Idiots Guide: Memorable Celebrity Playboy Magazine Covers









playboy usa coverOnce upon a time being the featured cover girl in Playboy Magazine was at the same time an honor, validation of sex appeal, beauty, and grace. Some of the celebrities on this list you may find surprising. Since it’s inception in 1953, Playboy, the brain child of the iconic ‘Playboy’ Hugh Hefner, has featured over seven-hundred ‘Playmates’. The 1970’s saw the popularity of Playboy explode. In fact the best single magazine release was the November 1972 edition, having sold a mind boggling 7,161,561 copies. In 2016 we will see the very last of the ‘nude’ centerfolds with Kristy Garett slated to be the last nude and 749th featured Playmate. So, without further adieu, enjoy the walk down memory lane, and revisit some of the best celebrity covers.

#14. Sharon Stone / July 1990

Playboy July 1990

Who can forget Sharon Stone‘s vividly memorable leg crossing scene in ‘Basic Instinct‘ (1992)?  She’s had a long and successful career, and somewhere in there she was able to squeeze in a Playboy Magazine appearance in the blazing summer of 1990.

#13. Marilyn Monroe / December 1953 

Playboy 1953

If Marilyn Monroe wasn’t the world’s first mega-sex symbol, then the ‘Some Like it Hot‘ (1959) star was certainly the biggest of her era. In many ways she symbolized the progress and optimism of post war America.   The winter of 1953 was made a bit warmer with this Playboy cover.  Marilyn was named ‘Sexiest Woman of the Century’ by People Magazine.

#12. Drew Barrymore / January 1995

Playboy Jan. 1995

Drew Barrymore‘s winter of 1995 appearance in Playboy was a surprising revelation, then and now. Especially since she was the adorable little girl in E.T. (1982). The youngest member of a Royal Hollywood family, Drew has carved out her own niche in show business appearing in dozens of films, and recently producing films.

#11. Goldie Hawn / January 1985

Playboy Jan 1985

During the late 1970’s and throughout the 1980’s Goldie Hawn was  Hollywood’s ‘It’ blonde. Having appeared in well over two dozen films in her illustrious career, and being married to fellow movie star Kurt Russell, that produced a movie star daughter (Kate Hudson) she has left a unique, and indelible mark on the business of show, and Playboy, in the winter of 1985.

#10. Pamela Anderson / October 1989

Playboy Oct 1989

Over the course of Pamela Anderson‘s career, she’s never been shy about showing off her body. The ‘Baywatch‘ star was in many ways the modern blonde bombshell of the late 1980’s and 1990’s. In the Fall of 1989 she graced the pages of Playboy for our viewing enjoyment, and yours, and your cousin Will, and Peter from Accounting, and, and, and…

#9. Brooke Shields / December 1986

Playboy Dec 1986

The success of 1980’s ‘The Blue Lagoon‘ introduced the world to the talent and beauty of Brooke Shields. In 1978 she starred in Louis Malle’s highly controversial ‘Pretty Baby’. Many people believing that the films theme was a bit too racy. Nevertheless her appearance in Playboy Magazine in December of 1986 was a bit more racy than that. No complaints this time. Brooke has had a long illustrious career, has aged gracefully, and retains her transcendent beauty even to this day.

#8. Joan Baez / July 1970

Playboy July 1970

Joan Baez has been a  folk singer, songwriter, musician, and political activist since the 1960’s. The fact that she was a young, and exceptional beauty in addition to those talents, was not lost on Playboy Magazine where she made an appearance in the Summer of 1970.

#7. Charlize Theron / May 1999

Playboy May 199

The only woman on this list who has both an Academy Award, and Golden Globe for Best Actress resting on her mantle, ‘Monster‘ (2003). I would imagine that fact qualifies as trivia worthy. Originally from South Africa Charlize Theron has had an amazing career by any estimation, starring in over two dozen films. Somehow she found the time to grace the pages of Playboy Magazine in the Spring of 1999. And we are not mad about it.

#6. Anna Nicole Smith / June 1993

Playboy June 1993

It could be easily argued that Anna Nicole Smith was the first of what are the now many celebrities, who are famous for being famous. She rode the media horse on her 15 minutes of fame aggressively, until her life was tragically cut short in February of 2007. During the height of her fame she made an appearance in Playboy Magazine in the Summer of 1993.

#5. Kim Kardashian / December 2007

Playboy Dec 2007

A perfect example of the aforementioned ‘Famous for being Famous‘ genre of celebrity, Kim Kardashian and her family has been in the public eye to the point of ad nauseam throughout the 2000’s. So it should come as no surprise that she found her way into the Playboy Magazine pantheon, appearing in the Winter of 2007, making it one of the best selling issues of all-time.  She is still in the midst of her career.

#4. Carmen Electra / April 2003

Playboy April 2003

Many of you know Tara Leigh Patrick by her stage name Carmen Electra.   Her career has included modeling, television and film acting, singing, and dancing. She worked with Pamela Anderson (also on this list) on the hit show ‘Baywatch‘, has starred in dozens of film projects, and was an original member of ‘The Pussycat Dolls‘. Simply put, Carmen is a stunning beauty with transcendent sex appeal. She dropped in to do a spread in Playboy Magazine in the Spring of 2003. To the delight of the very many.

#3. Mariah Carey / March 2007

Playboy March 2007

Long Island, New York’s own Mariah Carey is without question, the most gifted celebrity on this list. Her voice is both powerful and angelic. Music fans worldwide have shown their agreement with that statement by purchasing some 200 million of her records. In fact her debut album ‘Mariah Carey‘ (1990) went platinum many times over. It also contained four (4) number one pop singles! Not to be outdone by her lyrical talents, and success, in the Spring of 2007 she graced the cover of Playboy Magazine to show off her beautiful physical gifts. It’s almost unfair.

#2. Madonna / September 1985

Playboy Sept 1985

It could be argued that Madonna, her music, and style created trends, influenced fashion, and defined feminism in the 1980’s. He second studio album ‘Like a Virgin‘ (1984) burned like a comet through the pop music universe. The album went…wait for it…Diamond in sales, topping 25 million copies in seven (7) countries world-wide. For over a decade Madonna was feminine empowerment and sexuality incarnate. In concert with her style she too was featured in Playboy Magazine in the Fall of 1985.

#1. Cindy Crawford  / July 1988

Playboy July 1988

In the rarified air of the Super Model Cindy Crawford was perhaps the very best ever. Her beauty is breathtaking, even today. In the world of modeling, business acumen, and overall influence, Cindy is without question an all-time great. In 1995, Forbes magazine credited her as the highest paid model. Ever. She helped define what it is to be a ‘Super Model’. Not to mention you would be hard pressed to find a more stunning and elegant woman nearing 50 years of age. For many people when exceptional beauty is the question, Cindy Crawford is the answer. In the Summer of 1988 she made her contribution to the hallowed halls of Playboy Magazine cover women. In 2015-16 she is number one in our book.

**Honorable Mention**

#Special Selection. Darine Stern / October 1971

Playboy Oct. 1971

Although Darine Stern was not the first African-American woman to appear in the iconic men’s magazine, she was the very first to grace Playboy’s cover in the fall of 1971. A fantastic cover wouldn’t you say?












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