Chelsea Handler surprised the public when she appeared for the magazine's cover in 2010. Handler revealed her cover on an episode of Late Night with Jay Leno and shared how she was changing course in her career.

While it may be unusual to use Playboy as a chance to speak your goals and dreams, Handler took the opportunity to share she was having a change in course, using her comedic relief talk show for more good than dissing the likes of Kardashians and making fun of A-list celebs. Handler since has made a very successful political Netflix talk show, and proved her dreams were right on track!

Despite being one of the world's most recognized models in the 90s, Kate Moss wasn't actually featured in the magazine until 2013, and graced the cover for Playboys' 60th birthday edition!

The model went full bunny for the cover and was featured in an 18-page spread. In the spread, and done tastefully, it was one of the last issues that featured full nudity.