Adam Levine
Everyone loves early Maroon 5. "She Will Be Loved" is one of their biggest hits of all time, and Levine even earned some Grammys back in the day. However, pretty much all of their recent releases sound the same. Sure, he's an industry titan, but he's also a little annoying.
Rihanna
Rihanna is an industry mogul who knows how to merchandise fashion and cosmetics, but where she falls flat, ironically enough, is in her music career. Though she had early hits like "Umbrella," she hasn't put out music in several years and nobody has seemed to really notice.