The man of many monikers — Puff Daddy, P. Diddy, Puffy, etc — has made a name for himself in multiple industries. He got started on his journey to mogul as a 12 year old who lied about his age to get a paper route and then created several false identities in order to operate several others simultaneously. He studied business administration for two years at Howard before taking an internship at Uptown Records. Four years later and two weeks after being fired from the label, he formed Bad Boy Records and produced the debut of the legendary Brooklyn rapper The Notorious B.I.G. He helped launch the careers of Mary J. Blige, Jodeci, Lil' Kim, Faith Evans and himself. Diddy's tribute to his slain friend Biggie, "I'll Be Missing You," helped make his debut album, No Way Out, multi-platinum. The runaway success lead to lavish and legendary parties with strict dress codes, dating Jennifer Lopez, forays into acting (Monster's Ball, Get Him To The Greek, A Raisin In The Sun on Broadway), founding the Vote or Die campaign and producing reality TV series like Making the Band and Run's House. In 1998, he took on the fashion world. Sean Jean started with clothes for men and boys but expanded to include women's and fragrances by 2004. He's even in the beverage industry as brand ambassador for Ciroc vodka. It's amazing he found time to father five kids with three women — sons Justin and Christian, daughter Chance and twins D'Lila and Jessie.