With ‘Playboy’s’ recent announcement that they would stop featuring nudity inside their pages, we explore the covers that helped catapult the magazine to millions of sales each month.

For a generation of young men, Playboy was often their very first glimpse at the completely nude female form. Whether it was the inaugural cover in 1953 that featured Marilyn Monroe and a legendary photo that threatened her burgeoning film career, to Carmen Electra’s multiple appearances in a more contemporary context, the publication and the term “sex appeal” became synonymous with one another.

With the recent announcement that Playboy would discontinue their usage of nudity due to a number of contemporary factors – like the ease at which a person can seek out similar material for free using the Internet – the 62-year-old company is now positioning itself as a rival of VICE, with a spokesman cracking, “The difference between us and VICE, is that we’re going after the guy with a job.”

While the Playboy brand has certainly had success with other “in-magazine” features like interviews with Martin Luther King, Jr., and fiction from the likes of Norma Mailer, Gabriel Garcia Marquez, Nadine Gordimer and Ray Bradbury, the magazine will forever be remembered for launching starlets and undressing Hollywood heavyweights.

From bucking cultural norms to outright war, here are five Playboy covers that should never be forgotten.

Darine Stern

Playboy’s progressive attitude as it related to perceptions of beauty at a time when race relations still had fresh wounds from the Civil Rights Movement can’t be ignored. After 18 years in circulation, Playboy finally featured an African-American model, Darine Stern, front and center for their October 1971 issue. Although there was no accompanying pictorial, it remains a real moment that should forever be ingrained in the minds of pop culture enthusiasts.

The cover’s design saw newfound interest when Marge Simpson graced the cover in November 2009 – posing in an almost identical position as Stern.

Patricia Margot McClain

When Bob Guccione‘s Penthouse emerged on the print scene in 1969, it proved to be the first major challenger to Hugh Hefner’s T&A empire.

While Playboy had always attempted to portray an image of a “classier gentleman,” Penthouse raised the stakes and bucked moral trends at the time with photoshoots and editorials that were far more sensational and explicit. This set the stage for a back-and-forth game of one-upmanship between the publications that was deemed, “The Pubic Wars.”

Coined by Hugh Hefner himself, it referred to his stance on nudity that it wasn’t pornographic if the photos didn’t depict pubic hair or genitals.

For Playboy’s November 1975 cover, they featured model Patricia McClain slipping her hands into her underwear – seemingly reverting/stooping to Penthouse’s aesthetics.

According to the book, Mr. Playboy: Hugh Hefner and the American Dream, publications like Newsweek described the cover by stating, “to give her the benefit of the doubt, [she] seems to be plumbing the depths of her bikini panties for a stray kernel of popcorn.”

In turn, Playboy’s director of advertising, Howard Lederer, scolded Hugh Hefner and warned him that the company stood to lose $40 million USD in advertising because of the racier content. Hefner eventually realized that the cover was a mistake and traced his steps back to a line that he would never cross again.

Cindy Crawford

Although her name will forever be synonymous with the word “supermodel,” there was a time when Cindy Crawford was an upstart actress looking to make a splash in Hollywood.

One year after appearing in the opening credits for the Michael J. Fox film, The Secret of My Success, Crawford graced the cover of Playboy in July, 1988.

Shot by renowned celebrity photographer Herb Ritts – who along with peers Robert Mapplethorpe and Bruce Weber – completely reinvented the way that the general public viewed nude photography by upping the artistry in their compositions.

In speaking with The Wall Street Journal about her working relationship with Ritts, Crawford said, “I did Playboy with Herb two times. People have asked me, ‘would you do Playboy [again]?’ Besides the fact that I have a 12-year-old son now, I trusted Herb so much. He and I did pictures that we thought we liked and then sent them to Playboy. ‘We’re going to do what makes us happy, we’re not going to do Playboy pictures, we’re doing beautiful nudes, and if you guys like them, then great.’ There are very few people I would feel that comfortable with and protected.”

Pamela Anderson

In October 1989, Pamela Anderson would appear for the first time on the cover of Playboy after being discovered at a British Columbia Lions football game in Vancouver which led to her becoming the “Blue Zone” girl for Labatt’s beer.

Although she has a record 13 covers under her belt, the first really captured the public’s attention thanks to the collegiate spin – a tried-and-true formula for the magazine who over the years have explored the racier side of law enforcement, politics and finance.

Kim Kardashian West

Believe it or not, there was a time when we wanted more Kim Kardashian. In December of 2007 – years before she became one of the biggest power couples in Hollywood after tying the knot with Kanye West – Kardashian was still a relative unknown to many people as her popular E! series Keeping Up with the Kardashians wasn’t even a blip on people’s radar yet.

Seen as more of a debutante than a mogul, Kardashian turned to Playboy to elevate her profile and provide a juicy storyline for the families reality show. Like it or not, this cover provided the first stepping stone in many for Kardashian West in her attempt “to be famous for being famous.”

Words by Alec Banks
Features Editor

Alec Banks is a Los Angeles-based long-form writer with over a decade of experience covering fashion, music, sports, and culture.