bunnies.
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With the 'Girls Next Door' ladies in 2007.
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Hugh Hefner with some bunnies.
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Hefner and his son, Cooper Hefner.
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With Barbi Benton on his luxury DC-9 aircraft 'The Big Bunny' at Heathrow Airport.
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Hefner with Playboy Bunnies, Playmate of the Year 2013 Raquel Pomplun and Miss December 2009 Crystal Hefner in 2014.
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With 2016 Playmate of the Year Eugena Washington.
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Hefner in his natural habitat.
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With 2014 Playmate Of The Year, Kennedy Summers.
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Hefner with Roman Polankski in 1970.
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With Laurence Fishburne and Dennis Hopper.
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Hef with Izabella Kasprzyk and Bridget Marquardt in 2002.
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With two blondes.
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Hefner in 2006.
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At a private Playboy party in 2001.
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Reading from his notes before a screening of 'Bonnie and Clyde' in 2004.
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Appearing on 'The Late Late Show With Craig Ferguson' in 2006.
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Media mogul, founder of Playboy Enterprises, editor-in-chief of Playboy magazine, and of course notorious playboy, Hugh Hefner, died of natural causes in his home on Wednesday, September 26. His death, at age 91, was confirmed by Playboy Enterprises who stated that he was surrounded by loved ones and passed away peacefully.

Hefner founded Playboy in 1953 with just $600. At the time, he was 27 years old and a new father. By putting up his furniture as collateral for a loan and borrowing a few thousand dollars from family and friends, Hefner published the first issue of Playboy in December of 1953, which featured a nude centerfold of Marilyn Monroe. The publication later grew into a multimillion-dollar entertainment empire that included TV shows, a jazz festival and a chain of Playboy Clubs.

Hefner branded himself as a playboy, a symbol for the sexual revolution. He was notorious for having several young women, some of which he married, living with him at the infamous Playboy Mansion—which was equipped with 29 bedrooms. People considered Hefner to be vulgar and his magazines to be obscene, but as more people became shocked at his actions, the more successful his brand grew.

Today, Playboy is a billion dollar company, with its magazines available in over 20 countries. Through licensing deals, Playboy products generate more than $1 billion in global retail sales in more than 150 countries and territories.

Hefner lived a full life and has assured that his legacy will live on and be successful for years to come. Click through to see iconic pictures of the late Playboy founder throughout his life.

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