Lisa Loeb

What she’s been up to: Although she never emulated the success of her first single “Stay (I Missed You),” Loeb is not a one hit wonder. She had numerous hits in the ‘90s as well as two gold albums. However, throughout the aughts Loeb stopped making mainstream music and opted to make children’s music. In 2006, she starred in an E! reality show about her dating life called Number 1 Single and in 2010, she cashed in on her signature look by starting the Lisa Loeb Eyewear Collection.

Why YMCMB should sign her: Turn the radio on and turn the radio up and all you hear is Young Money artists singing their songs. Clearly, they’ve cornered the market. Now they need to corner the hipster market which is too cool to listen to radio.

Complex says: Just look at the glasses! Lisa Loeb is obviously the Original Gangster Hipster. We’d bet there’s at least 15 girls in Williamsburg ironically dressed up as Lisa Loeb right now.