The document summarizes iconic covers of Playboy magazine from its first issue in 1953 featuring Marilyn Monroe to covers in the 2000s. Some of the key covers discussed include Marilyn Monroe in 1953, which sold out in weeks and launched the magazine's success, covers in the 1960s-70s featuring celebrities like Joan Baez, Dolly Parton, and Farrah Fawcett, controversial covers in the late 1970s-80s showing women from Ivy League schools and the government, and covers in the 1990s-2000s with celebrities like Carmen Electra, Charlize Theron, and Mariah Carey. Many of the covers helped promote films or albums for the featured celebrities.

1. Dec. 1953: Marilyn Monroe

2. The Most Iconic Playboy Covers

3. The most iconic Playboy magazine covers
In Dec. 1953, the first issue of Playboy magazine was released. Founded by
Hugh Hefner, the publication featured screen star Marilyn Monroe on the
cover, cost 50¢, and received a great deal of notoriety for a nude pictorial
of Monroe inside. The issue sold out in weeks, and the periodical grew to
become an iconic American men's magazine featuring a combination of
photographs of nude women, journalism, and fiction. At one point, one
quarter of all American college men were purchasing the magazine every
month.

4. Dec. 1953: Marilyn Monroe
Marilyn Monroe graced the very first
cover of Playboy magazine, which was
produced in Hefner's kitchen in Hyde
Park, Illinois. Monroe never actually
posed for Playboy. Instead, Hefner
used nude photographs taken for a
calendar.

5. June 1962: A Toast to Bikinis
This tasteful shot of a woman posing on a
beach in a bikini marked the first time a bikini
swimsuit was featured on the cover of Playboy.

6. May 1964: Donna Michelle
This cover featured Playmate Donna
Michelle using her legs to recreate
Playboy's iconic rabbit logo. It was
later memorialized as a postage
stamp.

7. 1965 This issue forgoes the standard
woman-smiling-coyly approach and
opts instead for the more mysterious
dog’s-eye-view. Apparently (at least
in the beginning) it was Hefner’s goal
to feature the bunny logo somewhere
on each cover, sometimes hidden in
the background. This time? Not so
hard to spot.

8. April 1969: Lorna Hopper
One of the top-selling issues of Playboy
was this one featuring Playmate of the
Month Lorna Hopper on the cover. It's a
mildly subversive photo challenging
traditional gender roles, featuring a
nude Hopper in a men's tie. It was
photographed by William Figge and Ed
DeLong.

9. July 1970: Joan Baez
While Playboy usually featured the
Playmate of the Month on the cover,
there were some notable exceptions.
This issue featured an eye-catching
photograph of folk singer Joan Baez
on the cover teasing an excellent
interview with the artist inside the
mag by Nat Hentoff.

10. Darine Stern, 1971
African-American model Darine Stern
changed history when she posed nude
on the cover of Playboy's October 1971
issue. While the magazine had featured
two black Playmates by this time --
Jennifer Jackson and Jean Bell -- Stern
was the first African-American model to
grace the cover.

11. Oct. 1978: Dolly Parton
The buxon blond country music
singer-bombshell graced her only
Playboy cover to promote her 20th
album, 'Heartbreaker.' Parton dressed
as a Playboy bunny for the photo.

12. Oct. 1977: Barbra Streisand
Shortly after her song "Evergreen" won her
an Oscar, Streisand appeared on the cover
of Playboy. It was her first (and only) time
gracing the cover of Playboy, and teased an
in-depth interview with the actress-singer.

13. Dec. 1978: Farrah Fawcett
One of the hottest stars of the '70s,
Fawcett graced the cover of
Playboy in Dec. 1978, shortly after
exiting the TV series Charlie's
Angels. She'd later appear in the
magazine in Dec. 1995, at the age
of 50.

14. Sept. 1979: Women of Ivy League
Revealed
This controversial cover
mimicked a college newspaper
and featured several young
women from Ivy League schools
posing. It caused a huge stir, with
several college's women's
organizations writing to complain
about how the magazine
objectified women.

15. March 1980: Bo Derek
Less than a year after appearing as a
beach beauty in braids in the movie
10, Derek was featured on the cover
of Playboy at the height of her
celebrity. The issue was, naturally, a
top seller.

16. Nov. 1980: Women of the U.S. Government
One of Playboy's most controversial
covers, this issue--featuring a 10-page
feature spread of govt. employees posing
semi-nude--was released just a few days
before Ronald Reagan was elected
president. It was condemned by
Washington Post columnist Art Buchwald,
who said "people might get the impression
that all Washington women look like these
women," and two women in the U.S. Navy
were court-martialed for appearing semi-nude
in the spread.

17. Feb. 1983: Kim Basinger
Before she was an Oscar winning
actress, Basinger posed for the cover
of Playboy shortly after starring as
Bond girl Domino Petachi in Never
Say Never Again.

18. Dec. 1983: Joan Collins
Arguably the most famous soap star
of all-time, Dynasty's Collins
appeared on the Dec. 1983 cover of
Playboy in a glittery red number for
the magazine's Christmas issue.

19. Nov. 1984: Christie Brinkley
One year after starring as the object of
Chevy Chase's desire in 1983's National
Lampoon's Vacation,
model/actress/entrepreneur Brinkley
featured on the cover of Playboy.

20. Dec. 1984: Suzanne Somers
Somers had previously appeared nude
in the 1980 issue of Playboy but the
pictures were taken back in 1970 when
Somers was a struggling model. But,
after being fired from Three's Company
in 1982, Somers appeared nude in the
1984 issue of Playboy in a bid to regain
her popularity.

21. Jan. 1985: Goldie Hawn
To promote her Dec. 1984 film
Protocol, a D.C.-set comedy which
Hawn starred in and executive
produced, the actress appeared on
the cover of Playboy.

22. Sept. 1985: Madonna
Pegged to her star turn in the film
Desperately Seeking Susan, Playboy
ran nude photos of Madonna that
were taken in New York City in 1978,
back when she was a struggling
singer.

23. Dec. 1986: Brooke Shields
Timed to the actress's 21st birthday,
Shields graced the cover of Playboy
for their annual Christmas issue.

24. Sally Field, 1986
While Sally Field did don the classic
bunny attire on the cover of Playboy
in 1986, the actress didn't appear
nude inside the magazine and
instead "gave an interview from the
heart."

25. July 1988: Cindy Crawford
One year after appearing during the
opening credits of the Michael J. Fox
film The Secret of My Success,
Crawford--then a rising model--appeared
nude in Playboy in a tasteful pictorial
shot by acclaimed photographer Herb
Ritts.

26. Aug. 1989: Women of Wall Street
Two years after Oliver Stone's Wall Street
was released, Playboy featured nine Wall
Street women in their Aug. 1989 issue.
Shortly after the issue hit stands, seven
of the nine women were no longer
employed by their respective companies.

27. Oct. 1989: Pamela Anderson
In the summer of '89, Anderson was
discovered at a BC Lions Canadian Football
League game in Vancouver after video of her
in a tight-fitting Labatt's Beer t-shirt appeared
on the stadium jumbotron. Just two months
later, Anderson was gracing the cover
of Playboy, which helped launch her modeling
and acting career.

28. 1989 Latoya Jackson posed
topless in her pictorial, and said
it was “to show my parents they
couldn’t dictate me anymore—
that I control my life.” At the
time of its release, the issue
sold over 8 million copies,
making it the highest-selling
issue of the magazine ever.

29. July 1990: Sharon Stone
To promote her starring role in the 1990
film Total Recall, Stone appeared nude in
Playboy showing off the muscle she put
on to prepare for the movie.

30. 1990 Back when Donald Trump’s comb-over
was one layer thicker, he let loose on
Playboy’s cover. Just kidding, he doesn’t do
that. The design team threw Playmate Brandi
Brandt in there to liven things up a little, but
really, it’s like using glitter to make roadkill
look alive. Maybe I’m being too harsh: from
the looks of it, Trump may have had a
stomach ache that day.

31. June 1993: Anna Nicole Smith
Smith was named the 1993 Playmate of the
Year, appearing in a stunning black-and-white
cover photo. The position led to modeling gigs
with Guess? jeans and Lane Bryant, as well as
an acting role in Naked Gun 33 1/3: The Final
Insult.

32. Oct. 1993: Jerry Seinfeld
Not exactly the sexiest Playboy
cover ever, but strange
nonetheless. Comedian Jerry
Seinfeld appeared on the cover
during his Seinfeld run to tease a
candid interview with him inside the
mag.

33. Aug. 1994: Carol Shaya
One of the most controversial
Playboy covers of all-time, NYPD
officer Carol Shaya appeared on
the cover of the Aug. 1994 issue
of Playboy with an accompanying
nude pictorial inside. She was
subsequently terminated from the
NYPD for unauthorized off-duty
employment and improper use of
her uniform and the NYPD logo.

34. Elle Macpherson, 1994
Posing in just a pair of stockings, Elle
Macpherson channeled her inner Brigitte
Bardot with her pose on the cover of
Playboy on the March 1994 issue.

35. Jan. 1995: Drew Barrymore
Before she was one of America's
Sweethearts, Drew Barrymore was a bit of a
wild child and, at the age of 19, posed nude
for Playboy. The following year, her
godfather Steven Spielberg sent her a quilt
for her 20th birthday with a note that read
"cover yourself up," as well as photos from
the Playboy spread that were mocked up so
that she appeared fully clothed.

36. May 1999: Charlize Theron
In the wake of her starring role in
The Cider House Rules, Playboy
featured up-and-coming actress
Charlize Theron on the cover,
along with nude pictures inside the
magazine. The pictures were taken
years earlier, and Theron
unsuccessfully sued the magazine.

37. Dec. 1999: Naomi Campbell
One month after appearing in the Millenium
Issue of Vogue, shot by Annie Liebovitz,
supermodel Naomi Campbell appeared on
the cover of Playboy wearing fur.

38. Jan. 2000: Collector's Edition
In honor of the millenium, Playboy
released this collector's edition
featuring some fantastic cover art.

39. April 2003: Carmen Electra
Model and actress Carmen Electra is one
of the most prominently featured women
in Playboy cover history. The first one
was back in 1996, but the best cover was
this rocker one in 2003.

40. March 2007: Mariah Carey
Yes, even the great Mariah Carey has graced
the cover of Playboy. Mimi did it to promote
her worldwide tour in the wake of her 2005
comeback album The Emancipation of Mimi.

41. Dec. 2007: Kim Kardashian
To promote the first season of the E!
reality series Keeping Up with the
Kardashians, the de facto star of the
show appeared nude in Playboy.

42. Nov. 2009: Marge Simpson
One of the more unorthodox
Playboy covers featured The
Simpsons matriarch Marge with an
accompanying semi-nude photo
spread.

43. Dec. 2009: Chelsea Handler
To promote her late night talk show on E!,
Chelsea Handler appeared on the cover of
Playboy with an accompanying semi-nude
spread inside.

44. Lindsay Lohan, 2012
Lindsay Lohan left little to the
imagination when she posed nude
while straddling a Playboy bunny seat
on the cover of the January/February
2012 issue.

45. Kate Moss
Supermodel Kate Moss, 39, graced the
cover of Playboy for their 60th anniversary
issue. Playboy's editorial director said she
was the perfect choice for the occasion.
“Having Kate Moss, a global icon and the
most important supermodel of the past 25
years, appear on our cover makes this issue
the perfect way to launch Playboy’s next 60
years.”

46. Kate Mo ss
The supermodel apparently lost her contact lens when posing for Playboy's 60th anniversary January/February 2014 issue.

47. end

48. cast The Most Iconic Playboy Covers
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