Life and Times of Hugh Hefner

Playboy publisher Hugh Hefner died Wednesday, Sept. 27, 2017, at age 91, Playboy Enterprises announced. The company said Hefner peacefully passed away on Wednesday from natural causes at his home, the Playboy Mansion, surrounded by loved ones. After hitting newsstands in 1953, Hefner's Playboy magazine quickly expanded into a multimillion-dollar enterprise. Hefner epitomized the lifestyle promoted in his magazine. Surrounded by beautiful women, Hefner made a name for himself as a charismatic icon and a spokesperson for sexual revolution.

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Amanda Martinez/AP
Playboy magazine magnate Hugh Hefner, second from left, is shown with stewardesses in bunny-style costumes as they arrive in his five-and-a-half million-dollar black jet plane in Chicago, Illinois, on Feb. 17, 1970. The private DC-9 jet includes a bedroom in the tail.
Hugh Hefner and his girlfriend Barbara Benton, 19-year-old coed turned actress, are surrounded by Bunny Girls at the Playboy Club in London on September 5, 1969.
Some of the Playboy bunnies, who staged a demonstration on June 18, 1975, in Chicago, display their signs for all to see. The bunnies are protesting the clubs rules governing their social lives, and espousing more personal freedom.
Amanda Martinez/AP
In 1980 Hugh Hefner is honored by the Hollywood Chamber of Commerce in Los Angeles with the placing of his star in the Hollywood Walk of Fame. Honorary Mayor of Hollywood, Monty Hall, right, holds the rope with Hefner.
Lennox McLendon/AP
Hugh Hefner posed with actresses Vivian Blaine (left) and Rita Hayworth in front of a replica of the Hollywood sign during a fund-raising party to save the landmark in 1978. Hefner stepped in again in 2010, donating $900,000 to stop the sign from being torn down.
Hugh Hefner and girlfriend Barbara Benton arrive in Germany in 1969. The couple lived together for eight years, during which Benton appeared on the Playboy cover four times.
Corrie Lacey/AP
Hugh Hefner opened the first Playboy Club in 1960, in Chicago, Illinois. The club introduced the first "Playboy Bunnies" -- waitresses who wore a bunny suit costume consisting of a corset, bunny ears, a collar, cuffs and a fluffy tail.
Corrie Lacey/AP
Hugh Hefner looks over proof sheets for a 1961 issue of Playboy. Since starting publication in 1953, circulation of his magazine had grown to more than one million in eight years.
Kristian Dowling/AP
Playboy, a groundbreaking publication featuring photos of nude women, quickly expanded into a multimillion-dollar enterprise after hitting newsstands in 1953. Surrounded by beautiful women, Hefner made a name for himself as a spokesperson for sexual revolution.
Elayne Lodge/AP
Donning his signature red-satin pajamas, Hefner holds the first issue of Playboy, which featured actress Marilyn Monroe.
Ron Galella/WireImage
Christie Hefner embraces her father at the "Special 25th Annual Awards Winners" party in 1979.
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Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport.
Mark Elias/AP
Hugh Hefner kissed two-year-old son Marston during a tour of the Playboy corporate headquarters in 1992. Hefner was in town for the Chicago Film Festival premiere of "Hugh Hefner: Once Upon a Time," a documentary of the publisher's life.
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Hugh Hefner, with wife Kimberly Conrad and sons Cooper and Marston, hosted a luncheon in April 1994. Hefner and Conrad married in 1989, the same year she was named Playmate of the Year.
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Hugh Hefner and younger brother Keith attended a "Get Smart" reunion at California's Museum of Television & Radio in 2003.
Damian Dovarganes/AP
Anna Nicole Smith first appeared on the cover of Playboy in March 1992. Hefner put Smith on the cover four times during her life, and devoted a tribute issue to her after her death.
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Hugh Hefner introduced the TV show "The Girls Next Door" in 2005. The show, which focused on the lives of Hefner's live-in girlfriends -- Holly Madison, Bridget Marquardt and Kendra Wilkinson -- was broadcast on E! and ran for six season.
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The Mansion has an extensive film collection, and a "Saturday Night Mansion Movie" screened every week. Hefner's favorite film, "Casablanca," was shown every year on his birthday weekend.
Kristian Dowling/AP
Hugh Hefner holds a Guinness world record for his personal scrapbook collection -- a hobby he began in 1943. His scrapbooking room, housed on the second floor of the Playboy Mansion, has more than 2500 volumes.
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Hugh Hefner and girlfriends Holly Madison, Bridget Marquardt and Kendra Wilkinson attend the 2007 Toyota Pro/Celebrity Race in Long Beach, Calif., where Hefner served as the grand marshal and Wilkinson (left) participated in the race.
Matt Sayles/AP
Hugh Hefner and girlfriend Holly Madison hosted the 2008 Playmate of the Year Luncheon at the Mansion in Los Angeles. Madison, Hefner's live-in girlfriend of seven years, and the Playboy mogul split later that year.
Chris Pizzello/AP
Hugh Hefner and girlfriends Crystal Harris and twins Kristina and Karissa Shannon became the stars of the 2009 season of "The Girl's Next Door."
Reed Saxon/AP
Hugh Hefner was seen at the 32nd Annual Playboy Jazz Festival in June 2010. The festival, founded by Hefner, was first held in Chicago. It moved to the Hollywood Bowl in Los Angeles in 1979, and has been held there every year since.
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Hefner arrived at Stansted Airport in June 2011 to launch a new Playboy Club in Mayfair. The club's opening welcomed the iconic Playboy Bunny back to London after a 30 year absence.
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The 86-year-old Playboy magazine founder married 26-year-old "Playmate of the Month" Crystal Harris at a private Mansion ceremony in 2012. Harris broke off a previous engagement to Hefner just before they were set to be married in 2011.
Matt Sayles/AP
Identical twins Karissa and Kristina Shannon, Hugh Hefner, second from right, and Crystal Harris, right, arrive at the taping of the American Film Institute Life Achievement Awards honoring actor Michael Douglas in Culver City, California, June 11, 2009.
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Hugh Hefner greets fans as they sign copies of the November issue of Playboy at Virgin Megastore Times Square Oct. 11, 2005, in New York City.
This image provided by the Playboy Jazz Festival shows, from left, Hugh Hefner, 2013 Playmate of the Year Raquel Pomplun and George Lopez, backstage at the 35th Anniversary of the Playboy Jazz Festival at the Hollywood Bowl, June 16, 2013, in Los Angeles.
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Hugh Hefner poses 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.
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Model Crystal Harris and Hugh Hefner attend the annual Halloween Party, hosted by Playboy and Hugh Hefner, at the Playboy Mansion on October 24, 2015, in Los Angeles, California.
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