On May 3 1991, Madonna appeared on the cover of The New York Post with the headline, “What A Tramp!” The article focused on Madonna’s Truth Or Dare documentary. In the article, Ray Kerrison called Madonna, “vulgar” and the “degenerate queen of sleaze.”

Jay’s Note: I bet Ray Kerrison had no idea that this particular cover of The New York Post would become one of the most sought after and iconic covers of all-time. You could write just about anything alongside this image from the Justify My Love single cover and it would still be beautiful.