Sean Combs
A hip-hop producer, rapper, fashion designer, TV producer, Broadway actor, entrepreneur, and all-around party boy, by the time you finish reading this, he'll likely have started a new business venture or given himself a new name.
Raised in New York City by his mother Diddy started his music career in 1993, at the age of 21, when he founded his own record label, Bad Boy Entertainment, along with childhood buddy the Notorious B.I.G. Over the next few years, Diddy signed a slew of artists while also writing and producing tracks for artists on other labels, and pursuing a music career of his own. In 1998, Combs branched out into clothing with his Sean John label; that same year he formed his first film/TV production company. In addition to about a dozen other side ventures in recent years ("Vote or Die" being one of many examples), Combs has also acted in about two dozen films. In 2004, he appeared on Broadway and then in the TV adaptation of Raisin in the Sun.
Combs' most high-profile romance was with Jennifer Lopez, with whom he was arrested on weapons charges in 1999. She dumped him in 2001. He has five children with almost as many ladies. [Image via Getty]