Hugh Hefner's Most Iconic Playboy Covers
December 1953: A Major Launch
Hugh Hefner's first foray into managing his own magazine was a memorable one: The publisher was able to scrape together $8,000 to introduce the world to Playboy with the decade's hottest star, Marilyn Monroe, on the cover.
July 1955: Janet Pilgrim
While Playboy was in its second year of production, Charlaine Edith Karalus was working in the subscription department for the magazine. She agreed to pose for Playboy in exchange for an address labeler for the office. Hefner reportedly chose her stage name “Janet Pilgrim" to make fun of sexual purity.
May 1964: Donna Michelle
Playmate of the Year Donna Michelle became the brand in this issue contorting her body into the iconic bunny logo while wearing a white leotard.
June 1965: Hedy Scott
Hedy Scott became June's Playmate of the Month, exhibiting classic '60s style with chic round sunglasses, a pink head scarf and a wily smirk.
July 1969: Barbi Benton
Barbi Benton, Hefner’s girlfriend at the time, posed semi-nude, covered in a towel with a white bra next to her. She would appear on the cover three more times in the next two decades.
October 1971: Darine Stern
Darine Stern was welcomed to Playboy as the first African-American model to grace the cover. While the magazine began as a publication that shifted society’s standards of mainstream beauty, it continued shaping the nation’s culture. This cover was chosen by the American Society of Magazine Editors as one of the 40 most important magazine covers of the last 40 years in 2005.
October 1989: Pamela Anderson
Pamela Anderson made her Playboy debut in October 1989, and now holds the record for most covers (she’s posed 13 times).
June 1993: Anna Nicole Smith
Anna Nicole Smith debuted in Playboy in March 1992. It didn’t take long for her to be named Miss May 1992 and a Guess jeans spokesmodel. She became Playboy’s 1993 Playmate of the Year and appeared on three more covers.
January 2005: Jenny McCarthy
Jenny McCarthy launched her modeling career on Playboy, becoming Playmate of the Year in 1994. She returned for the January 2005 cover wearing the famous bunny suit after she expanded her career into TV and film.
January 2007: Pamela Anderson
Anderson returned to Playboy and turned heads with this no-holds-barred cover depicting the entirety of her nude torso as well as a necklace with the word "SEX" across it.
April 2009: Seth Rogen
Seth Rogen became the ninth man to grace a Playboy cover. The comedian joined the likes of Peter Sellers (1964), Burt Reynolds (1979), Steve Martin (1980), Donald Trump (1990), Jerry Seinfeld (1993) and Bruno Mars (2012), to name a few.
November 2013: A Return to Art
Playboy returned to art-inspired covers for this 2013 issue, a look it was known for in the 1950s, ‘60s and ‘70s.
January/February 2014: Kate Moss
Playboy celebrated its 60th anniversary with a Kate Moss spread, featuring an unprecedented 18 pages of photographs.