Ray J

Ray J has worn many hats over the years. He was signed to Elektra in 1995, when he was only 14, and released his debut album, Everything You Want in 1997. But he soon pivoted, starring alongside his real-life sister Brandy on the hit UPN show Moesha. By the time he returned to music following the show's last episode in 2001, he was faced with a far different marketplace. He adjusted, switching from saccharine pop to a more hip-hop style on This Ain't a Game, which found him rapping over beats from the Neptunes. The album was a commercial failure, and though its follow-up, 2005's independently released Raydiation, was moderately more successful, Ray would soon become known as the dude in Kim Kardashian's sex tape. The video was a runaway success, propelling Kardashian into the upper echelons of celebrity. It also provided good publicity for Ray, and he once again scored big with the hit "Sexy Can I."