For many icons, from Madonna to Naomi Campbell, a Playboy cover is a rite of passage. The photos are visceral, tantalizing, and for many celebrities, incredibly empowering. Marilyn Monroe kicked off the trend in 1953 as the first-ever Playboy cover star, and dozens of icons since have adorned the cover of the magazine, now a byword for unapologetic sexiness. If you forgot about the icon covers from Kim Kardashian, Anna Faris, Brooke Shields, and more, well—we're here to remind you. Let's take a trip down memory lane, shall we?
Issue: December 1953
Marilyn Monroe became the first-ever Playboy cover girl for the magazine's inaugural issue.
Issue: June 1963
Mansfield's peek-a-boo cover is iconic—and not even her first appearance in the magazine. She was also Miss February 1955.
Issue: December 1979
Welch's tight red swimsuit might have kept her technically covered up, but was insanely sexy nonetheless.
Issue: January 1980
Yes, men can post for Playboy too—as comedian Steve Martin proved in 1980.
Issue: March 1980
Bo Derek has always been a perfect 10—so she was a natural fit for Playboy.
Issue: February 1983
Bassinger covered the February 1983 issue with flowing curls and sultry bedroom eyes that epitomized her sex appeal.
Issue: December 1983
Joan Collins was full Dynasty glam on her December 1983 Playboy cover.
Issue: January 1985
Goldie Hawn posing in a giant champagne glass? We'll toast to that any day.
Issue: September 1985
Madonna's Playboy cover line? "Unlike a virgin..." We see what you did there, Hef.
Issue: December 1986
Brooke Shields showed off her babydoll face and perfect pout on the December 1986 cover of Playboy.
Issue: May 1987
We'd like to buy a WOW for this Vanna White cover.
Issue: April 1988
Prince's protégé covered Playboy in April 1988 and May 1985.
Issue: July 1988
Cindy Crawford and her iconically sexy mole covered Playboy in July 1988.
La Toya Jackson
Issue: March 1989
LaToya Jackson was the epitome of rock star glam on her 1989 cover.
Issue: July 1990
Sharon Stone will do down in history as one of the biggest sex symbols in Hollywood history. Her 1990 Playboy cover illustrates why.
Issue: December 1990
Sherilyn Fenn's December 1990 cover mixed sexy and classy perfectly.
Issue: March 1994
Shannen Doherty has never done anything that wasn't unique and her doves-on-knees Playboy cover was no different.
Issue: May 1994
Elle Macpherson covered the May 1994 issue in nothing but a pair of black pantyhose. The cover, naturally, went down in Playboy history.
Issue: September 1994
The Head of the Class actress posed in nothing but a beaded choker in 1994.
Issue: November 1994
Pamela Anderson's brand of sex appeal was tailor-made for Playboy, as evidenced by her November 1994 cover.
Issue: January 1995
Drew Barrymore went meta for her cover shoot, donning a Playboy bunny shirt, a coy smile, and a lacy pair of pink panties.
Issue: December 1995
Farrah Fawcett proved she was most definitely ready for her close up with her December 1995 cover.
Issue: May 1998
Geri Halliwell was there to help Playboy readers spice up their lives in the May 1998 issue.
Issue: September 1998
Lisa Rinna made a slouchy sweater sexy as hell in the September 1998 issue.
Issue: May 1999
Even Oscar winners have covered Playboy. Case in point: Charlize Theron's May 1999 cover.
Issue: December 1999
Naomi Campbell was a barely-wrapped gift to the world on the December 1999 cover of Playboy.
Issue: May 2002
The original fitspo, Kiana Tom, covered Playboy in gold underwear in 2002.
Issue: November 2002
The OG Buffy the Vampire Slayer lit the November 2002 cover on fire with a fully-naked pose.
Dita Von Teese
Issue: December 2002
Burlesque queen Dita Von Teese went full pin-up for the December 2002 issue.
Issue: January 2003
Tia Carrere was a sultry, damp-haired goddess on the January 2003 cover.
Issue: November 2003
Splash star was the sexiest of mermaids on her November 2003 cover.
Issue: February 2004
Jaime Pressly's wet silk slip on the February 2004 cover looked painted on—in the sexiest way.
Issue: April 2004
Stacy's Mom herself, Rachel Hunter, wore a classic red teddy for her April 2004 cover.
Issue: June 2004
Buffy and Angel alum Charisma Carpenter was pure sex in her fully nude cover shot.
Issue: December 2004
Denise Richards was dripping in diamonds on her December 2004 cover.
Issue: January 2005
Jenny McCarthy went full bunny for her 2005 cover.
Issue: February 2005
Teri Polo wore nothing but a sheet accessorized with a single strawberry for her February 2005 cover.
Issue: March 2005
Paris Hilton wore the sexiest fishnets in the photo for her 2005 cover.
Issue: June 2005
Bai Ling was a sexy bondage lady for her cover shoot in 2005.
Issue: February 2007
Battlestar Galactica star Tricia Helfer's sexiness was out of this world on her February 2007 cover.
Issue: March 2007
Mariah Carey's tan cut-out one-piece was perfection on her March 2007 cover.
Issue: July 2007
The Olympian posed in nothing but bikini bottoms for the July 2007 issue.
Issue: August 2007
Garcelle Beauvais donned a sheer, multi-colored dress that looked like sexy, sexy body paint for her 2007 cover.
Issue: December 2007
Kim Kardashian took the world—and the cover of Playboy—by storm in 2007.
Issue: September 2008
The House Bunny star covered Playboy in September 2008 in a pink, two-piece ensemble.
Issue: January 2009
Carmen Electra's bedroom eyes took centerstage in her 2009 cover.
Issue: March 2009
Aubrey O'Day was all legs on her March 2009 Playboy cover.
Issue: July/August 2009
Olivia Munn was peak sexy geek in a red bikini on her summer 2009 cover.
Issue: September 2009
Heidi Montag got dirrrrty in a pure white bikini for her Playboy cover.
Issue: December 2009
Funny lady Chelsea Handler's December 2009 cover was definitely no laughing matter.
Issue: January/February 2010
Tara Reid took the smoky eye to the next level on her 2010 Playboy cover.
Issue: March 2011
Winter Zoli wore the sexiest pair of black lace panties for her cover.
Issue: April 2011
Taryn Manning's abs were as intense as her bangs and her black fishnets on her 2011 cover.
Issue: May 2011
Karina Smirnoff showed off her amazing dancer's bod on the May 2011 cover.
Issue: June 2011
Mick Jagger's daughter graced the cover of Playboy in 2011.
Issue: January/February 2012
Lindsay Lohan let her inner Mean Girl out for her 2012 turn on the cover of Playboy.
Issue: February 2014
Kate Moss donned the iconic Playboy bunny suit for the magazine's 60-year anniversary cover in 2014.
Issue: April 2015
Azealia Banks' colorful cover was as unique as she is.
Issue: September 2019
Travis Scott took Kylie Jenner's 2019 Playboy cover.