21 Pictures That Show Just How Crazy Hugh Hefner's Life Really Was

"Life is too short to be living someone else's dream." —Hugh Hefner

Helmut Kretz / Getty Images

Millionaire publisher of Playboy magazine Hugh Hefner poses with Playmate Bunnies at one of his clubs in 1962.

Keystone Features / Getty Images

Exterior of Hefner's Playboy Club in midtown Manhattan, circa 1966.

Bettmann / Bettmann Archive

Hefner inspects new and improved fabric for the Playboy Bunny costumes in the main room of the Playboy Mansion in Chicago, circa 1966.

Edward Kitch / Edward Kitch / AP/REX/Shutterstock

Hugh Hefner "rescues" one of the swimmers in the indoor pool of his Chicago apartment in 1961.

Bettmann / Bettmann Archive

A crowd of partygoers inspect Hefner's stereo system at his Playboy Mansion in Chicago, circa 1966.

Pa Images / Getty Images

The "badge of the bunnies" on a Rolls-Royce picks up Hefner after arriving from the US in 1966.

Anonymous / Anonymous / AP/REX/Shutterstock

Hefner makes a telephone call aboard his private plane in 1970.

George Brich / AP

Playboy Bunnies welcome Hugh Hefner on the inaugural flight of his new DC-9 jetliner, The Big Bunny, on March 17, 1970.

Mirrorpix / Getty Images

Hefner arrives with an entourage of Bunnies at London Heathrow Airport on June 25, 1966. During this trip to Britain, he opened his 16th Playboy Club, located in Park Lane, London.

Herrmann / AP / REX / Shutterstock

During a press conference, a little "Bunny" offers sweets to Hugh Hefner and his girlfriend Barbara Benton after they arrived in West Berlin to shoot the film What Is A Nice Girl Like You Doing In This Business, in 1969.

Araldo Di Crollalanza / ARALDO DI CROLLALANZA/REX/Shutterstock

Hefner speaks to an audience during the release party for the Playboy 25th anniversary issue in 1979.

Lennox Mclendon / Lennox McLendon / AP/REX/Shutterstock

Hefner dances with playmate Sandra Theodore, alongside actress Rita Hayworth and her former choreographer Hermes Pan, during a fundraising party to save the Hollywood sign in Los Angeles in 1978.

Ron Galella / WireImage

Hefner and Playboy Bunnies celebrate as he receives a star on the Hollywood Walk of Fame in 1980 for his achievements in television.

Anonymous / AP / REX/ Shutterstock

Hefner poses with a group of current and former Playboy Bunnies at the Los Angeles Playboy Club in 1986.

Kip Rano / REX / Shutterstock

Luxury and high-end sports cars line the driveway of Hefner's Playboy Mansion during a party in 1991.

Brad Elterman / Getty Images

Hefner sits with his wife Kimberley and two children during an event at the Playboy Mansion in April 1994.


Hefner poses next to a laser-generated image of his head on a computer screen following a laser scanning session on Sept. 26, 2000, at the Playboy Mansion in Los Angeles. The resulting image was used to create an exact wax model of his head for a figure at the Hollywood Wax Museum.

Michael Bezjian / WireImage

Hefner and model Crystal Harris, later Crystal Hefner, attend a signing in Los Angeles on Dec. 10, 2009.

Jeff Kravitz / FilmMagic, Inc

Hugh Hefner shares a moment with Pamela Anderson during the launch party for Spike TV at The Playboy Mansion in 2003.

Denise Truscello / WireImage

Hefner looks at past Playboy covers during a Las Vegas party celebrating Playboy's 50th anniversary in 2009.

Michael Kovac / FilmMagic

Hefner arrives at the 2011 Playboy Jazz Festival at the Playboy Mansion on Feb. 10, 2011, in Beverly Hills.