Hugh Hefner: Photos of the Playboy Founder When He Was Young

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January 25, 2022 1:25PM EST
Hugh and Crystal Hefner
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Hugh Hefner was the iconic founder of the Playboy brand. Look back at photos of the legend here.

The late Hugh Hefner was famous for founding the groundbreaking Playboy Enterprises. After first publishing the men’s entertainment magazine in 1953 with a cover of Marilyn Monroe, he would go on to open clubs, casinos, and hotels with the iconic Playboy name and logo. He even had a few television stints with the brand. In more recent years, he starred in the reality TV series ‘The Girls Next Door.’

Born on April 9, 1926, in Chicago, Illinois, Hugh was the eldest of two sons born to Grace and Glenn Hefner, who were strict Methodists. After a stint at Northwestern University, Hugh would go on to borrow money from his mother to start up his own publication. Originally titled ‘Stag Party,’ Hugh changed the name to Playboy and the rest is history.

Hugh was just as famous for his love life as he was for his business accomplishments. From dating models to actresses to his very own Playboy centerfolds, Hugh was soon recognized for having multiple live-in girlfriends at the Playboy Mansion. However, he only married three women: Mildred Williams, Kimberley Conrad, and Crystal Harris. He has four children between his three wives. Sadly, Hugh passed away in 2017 at the age of 91.

Keep scrolling to see the best photos from Hugh’s legendry life.

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Hugh Hefner Poses In His Office

Hugh Hefner Poses In His Office
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Hugh Hefner is seen here in his office circa 1950s. As the editor of Playboy Magazine, he chose the centerfolds for the adult magazine.

February 28, 2020, 9:19AM
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Hugh Hefner Relaxes On The Playboy Airplane

Hugh Hefner Relaxes On The Playboy Airplane
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Hugh Hefner is seen on the Playboy airplane in 1970. The posh plane was known as ‘The Bug Bunny.’

February 28, 2020, 9:19AM
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Hugh Hefner Takes A Call In His Private Plane

Hugh Hefner Takes A Call In His Private Plane
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Playboy magazine publisher Hugh Hefner is shown aboard his private plane in 1970. He appeared to enjoy sitting cross-legged in the comfy cabin.

February 28, 2020, 9:19AM
4 of 18

Hugh Hefner Poses Outside Of Playboy Mansion

Hugh Hefner Poses Outside Of Playboy Mansion
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Hugh Hefner is spotted outside his Playboy mansion in Los Angeles in 1975. The home became known for its wild parties. 

February 28, 2020, 9:19AM
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Hugh Hefner Swims With Playboy Bunnies

Hugh Hefner Swims With Playboy Bunnies
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Hugh Hefner at his mansion in 1975. The mogul enjoyed a day swimming in the famous grotto with some of his models.

February 28, 2020, 9:19AM
6 of 18

Hugh Hefner Plays Pinball At His Mansion

Hugh Hefner Plays Pinball At His Mansion
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Hugh Hefner plays pinball with models at his mansion in 1975. Hugh was enjoying his iconic smoking pipe while he played the game. 

February 28, 2020, 9:19AM
7 of 18

Hugh Hefner Reads The Paper At His Mansion

Hugh Hefner Reads The Paper At His Mansion
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Hugh Hefner is spotted reading the newspaper in his mansion in 1975. A young woman joins him for the breakfast ritual.

February 28, 2020, 9:19AM
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Christie Hefner, Hugh Hefner & Grace Hefner Pose Together At A Gala

Christie Hefner, Hugh Hefner & Grace Hefner Pose Together At A Gala
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Christie Hefner, Hugh Hefner and Grace Hefner are pictured together in 1980. The three generations of Hefners look adorable together.

February 28, 2020, 9:19AM
9 of 18

Hugh Hefner & Family Enjoy Playboy’s 40th Gala

Hugh Hefner & Family Enjoy Playboy’s 40th Gala
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Hugh Hefner, wife Kimberley Conrad and their two sons enjoy a party in 1994. They were celebrating Playboy’s 40th anniversary.

February 28, 2020, 9:19AM
10 of 18

Hugh Hefner & Family Attend Star Wars Screening

Hugh Hefner & Family Attend Star Wars Screening
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Hugh Hefner, wife Kimberly and their kids attend a screening of ‘Star Wars’ in 1997. The entire family was dressed up for the red carpet affair.

February 28, 2020, 9:19AM
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Hugh Hefner Poses With Playmates In London

Hugh Hefner Poses With Playmates In London
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Hugh Hefner poses with Playboy Playmates in London. The mogul was surrounded by a bevy of beautiful models.

February 28, 2020, 9:19AM
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Hugh Hefner Attends AFI Awards

Hugh Hefner Attends AFI Awards
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Hugh Hefner attends the AFI Awards in Beverly Hills in 1991. He looked quite dapper in his classic tuxedo.

February 28, 2020, 9:19AM
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X-Games Gala At Playboy Mansion

X-Games Gala At Playboy Mansion
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‘A Day At the Mansion’ gala celebrates the X-Games in 2003. Athletes enjoyed the swimming pool and vast grounds for a relaxing day off from competition.

February 28, 2020, 9:19AM
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Hugh Hefner Attends Playboy’s 50th Anniversary

Hugh Hefner Attends Playboy’s 50th Anniversary
Jason Szenes/EPA/Shutterstock

Playboy founder and publisher Hugh Hefner arrives at the Playboy 50th Anniversary party. He kept it casual with a red shirt and dark jacket. 

February 28, 2020, 9:19AM
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Hugh Hefner Attends Book Signing

Hugh Hefner Attends Book Signing
Angello P/Shutterstock

Hugh Hefner attends a book signing for his ‘Playboy 50 Years: The Cartoons’ publication in 2004. The icon was all smiles and ready to give his signature. 

February 28, 2020, 9:19AM
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Hugh Hefner Attends Hollywood Luncheon

Hugh Hefner Attends Hollywood Luncheon
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Hugh Hefner attends ‘Heroes of Hollywood’ Awards Luncheon at the Taglyan Culural Complex’ Los Angeles in 2012. He held up a photo of his own Walk of Fame star.

February 28, 2020, 9:18AM
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Hugh Hefner Attends The Playmate Of The Year Party

Hugh Hefner Attends The Playmate Of The Year Party
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Crystal Hefner, Hugh Hefner and Cooper Hefner attend the Playmate of the Year Luncheon honoring Raquel Pomplun in 2013. The family looked happy to be at the Los Angeles fete.

February 28, 2020, 9:18AM
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Hugh Hefner Death Certificate

Hugh Hefner Death Certificate

Hugh Hefner’s death certificate is revealed. The icon died in September of 2017. 

October 3, 2017, 2:53PM