1950s
Born April 9, 1926, Hefner parlayed $8,000 in borrowed money in 1953 to create Playboy, the hot-button media empire renowned for a magazine enriched with naked women and intelligent interviews just as revealing.
Born April 9, 1926, Hefner parlayed $8,000 in borrowed money in 1953 to create Playboy, the hot-button media empire renowned for a magazine enriched with naked women and intelligent interviews just as revealing.
While most famous for Playboy, the businessman dabbled in all forms of media, including hosting his own TV shows, beginning with Playboy’s Penthouse in the late 1950s and early '60s. Shot in his hometown of Chicago and syndicated, the show featured Hefner in a tuxedo and smoking a pipe surrounded by “playmates” and interviewing such celebrities as Bob Newhart, Don Adams and Sammy Davis Jr. The show boosted his personal and professional reputation and promoted what eventually became known as the “Playboy Philosophy,” a lifestyle that included politically liberal sensibilities, nonconformity and, of course, sophisticated parties with expensive accouterments and the ever-present possibility for recreational sex – though Hefner maintained he was a relative late bloomer in that department, remaining a virgin until he was 21.
Hefner followed Playboy’s Penthouse with Playboy After Dark, which had a similar format but with more rock 'n’ roll, including appearances by The Grateful Dead, Three Dog Night, Harry Nilsson and Linda Ronstadt. The syndicated Screen Gems show was taped at CBS in Los Angeles and ran for 52 episodes in 1969-70.
Hefner, seen here with a group of Playboy bunnies, also co-produced hundreds of Playboy-branded videos and a few feature films, such as Roman Polanski’s Macbeth and Monty Python’s first film, And Now for Something Completely Different, both released in 1971. He had been a sought-after guest on TV shows as far back as 1969 when he played a Control agent in an episode of Get Smart, and more recently he appeared on Curb Your Enthusiasm, Entourage and Sex and the City as well as in animated shows like The Simpsons and Family Guy.
Hefner poses with with Barbi Benton alongside his customized jet, known as "The Big Bunny."
Hefner and Benton (left) disembark "The Big Bunny" along with a group of Playboy bunnies. Hefner and Benton were a couple from 1969-27.
Barbara Patterson is crowned as "Bunny of the Year" as Hefner looks on during the Playboy Bunny of the Year Pageant, which aired on ABC.
Hefner (center) is seen with Heather Waite and Family Feud host Richard Dawson in the ABC special Playboy's Roller Disco & Pajama Party.
Hefner poses with Candy Loving (left) and Debra Jo Fondren for the Playboy's 25th Anniversary Celebration special.
Hefner poses with Kimberley Conrad (right, center) surrounded by aspiring Playmates on the lawn of the Playboy Mansion in Los Angeles. Hefner lived in the 22,000-square-foot house in Los Angeles for more than four decades and hosted famously decadent parties there that attracted celebrities A-list through D. The house sold for $100 million in August 2016 with the provision that Hefner be allowed to live there the rest of his life.
Hefner poses with daughter Christie Hefner. Along with son David (born in 1955), Christie (born in 1952) was one of two children Hefner had with Mildred ("Millie") Williams. The couple were married from 1949-59.
Hefner and Conrad pose for Playboy's 35th anniversary. Hefner and Conrad were married from 1989-99 and had two sons together: Marston Glenn (born in 1990) and Cooper Bradford (born in 1991).
Directed by Robert Heath, the 1992 documentary Hugh Hefner: Once Upon a Time, about the life and times of Hefner, showed how he changed the sexual climate of America.
In a still from Hugh Hefner: Once Upon a Time, Hefner is seen hanging out with Barbi Benton, also known for her role as a regular on Hee Haw, and other Playboy bunnies. Hefner and Benton dated from 1969-76.
In another shot from Hugh Hefner: Once Upon a Time, Hefner is seen catching up on work while lounging on his bed.
Hefner poses with several Playboy bunnies.
The captain's hat is one of Hefner's trademarks.
Wearing more of his trademarks: a silk smoking jacket and pajamas.
Hefner with daughter Christie, who served as chairman and CEO of Playboy Enterprises until 2009.
Hefner with then-girlfriends Holly Madison (seated), Kendra Wilkinson (left) and Bridget Marquardt in a publicity shot for their E! series The Girls Next Door.
Hefner walks the red carpet with (from left) Holly Madison, Bridget Marquardt and Kendra Wilkinson at the premiere of The House Bunny. Hefner had a cameo in the movie, which told the fictional story of a Playboy “bunny,” played by Anna Faris, who has been kicked out of the Playboy Mansion.
Hefner poses with son Marston Hefner and his girlfriend, October 2010 Playboy Playmate of the Month Claire Sinclair, alongside a group of Playmates for Hef's 85th birthday and son Marston Hefner's 21st birthday at the Palms Casino Resort in Las Vegas.
From left: Model Hiromi Oshima, Hefner's son Cooper, Hefner's third wife Crystal Harris, Hefner, Beverly Hills Mayor William W. Brien, Playboy CEO Scott Flanders, producer Richard Rosenzweig and model Deanna Brooks attend Playboy Enterprises' celebration of the return of Playboy headquarters to Beverly Hills.
Hefner is honored with the Distinguished Service Award in Memory of Johnny Grant at the 2012 Heroes of Hollywood Luncheon in Hollywood.
Hefner and son Cooper attend the annual Midsummer Night's Dream Party at the Playboy Mansion.
Hefner takes a photo with 2016 Playmate of the Year Eugena Washington at the 2016 Playmate of the Year announcement at the Playboy Mansion.