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Hugh Hefner (1926-2017): Life and times of a publishing legend in pictures

Playboy magazine founder Hugh Hefner poses for a portrait at his Playboy mansion in Los Angeles, California, July 27, 2010.
Lucy Nicholson | Reuters

Hugh Hefner, who died this week at age 91, was the iconic and entrepreneurial mastermind behind the Playboy brand and enterprise.

After founding Playboy magazine in 1953, "Hef" built a publishing empire that spanned more than 60 years by featuring photos of nude women, in-depth interviews and the writings of literary luminaries, all instrumental in promoting the sexual revolution.

Beyond the magazine, Hefner had an eclectic career that included a chain of Playboy nightclubs across the United States and abroad, a television show called "Playboy After Dark" and countless cameos in feature films and television.

The following are some of the photos that captured the life and times of the quintessential bachelor who lived in the ultimate bachelor pad known as the Playboy Mansion.

An eye for beauty

Hugh Hefner who launched one of the most controversial magazines in publishing history, views photographs in his Chicago office.
Bettman Collection | Getty Images

The publisher of one of the most controversial magazines in history views photographs in his Chicago office.

Marilyn Monroe helps launch an empire

Hugh Hefner holds a copy of the first Playboy Magazine cover that featured Marilyn Monroe.
AP

Playboy's first issue, in 1953, featured Marilyn Monroe on the cover. She was the only model named "Sweetheart of the Month." Hefner later changed this designation to "Playmate of the Month."

The Ultimate Bachelor

(l-r) Playboy Playmates Claudia Jennings, Monique St. Pierre, Playboy founder Hugh Hefner, Playmates Dorothy Stratten, Connie Kreski, Angela Dorian celebrating Playboy Magazine's 25th Anniversary All-Day Saturday Playmate Reunion at the Playboy Mansion West on September 8, 1979 in Los Angeles, CA.
NBC Photo Bank

At the 25th anniversary celebration, Hefner is joined by some of his "Playmates" at the Playboy Mansion West.

The Playboy jet 'Big Bunny'

Photo taken on August 30, 1970 shows US Playboy Magazine publisher Hugh Hefner (top), his girlfriend actress Barbara Benton and other playmates arriving at Le Bourget airport with the Playboy jet 'Big Bunny'.
STR | AFP | Getty Images

In this photo taken on Aug. 30, 1970, Hefner puts his arm around girlfriend Barbi Benton after arriving at Paris' Le Bourget Airport with the Playboy jet "Big Bunny."

The Playboy Clubs

Exterior of Hugh Hefner's 'Playboy Club' in midtown Manhattan, New York.
Keystone Features | Getty Images

Hefner opened up a chain Playboy nightclubs and resorts that featured Playboy Bunny cocktail waitresses. The first one was opened in Chicago in 1960, followed by clubs in New York, pictured above in 1962, Boston, Miami, Los Angeles and Dallas and in London, Cancun, Jamaica and Japan.

The Playboy Bunny Costume

A group of Playboy Bunnies line up for inspection by Hugh Hefner, publisher of Playboy magazine, in the main room of Playboy Mansion in Chicago. Hefner is inspecting the new improved fabric for the costumes.
Bettman Collection | Getty Images

Playboy Bunnies line up in the Playboy Mansion in Chicago. Hefner is inspecting new fabric for the costumes.

Hef as movie producer

Roman Polanski and Hugh Hefner at the movie premiere for the 1971 film version of Macbeth.
Getty Images

Director Roman Polanski with Hefner and Benton at the premiere of the 1971 film version of "Macbeth." Hefner invested $1.5 million in the production.

Playboy at the NYSE

Playboy Chairman Emeritus and Founder Hugh Hefner (C) is surrounded by his girlfriends Sandy and Mandy Bentley and New York Stock Exchange Chairman Richard Grasso (L) and NYSE President William Johnston (R) before Hefner rang the closing bell at the end of the trading day 13 April, 2000.
Ray Abrams | AFP | Getty Images

Hefner (C) is surrounded by girlfriends Sandy and Mandy Bentley and New York Stock Exchange Chairman Richard Grasso (L) and NYSE President William Johnston (R) to ring the closing bell on April, 13, 2000.

Hef in London

Playboy founder Hugh Hefner (centre) arrives at Stansted Airport on June 2, 2011 in Stansted, England. The photograph is a recreation of a picture originally taken in the 1960's, with ten of the new London Bunnies. Mr Hefner is back in the UK to mark the launch of the new Playboy Club in Mayfair, which opens on June 4. The club's opening will welcome back the iconic Playboy Bunny to London after a 30 year absence.
Getty Images

Hefner arrives at Stansted Airport on June 2, 2011. The photograph is a re-creation of a picture originally taken in the 1960s, with 10 new London Bunnies. Hefner was back in the U.K. to mark the launch of the new Playboy Club.

Reality TV Stars

Kendra Wilkinson, Bridget Marquardt, Hugh Hefner and Holly Madison.
Laurence Cottrell | FilmMagic | Getty Images

Hefner poses with Kendra Wilkinson, Bridget Marquardt and Holly Madison. The three former Playboy models starred with him on the E! reality television show "The Girls Next Door," which ran from 2005-2010.

Hef remarries

In this April 26, 2010 file photo, Hugh Hefner, left, and Crystal Harris arrives at the premiere of "Iron Man 2" at the El Capitan Theatre in Los Angeles. The 86-year-old Playboy magazine founder exchanged vows with his "runaway bride," Crystal Harris, at a private Playboy Mansion ceremony on New Year's Eve. Harris, a 26-year-old "Playmate of the Month" in 2009, broke off a previous engagement to Hefner just before they were to be married in 2011.
Matt Sayles | AP

At age 85, Hefner married Crystal Harris, 60 years his junior, during a private ceremony at the Playboy Mansion in Holmby Hills, California, on New Year's Eve 2012.

Family Business

Hugh Hefner dances with his daughter Christie, the magazine's CEO, at her wedding to lawyer Bill Marovitz at the Four Seasons Hotel in 1995.
Steve Liss |The LIFE Images Collection | Getty Images

Hefner dances with his daughter Christie at her wedding to lawyer Bill Marovitz in 1995. Christie, became president of Playboy Enterprises in 1982 and stepped down as CEO in 2009.

Like father like son

(L-R) Cooper Hefner, Hugh Hefner and Crystal Hefner attend Playboy Mansion's Annual Halloween Bash at The Playboy Mansion on October 25, 2014 in Los Angeles, California.
Getty Images

Cooper Hefner with his father and Crystal Hefner at the Playboy Mansion's annual Halloween Bash, Oct. 25, 2014. Cooper Hefner is chief creative officer of Playboy Enterprises.

The Playboy Mansion

View of the Playboy Mansion, owned by US Playboy Magazine publisher Hugh Hefner in Beverly Hills, California.
Gabriel Bouys | AFP | Getty Images

Dubbed the ultimate bachelor pad, the home and headquarters of Hefner's publishing empire featured 22 rooms, wine cellar, screening room, outdoor pool with its signature "Grotto," plus a zoo and aviary and tennis courts. Hefner bought the Holmby Hills mansion in 1971 for $1.1 million. It was put up for sale in 2011 for $200 million and sold for half that amount in 2016 to the next-door neighbor with the stipulation that Hefner be allowed to remain there until his death. He died there Wednesday.

Hef and Marilyn forever

Hugh Hefner will be buried beside Marilyn Monroe at Westwood Village Memorial Park and Mortuary in Westwood, California.
Getty Images

Hefner will be interred in a mausoleum drawer next to Monroe at Westwood Village Memorial Park and Mortuary in Westwood, California.

Hugh Hefner: 1926-2017

Hugh Hefner poses at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California.
Getty Images