7. Kelly Osbourne
Kelly Osbourne covered Madonna’s hit song “Papa Don’t Preach,” which many thought was a landmark move since Madonna is fiercely protective of her work. Years later, Osbourne promoted Madonna’s Material Girl fashion line. All of this synergy sparked a debate about whether or not Madonna and Osbourne hooked up.
Since Madonna has such a long list of conquests, the odds probably favor that they did. Plus, Osbourne has been suspected of being bisexual for years, and she fits in with Madonna’s type of hooking up with ladies with short hair. Now that Sharon Osbourne has disclosed that she is bisexual, many are thinking that the apple doesn’t fall far from the tree. Pictured with Lourdes, Madonna’s daughter, on the left.
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