Sean "Diddy" Combs
A talented producer who introduced such best-selling hip-hop artists as Lil' Kim and The Notorious B. I.G., Sean "Puff Daddy/Puffy/P.Diddy/Diddy" Combs transformed himself from a sharp business mogul into a top recording artist and talented actor. After becoming the youngest executive at Uptown Records when he was just 19, Combs jumpstarted numerous fledgling careers, only to be summarily fired due to internal power struggles. He soon formed his own company, Bad Boy Entertainment, which became responsible for launching the career of Notorious B.I.G., a.k.a. Biggie Smalls, widely considered to be the greatest rapper of all time. But tragedy struck when Biggie was gunned down in a drive-by, leaving Bad Boy without its top-selling artist and Combs without his close friend. Combs paid tribute to his fallen friend with the hit single, "I'll Be Missing You" (1997), which also ushered in his career as a recording artist. Combs entered into other entrepreneurial ventures like opening the soul food restaurant Justin's and starting the very successful Sean John clothing line. When he seemed to reach new heights, however, Combs ran into serious legal trouble that threatened to derail not only his career, but his very freedom following a shootout at a nightclub that lead to criminal weapons charges. With his then girlfriend Jennifer Lopez at his side, Combs managed to beat the high-profile wrap, though some in his entourage were not so fortunate. Nonetheless, he continued advancing himself, becoming an executive producer of the MTV series "Making the Band" and "I Want to Work for Diddy" (VH1, 2008-10), while demonstrating his acting bona fides in "Monsters Ball" (2001) and "A Raisin in the Sun" (ABC, 2008), all of which confirmed his status as a multi-faceted and self-taught talent who never failed to surprise fans.