The Chicago native has been subverting the music industry’s traditional business model since he was a teenager, declining to sign with a major label and instead releasing his own streaming-only mixtapes, featuring unique strains of hip-hop splashed with sunny spirituality. Last year, he won the first-ever Grammys (three of them) for a streaming-only album and received $500,000 to debut the tracks exclusively on Apple Music. He’s also a celeb endorser for Nestle, Nike, and even Twitter. Up next: He’s set to star in the movie Slice as a pizza-delivery driver/werewolf.