Hugh Hefner arrives with an entourage of Bunny Girls at London Heathrow Airport. June 25, 1966.People/Mirrorpix/Mirrorpix/Getty Images
5 of 26
Hugh Hefner and guest at a Playboy Party in Los Angeles, California,
1957. Earl Leaf/Michael Ochs Archives/Getty Images
6 of 26
Millionaire publisher of Playboy magazine Hugh Hefner poses with a bevy of bunny girls at one of America's chain of Playboy clubs. Helmut Kretz/Getty Images
7 of 26
Hugh Hefner with a ukulele. Michael Ochs Archives/Getty Images
8 of 26
Hugh Hefner and some ladies. 1970.Michael Ochs Archives/Getty Images
9 of 26
Hugh Hefner with Joan Bradshaw at a Playboy Party in Los Angeles, California, 1957.Earl Leaf/Michael Ochs Archives/Getty Images
10 of 26
Hugh Hefner with Joan Bradshaw and girls at a Playboy Party in Los Angeles, California, 1957. Earl Leaf/Michael Ochs Archives/Getty Images
11 of 26
Hugh Hefner smokes a pipe and holds a pamphlet while balancing a briefcase on his knee. 1960. Authenticated News/Getty Images
12 of 26
Hugh Hefner works on his magazine. 1961.Bettmann/Getty Images
13 of 26
Hugh Hefner in his office.Bettmann/Getty Images
14 of 26
Hugh Hefner in his Chicago home with two women.Bettmann/Getty Images
15 of 26
Hugh Hefner with Susanne Sydney at a Playboy Party in Los Angeles, California,
1957. Earl Leaf/Michael Ochs Archives/Getty Images
Hugh Hefner and Cynthia Maddox, the blonde cover girl on the February issue of his magazine, flying to New York to attend a party in honor of winners of the Playboy jazz poll. 1962.Bettmann/Getty Images
18 of 26
Hugh Hefner. 1963. Bettmann/Getty Images
19 of 26
Hugh Hefner poses with his friend Barbara Benton, 19 year old Californian coed turned actress.Bettmann/Getty Images
Millionaire Hugh Hefner during a visit to Britain. 1966. John Downing/Express/Getty Images
22 of 26
Host Phyllis Diller, and Hugh Hefner on The Beautiful Phyllis Diller Show. 1968.)Frank Carroll/NBC/NBCU Photo Bank/Getty Images
23 of 26
Playboy editor and tycoon Hugh Hefner is greeted by a group of bunny girls from his Playboy Clubs, upon his arrival at London Airport. Dove/Getty Images
24 of 26
Hugh Hefner and Roman Polanski at the movie premiere for the 1971 film version of Macbeth.Bettmann/Getty Images
25 of 26
Hugh Hefner at the Rugby Ball. 1972. Michael Ochs Archives/Getty Images
23 Photos Of A Young Hugh Hefner In His Playboy Heyday
View Gallery
Before Hugh Hefner was known as the octogenarian mogul of The Girls Next Door, he was the suave and sophisticated founder of Playboy magazine.
Though many can argue the moral or social impact of Playboy, whether for better or for worse, no one can deny the style and class that the early magazine possessed. Playboy was about projecting the image of the sophisticated bachelor, and much of creating that image was about presenting Hugh as the embodiment of those ideals.
Most will remember Hef as a pipe smoking, bathrobe wearing Casanova. However, it was his intelligence and ambitious personality that made him a fascinating, charismatic individual.
His rebellious drive and vision led him to create Playboy, a magazine with little precedence in its time.
Later TV shows may have cemented a very different image of Hugh Hefner in the minds of younger people, but at this time of his life, Hugh was one of the most revered celebrities and businessmen around.
Here are some photos of what a young Hugh Hefner looked like at the heyday of his Playboy empire, when he was at the top of his game.
Enjoy this gallery on a young Hugh Hefner? Next, check out these raw photos of The Beatles in their wild, early days. Then, see these stunning photos from skateboarding’s golden age.
Gabe Paoletti is a New York City-based writer and a former Editorial Intern at All That's Interesting. He holds a Bachelor's in English from Fordham University.
Based in Brooklyn, New York, John Kuroski is the editorial director of All That's Interesting. He graduated from New York University with a degree in history, earning a place in the Phi Alpha Theta honor society for history students. An editor at All That's Interesting since 2015, his areas of expertise include modern American history and the ancient Near East. In an editing career spanning 17 years, he previously served as managing editor of Elmore Magazine in New York City for seven years.
Citation copied
COPY
Cite This Article
Paoletti, Gabe. "23 Photos Of A Young Hugh Hefner In His Playboy Heyday." AllThatsInteresting.com, September 28, 2017, https://allthatsinteresting.com/young-hugh-hefner. Accessed August 22, 2025.
