Playboy has been the home of its fair share of watershed moments in culture and has hosted more than its fair share of badass women through the years, so take a long lunch and doodle in some coloring pages of some of the biggest moments in Playmate history.

Marilyn Monroe – 1953
It wouldn’t be a Playboy retrospective without our first cover girl and the subject of more attention and misattributed quotes than nearly anyone in history. Thanks, girl.

Darine Stern – 1970
Stern changed the game as the first black Playmate to appear on the cover by herself. Following this cover, she had a successful modeling career with Ford.
Julie Peterson – 1987
Peterson was featured in a steamy spread in the winter of 1983 and joined MENSA in the 1990s, so it’s a matter of time before the world takeover.
Pam Anderson – 2001
This cover is by no means Anderson’s first – she holds the record for most Playboy covers, clocking in at thirteen between 1989 and 2016, when she was the cover girl for our final nude issue. Here she is, on fire as usual.
Kim Kardashian – 2007
There’s no doubt in my mind that Kim Kardashian is one of the twenty-first century’s foremost marketing gurus and evil geniuses, as evidenced by her breakthrough Playboy cover capitalizing on the early success of Keeping Up with the Kardashians, which debuted the same year.
Sarah McDaniel – 2016
And finally, the first non-nude cover girl who can go joke for joke with Stephen Colbert and gives Kim a run for her money as the reigning queen of the selfie.