The 19 Most Iconic Playboy Covers of All Time

• Issue: December 1953

For Playboy's very first magazine they made the brilliant decision of tapping Marilyn Monroe for the cover, which is by far their most legendary. Why is that? Consider the year 1953. There was still a lot of taboo in regards to sexuality (in particular women's sexuality), and what was considered acceptable when it came to women's style and how much skin they showed. By the time 1953 rolled around, Monroe was one of Hollywood's top stars and almost single-handedly changing and challenging the narratives around what women "should" and "should not do."

On the flip side, Playboy already knew they were going to be controversial, so why not put somebody on the cover who's equally controversial? See? Brilliant. Now we're not saying that the Playboy magazine and brand as a whole wouldn't have become what they did had they not gotten Marilyn for that first cover, we're just saying that it made them start off with a bang.

• Issue: October 1971

And when it comes to groundbreaking moments, we have to acknowledge the second most iconic cover in the history of the magazine which is Darine Stern, the first Black model to ever grace the cover of Playboy by herself. While in 1971 there was still a ways to go as far inclusivity in the entertainment industry, Stern's cover is considered revolutionary because back then African American models and actresses weren't given that many opportunities to grace the cover of magazines. Stern broke down a lot of barriers with her Playboy cover, the impact of which still remains felt today.

• Issue: October 1977

In the 1970s, there were still many that held the notion of Playboy being "controversial", "classless," and this that and the third. There was this unspoken (and perhaps spoken) belief that if you posed for Playboy, you were "devaluing" yourself. With those notions in mind, we think it's safe to say that Barbara Streisand being on the cover of the October 1977 issue caught a lot of people who held those beliefs off guard. In fact, on the cover you can see the caption "What's a nice Jewish girl like me doing on the cover of Playboy?"

Streisand is another one credited with help shifting the narrative.

• Issue: October 1978

Mrs. Dolly Parton had the honors of gracing Playboy in October 1978, which has gone on to be deemed as one of the most iconic issues in the history of Playboy as she was the first country singer to ever be featured on the cover. Parton recreated the cover in 2021 for her husband's birthday, and has stated that she would like to be on the cover again in the future.

• Issue: December 1995

The fact that Farrah Fawcett's Playboy cover isn't talked about more is quite literally a travesty. While you could make the argument that the peak year's of Fawcett's career and popularity was in the mid-to-late 1970s, the fact remains that her 1995 Playboy cover was the best selling issue of the 1990s—a testament to her longevity and power.

• Issue: December 1999

Thee. Naomi Campbell. If by the year 1999 there were still doubts about the validity when it came to posing for Playboy, those doubts had no other choice than to be put to rest as Naomi is one of the greatest and most influential models in history. It is what it is.

• Issue: September 1985

Back when Madonna was in her "Like a Virgin" and "Material Girl" days, she showed the world that she was indeed very much about the bad girl life she spoke of in her songs when she appeared in the September 1985 issue of Playboy. The coolest thing about this cover is by far Madonna being dressed in 1980s punk rock attire. You can always count Madonna to go against the grain and be different, and this was definitely different.

• Issue: April 2003

You have to be a product of the 1990s and 2000s to fully understand the impact of Carmen Electra as she was (and still is) viewed as one of the sexiest actresses of that time period. Carmen Electra was the blonde bombshell, so a pairing with Playboy only made sense. Electra posed for the magazine on multiple occasions, but it's her April 2003 cover that stands out the most.

• Issue: October 1993

You probably had the same record scratch moment that we did upon seeing this. Yes, Jerry Seinfield appeared on the cover of Playboy next to a bunch of hot young models, and he's an absolute legend for not just appearing on the cover, but for also wearing a varsity jacket and the Air Jordan VII's.

• Issue: February 1994

Anna Nicole Smith is another one of those "you had to be there" moments when it comes to influential celebrities, and if you weren't there, then you have to do your research in order to fully understand (we—as in the author—falls into this category for transparency). Smith is one of the most popular celebs of all time, and the fascination with her life and career has continued to grow in the years since her untimely passing. This might be a controversial "take," but Anna Nicole Smith is something comparable to the 1990s version of Marilyn Monroe, and with her being named the 1993 Playmate of the Year, it was only right that she take on the February 1994 Valentine's Edition.

• Issue: December 2007

Now this is a moment that we actually did witness in real time. The Kardashians are a massive empire nowadays, but in 2007 their popularity was only just starting to rise. The behind the scenes footage of this photoshoot was documented on the very early episodes of Keeping up with the Kardashians, further adding to Kim's popularity of becoming the rising "It Girl" in Hollywood.

• Issue: January 1995

Before she was a Charlie's Angel, our girl Drew (Destiny's Child voice) appeared on the cover of the January 1995 Playboy Issue. The then 19-year-old who comes from a lineage of Hollywood greats and was in the beginning of her establishing her own legacy, caused quite a stir with this one.

• Issue: July 1992

Pamela Anderson. Another 1990s dreamgirl. If you haven't yet watched her documentary on Netflix, then you should probably do so if you want a better understanding of her career and what the zenith of her popularity was like. Anderson's 1992 cover was also a legendary moment for the Playboy brand for the reasons you'll understand if you were around during that time period and/or have watched her documentary.

• Issue: July 1988

Cindy Crawford for Playboy. Shot by the fantastic Herb Ritts. It was hard choosing between this and Crawford's February 1998 Playboy cover ten years later, but the simplicity of 1988 shoot combined with the fact that it was a headshot (which wasn't standard for Playboy covers) is what made this the winner in our book.

• Issue: November 2009

In November 2009, Playboy wanted to switch things up a bit when it came to their cover models. So who did they choose? Marge Simpson. Classic.

• Issue: February 2014

The resume and impact of Kate Moss simply cannot be put into a caption as even the word extensive is an understatement. Moss did it for all the "short girls" out there who were frequently told that they weren't tall enough for high fashion modeling, creating an all time great modeling career that is still very much going. So it was only right that she grace the cover of Playboy's 60th edition.

• Issue: January 2012

Lindsey Lohan shocked the world and showed everybody that she was truly all grown up when she posed for the January 2012 issue of the magazine. The sultry shoot was fiery and fierce as Lohan almost bared it all for the publication in a shoot that clearly remains one of her favorites as she's been known to post throwbacks from time to time on Instagram.

• Issue: December 1983

We're just going to leave this here with the great Joan Collins who celebrated her landmark 90th birthday on May 23rd. Collins posed for the magazine for the December 1983 issue in a statement that very much gave "50 is the new 30" in the most epic way possible.

• Issue: February 1991

Yes we're doing Pamela Anderson again because...why not? Not only does Anderson have the most cover appearances with fourteen, but each and every cover she appeared on made waves at the time of its release—including this February 1991 issue that was just in time for Valentine's Day.