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.
The publisher of one of the most controversial magazines in history views photographs in his Chicago office.
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."
At the 25th anniversary celebration, Hefner is joined by some of his "Playmates" at the Playboy Mansion West.
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."
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.
Playboy Bunnies line up in the Playboy Mansion in Chicago. Hefner is inspecting new fabric for the costumes.
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
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.
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.
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.
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.
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.
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.
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.
Hefner will be interred in a mausoleum drawer next to Monroe at Westwood Village Memorial Park and Mortuary in Westwood, California.