With his languid flow and pin-up looks, this Puff Daddy protégé quickly became one of hip-hop's brightest stars after dropping his debut album Harlem World in '97. Though he later took a more than a decade off between his third and fourth albums, his many guest-starring features and verses—with the likes of Notorious B.I.G., Brandy and Cam'ron—have cemented his legacy in the rap world.