Hugh Hefner: The Life of an American Icon in Images

Playboy magazine creator and American symbol Hugh Hefner passed away Wednesday at his Playboy mansion near Beverly Hills, California. He was 91. Stringer/Reuters

Hugh Hefner, the man who created Playboy magazine and converted it into one of the most famous brands in the entertainment industry, died Wednesday at his Playboy mansion near Beverly Hills, California. He was 91 years old.

With the inception of Playboy in the 1950s, Hefner became an iconoclast at a time when America was immersed in its puritanism and social norms, establishing an era of sexual revolution. He published the first Playboy magazine in 1953 when he was 27 years old.

To date, Playboy issold in more than 20 countries, and the company's trademarks generate more than $1 billion in sales annually, a statement by Playboy Enterprises said.

Hefner has been compared to trailblazers like Walt Disney and Citizen Kane, but he was "his own production" as The New York Times reported. He will be remembered as the man who always looked sophisticated, whether he was wearing his silk pajamas or a smoking jacket, hosting lavish parties and surrounded by famous and eccentric people, as well as his playmates.

Below are images of Hefner and his life as the man behind Playboy:

Hefner posed with 2016 Playmate of the Year Eugena Washington at Playboy's 2016 Playmate of the Year Announcement at the Playboy Mansion on May 11, 2016 in Los Angeles, California. Charley Gallay/Getty Images
Hugh Hefner attended the 2013 Playboy Playmate of the Year announcement and reception held at The Playboy Mansion on May 9, 2013 in Beverly Hills, California. Tommaso Boddi/WireImage/Getty Images
Hefner arrived with "Girls Next Door" Kendra Wilkinson, Holly Madison and Bridget Marquardt at the 36th AFI Life Achievement Award tribute to Warren Beatty held at the Kodak Theatre on June 11, 2008 in Hollywood, California. Frazer Harrison/Getty Images for AFI)
Hugh Hefner (center) displays a giant birthday cake to celebrate his 75th birthday as seven playmates look on in Cannes May 12, 2001. REUTERS/File Photo
Hefner is surrounded by Playmates, as he holds a pet rabbit given to him for his 72nd birthday, April 9, 1998, at the Playboy Mansion in Los Angeles. Hefner was a struggling young magazine copywriter in 1953 when he turned a $600 investment and a picture of Marilyn Monroe into one of the most successful publishing empires in history. Reuters
Hefner hosted an ESPY Awards pre-party at the Playboy Mansion in Beverly Hills, California in this July 12, 2005 file photo REUTERS/Robert Galbraith/File Photo
In October 9, 1998, Hefner received the Lifetime Achievement Award from the Friars Club, and proceeds from the event were donated to his daughter's foundation, The Christie Hefner City of Hope Fellowship in AIDS research. Reuters

Users on Twitter shared pictures of a young Hugh Hefner:

Young Hugh Hefner. RIP

— Internet Palace (@InternetPalace) September 28, 2017

paying my respects by announcing that i would totally have banged young hugh hefner

— Alex Bruce-Smith (@alexbrucesmith) September 28, 2017

Little fun fact, Hugh Hefner fought in World War II as a infantryman in 1944. Rip to the legend

— Brian Treiber (@Thrreeber) September 28, 2017

rest in peace hugh hefner, an icon whose legacy will live on forever

— a (@brokeangeI) September 28, 2017