The long list of men Madonna has slept with – this will shock you! (With Pictures)

6.  Vanilla Ice

Robert Van Winkle, AKA Vanilla Ice was one of Madonna’s many men, believe it or not. They dated briefly in the early 1990s, and Ice claims that Madonna was quite the exciting “older lover.” As exciting as the relationship may have been, the duo broke up after she released her Sex book. Perhaps Ice wasn’t so keen on such a hot publication, being “Ice” and all. Regardless of the reason for the split, it was evident that this romance wasn’t going to last. Ice is a one hit wonder and Madonna is a mega-star. Plus, with his prudish ways in regard to her Sex book, Ice may have been a little too “Vanilla” in the bedroom department for a wild child like Madonna. Although, it would have been fun if the two recorded a song together. Yet, Madonna did record “Frozen” in 1998 (perhaps that was an ode to her ex, Vanilla Ice)!