Hugh Hefner's most iconic Playboy front covers

The man who created Playboy magazine, Hugh Hefner, has died aged 91.

He began the influential, adult magazine in 1953.

He also created the Playboy mansion, complete with hundreds of supermodels dubbed the Playboy bunnies.

His son Cooper said his father was a "leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom."

It all began for Hugh Hefner more than 60 years ago in his kitchen.

Tweet from Playboy says American Icon and Playboy Founder, Hugh M. Hefner passed away today. He was 91. #RIPHef

He published the first Playboy with the star of the moment, Marilyn Monroe, on the cover.

Since then, the front covers have ranged from raunchy to chic.

In 1971, Darine Stern became the first African American woman to appear on the front cover of the magazine.

Madonna appearing on the September 1985 cover

Former Baywatch actress Pamela Anderson has appeared on the cover more times than any other model.

Future US president President Trump appeared in the magazine.

The future president of the United State appeared on the front cover of the magazine.

He was the fourth man to feature on the front cover.

In a recent interview, Cooper Hefner, son of Hugh Hefner and chief creative officer of the magazine said they were embarrassed he was once on the magazine.

Anna Nicole Smith first gained popularity by appearing on the magazine.

At the age of 26, she went on to marry 89-year-old oil tycoon J Howard Marshall a year after this shoot.

Paris Hilton tweeted her front cover saying: Love you Hef 💋 #Legend #RIPHEF

Kate Moss appeared on the 60th anniversary issue of the magazine.

Last year Playboy announced the magazine wouldn't be featuring nude models in its magazine.

It reversed that decision in February, saying it "was a mistake".

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