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Diddy is not only a man of many names (Puff Daddy, Sean Combs, P. Diddy, etc.) but he is also a man of many talents. The multi-hyphenate star has proven his ability at rapping, producing, fashion design and more. His label Bad Boy helped to develop the careers of other stars including good friend The Notorious B.I.G. While Diddy has five kids, three of which are with ex-girlfriend Kim Porter, his most famous romantic tryst was with Jennifer Lopez, due in large part to the couple's ties with a club shooting in New York City.

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