One of the most shocking celebrity couples in history that you probably weren't even aware of has to be Madonna and Tupac Shakur. Madonna herself revealed the fact in a 2015 appearance on the Howard Stern Show. And needless to say, it was quite a shock for everyone, and the tale of how the two hooked up is a pretty interesting one as well. It involved Shakur's friend, actor Rosie Perez's help to set the two up and even she recalled the fact with quite some pride and a smirk. Madonna revealed she was dating Tupac Shakur two decades after the

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