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Dec. 1953: Marilyn Monroe
The Most Iconic Playboy Covers
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Dec. 1986: Brooke Shields Timed to the actress's 21st birthday, Shields graced the cover of Playboy for their annual Christmas issue.
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."
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Jan. 2000: Collector's Edition In honor of the millenium, Playboy released this collector's edition featuring some fantastic cover art.
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.
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.
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.
Nov. 2009: Marge Simpson One of the more unorthodox Playboy covers featured The Simpsons matriarch Marge with an accompanying semi-nude photo spread.
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.
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.
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.”
Kate Moss The supermodel apparently lost her contact lens when posing for Playboy's 60th anniversary January/February 2014 issue.
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