13. Took Her Boyfriend To The Oscars...Her Boyfriend Was Michael Jackson
Remember that time Madonna and Michael Jackson dated? Probably not, as this whirlwind romance was doomed for the word go. Her aim throughout her career has been to keep people talking and to continue to shock the world, which is why choosing to take the King of Pop to the awards ceremony as her date was more a professional choice than a personal one. With her previous squeezes including Warren Beatty, John Kennedy Jr, Vanilla Ice and Dennis Rodman; its hard to find someone famous Madonna hasnt been linked to.