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?