Silk-robed lothario, Hugh Hefner, not only changed how pornography is consumed in mainstream media, but he also made an indelible mark on popular culture. Famed for his larger-than-life personality, Hefner became shrouded in an air of the urban legend that not even a myriad of interviews and his own reality television show could shake.
Hefner launched Playboy magazine in 1953 with only $600, and it went on to play a pivotal role in the sexual revolution of the 60's. The men's magazine eventually turned into a multi-million dollar business which grew to include a chain of Playboy Clubs, featuring cocktail waitresses adorned in the brand's infamous cottontails and bunny ears.
In the early days of the publication, the magazine was one of the few places where people could find female nudity. However, Playboy looks very different today than it did back in the 1950's. The internet has made pornography available to anyone with a connection, and as such, the magazine's offerings began to look tame in comparison. In response to this shift, the publication attempted to make its product more accessible and less NSFW by ceasing to publish nude photographs in August of 2014. Its print edition followed suit until 2017 when Hefner's son, Cooper, said that "removing it entirely was a mistake".
These 27 images document just how much the American brand has evolved since its conception over 60 years ago.
1. December 1953 - Marilyn Monroe
Enduring icon, Marilyn Monroe, graced the first cover of Playboy magazine. While Monroe never actually posed for the publication, Hefner purchased a photograph of the actress from a nude calendar.
2. June 1962 - The Bikini Arrives
The image of a woman posing on a beach in a bikini marked the first time the swimsuit was featured on a Playboy cover.
3. May 1964 - Donna MichelleThis artistic shot of Playmate Donna Michelle using her legs to recreate the iconic Playboy logo was later immortalised as a postage stamp.
4. April 1969 - Lorna HopperPlaymate of the Month, Lorna Hopper's cover is one of the top-selling issues of Playboy. It was also one of the first covers to challenge gender norms, with a nude Hopper dressed in a men's tie.
5. July 1970 - Joan BaezFolksinger, Joan Baez, was one of the first celebrities to appear on the cover of the magazine.
6. October 1971 - Darine SternStern was the first black model to be featured alone on the cover of Playboy.
7. October 1977 - Barbara StreisandAfter winning an Oscar for her song "Evergreen", Streisand appeared on the cover of the publication, for the first and only time.
8. October 1978 - Dolly PartonThe beloved country singer graced the cover to promote her 20th album, Heartbreak.
9. December 1978 - Farrah FawcettThe Charlie's Angel graced the cover of Playboy shortly after leaving the hit 70's show.
10. September 1979 - Women of Ivy League Revealed
The highly contentious cover mimicked the layout of a college newspaper and featured several women from Ivy League institutions.
After she appeared as a veritable beach goddess in 10, Derek posed for Playboy. The issue was naturally a top-seller.
12. November 1980 - Women of the US GovernmentThis highly controversial cover featured a spread of government employees posing semi-nude, it resulted in two women from the US Navy being court-martialed for appearing in the publication.
13. December 1983 - Joan CollinsCollins appeared in a red number for the magazine's Christmas issue.
14. September 1985 - MadonnaPlayboy published nude photographs of Madonna that were taken in New York in 1978, back when she was a struggling artist.
15. December 1986 - Brooke ShieldsJust after her 21st birthday, Brooke Shields graced the cover of Playboy for their annual Christmas issue.
16. July 1988 - Cindy CrawfordThe rising model had a tasteful spread in the publication, shot by Herb Ritts.
17. August 1989 - Women of Wall StreetPlayboy featured nine Wall Street women for their August 1989 issue. However, after the magazine went to press, seven of the nine women who posed were no longer employed in their respective positions.
18. October 1989 - Pamela AndersonJust two months after being discovered at a BC Lions Canadian Football League game in Vancouver, Anderson appeared on the cover of Playboy, catapulting her into the limelight.
19. June 1993 - Anna Nicole SmithSmith was the 1993 Playmate of the Year, and went on to appear in editorials with Guess and Lane Bryant.
20. October 1993 - SeinfeldWhile this wasn't the sexist Playboy cover to date, Jerry Seinfeld appeared on the cover during his Seinfeld run to promote the popular sitcom.
21. August 1994 - Carol ShayaIn one of the most controversial covers of Playboy of all time, NYPD officer Carol Shaya appeared on the cover of the August 1994 issue, and had a nude editorial inside too. She was subsequently fired from the NYPD for unauthorised off-duty employment and improper use of the NYPD logo and her uniform.
22. January 1995 - Drew BarrymoreVeteran wild child, Drew Barrymore, posed nude for Playboy at the age of 19.
23. April 2003 - Carmen ElectraElectra has appeared on the cover of Playboy numerous times, with the first one being back in 1996.
24. March 2007 - Mariah CareyMariah Carey appeared in Playboy to promote her comeback album, The Emancipation of Mimi.
25. December 2007 - Kim KardashianYes, even Kim Kardashian appeared on the cover of Playboy. This cover was taken just before her hit E! television show, Keeping Up With The Kardashians, aired.
26. November 2009 - Marge SimpsonMarge Simpson had her very own semi-nude photo spread in the infamous publication.
27. February 2012 - Kate Moss
Kate Moss graced the cover of Playboy for its 60th-anniversary edition.
In other news, here are 10 facts from behind-scenes of famous sex scenes that are all sorts of crazy.