1. Will Smith
There’s no question that Will Smith is the most successful rapper-turned-actor. In fact, Will Smith might be the most popular actor on the planet. A member of the elusive $20-million-a-movie club, Will Smith first became known as the rapping half of DJ Jazzy Jeff and the Fresh Prince. His first major role was on The Fresh Prince of Bel-Air on which Smith played a comedic version of himself. Years down the line, he’d end up snagging two nominations for Best Performance by an Actor in a Leading Role for his work in 2002’s Ali and 2007’s The Pursuit of Happyness.