The new Amazon Original series called American Playboy: The Hugh Hefner Story launches on the streaming service on Friday (7 April) and stars Matt Whelan as the young businessman starting out the men's entertainment magazine.
The docuseries combines archival footage, interviews and cinematic re-enactments to tell the story of the Playboy magazine founder's life with accuracy.
After the first issue in 1953 featuring Marilyn Monroe was a huge success, the cover stars have gotten more high-profile and world famous over the years.
Here are a few of the most surprising celebrities to have graced the cover of the iconic men's publication:
Drew Barrymore – Issue January 1995
The ET actress was only 19 years old when she posed for Playboy in January 1995 in the midst of her wild child days. We may know her as a wholesome Hollywood movie star now, but Barrymore was going to Studio 54 and doing drugs at this time of her life.
Cindy Crawford – Issues July 1988 (pictured), May 1996 and 1998
One of the most successful supermodels of all time and at one point the highest paid, Crawford quite liked taking her clothes off for Hefner's magazine as she was the cover star not once, not twice, but three times in total. The 5 foot 9 model was known for her innocent persona, making her an unlikely Playboy pin-up.
Kim Kardashian – Issue December 2007
With her sex tape fame, hourglass curves and smouldering looks, global superstar Kardashian is undoubtedly the perfect Playboy cover girl and gladly posed for the 2007 Christmas issue. Dubbed 'Hollywood's new sex star' by the publication, Kardashian is still proud of her appearance in the magazine from a decade ago and has posted flashback photos of the shoot on her app.
Jessica Alba – Issue March 2006
Another surprising cover girl may be the Into the Blue actress, who also prides herself on her clean-cut image. But all is not as seems upon first glance. Alba became a Playboy model without her permission when a bikini-clad image of her appeared on the March 2006 without her knowledge or approval. Hefner personally apologised for the incident and offered to donate money to her favourite charities, with Alba claiming she had forgiven the publication.
Anna Faris – Issue September 2008
Scary Movie star Anna Faris is better known for her hilarious wit than lack of clothing, but the blonde-haired actress nailed her Playboy cover back in 2008 while promoting her movie House Bunny. She played a sexy Playboy Bunny in the film who is thrown out of the famous mansion by a jealous rival, though the cover still caught everyone by surprise.
Joan Collins – Issue December 1983
She has has oozed sex appeal ever since she has been around, but the shocking thing about Collins' Playboy cover is that she was 50 years old at the time. The old Hollywood actress, now 82 and still thriving, banned the stigma surrounding sexiness and mature women, wowing in her red plunging gown for the cover.