Megg’s Pleasure

Jay-Z Can’t Keep a Secret In 2003, the rap mogul managed to hide what was almost certainly a full-on relationship with Beyoncé during his Playboy Interview. Now, he can't keep his Super Bowl performance under wraps.

We Asked a Woman Comedian to Make Shane Gillis Jokes Madison Sinclair, famous for her roast comedy, joins Playboy for a bit of post-SNL fun.

The Playboy Interview: Mike Tyson In light of his new Netflix documentary, here's Mike Tyson's 1998 Playboy Interview.