100. Lisa Loeb
Band Or Solo Artist?: Solo
Genre: Vocal Pop, Cabaret
Greatest Hit: "Stay (I Missed You)" 1994
The perfecter of nerd chic, Lisa Loeb nailed the hit “Stay (I Missed You)” in '94 and became the first artist to have a No. 1 single without being signed to a label. She’s the OG of the indie scene, encouraging more artists to succeed without corporate backing. As a testament to her sex appeal, her iconic cat-eyed glasses will remain a fashion staple forever.