60 Years of Playboy: The Most Iconic Playboy Covers, From Marilyn Monroe to Kim Kardashian

In Dec. 1953, the first issue of Playboy magazine was released. To celebrate 60 years of Playboy, The Daily Beast gives you the 35 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. To celebrate 60 years of Playboy, The Daily Beast gives you the 35 most iconic Playboy magazine covers.

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.

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.

Oct. 1971: Darine Stern

Stern was the first black woman to appear solo on the cover of Playboy. African-American model Jean Bell was featured on the Jan. 1970 cover, albeit with four other models. Stern went on to become a highly successful Ford model.

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.

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.

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.

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.

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.

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.

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.