1. Madonna and Tupac
Via blkdmnds.com
Two of the most legendary musicians had collaborated in the past, and not in a music way, but in a romantic way. In an interview with Howard Stern on his SiriusXM radio show, Madonna revealed she had dated rapper, Tupac Shakur, just three years before he was murdered in 1996. According to the “Material Girl” singer, the two were introduced by actress, Rosie Perez, at the 1993 Soul Train Music Awards in Los Angeles. From there, the pair hit it off and began to date seriously. Madonna had told Stern that during her interview with David Letterman on The Late Show, the “California Love” rapper got her “all riled up about life in general” which is why she was noticeably cussing a lot during the show.
Perez also opened about the musicians’ relationship during The Wendy Williams Show and confirmed the rumors surrounding the pair. The actress also confessed on The View that it was Madonna who came up to her to ask to be introduced to the “Thug Life” rapper and so, Perez did and admitted she was happy that she did it. Lucy O’Brien got involved with the relationship, too, in her 2007 unauthorized book, Like An Icon, discussing that the “Vogue” singer was serious about her relationship with the hit-making rapper that she eventually wanted to start a family with him. To this day though, Madonna remains hush-hush about her relationship with Shakur, who was shot and killed in 1996. The pair did make an eye-catching couple so we could imagine all the attention they would be getting if they were still dating. They would probably be a better version of “Kimye” today.
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