Men Madonna Has Dated

In the early 1990s, Madonna dated this former Calvin Klein underwear model. The pair mixed business with pleasure, as Tony appeared in some of her music videos and her 1992 soft-core coffee table book, Sex. She was also linked to another star of the book: Vanilla Ice. He said the book caused them to break up: "We were in a relationship yet it looked like she was screwing all these other people."