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Naturally, Combs and his girlfriend, Cassie, were dressed to the nines for the occasion, twinning in glamorous party ensembles.

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He had his first son in 1993 with designer Misa Hylton-Brim, his high school sweetheart.

In 1998, his second son was born in 1998 with his on-again-off-again girlfriend Kim Porter.

Sean “Puff Daddy” Combs started his career as the founder of Bad Boy Records in 1993, which went on to sign rap icon Notorious B. That was just the beginning for this aspiring businessman.

In 1998, Sean “Puff Daddy” Combs launched his award-winning clothing line, Sean John, and in 2001, he made his acting debut in the film Made with Jon Favreau and Vince Vaughn, followed by the drama Monster’s Ball alongside Halle Berry and Billy Bob Thornton.

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