Lisa Loeb

The bespectacled Lisa Loeb became every English major's dream date when "Stay," a single from the movie Reality Bites, made her the first unsigned artist to have a No. 1 hit single. She didn't remain without a label for long, and the Adult Alternative Folk-Rocker has since released two solid albums and had a moderate follow-up hit with "I Do." Loeb's catchy tunes are more grounded than Suzanne Vega's, but come across as more idiosyncratic and personal than Sheryl Crow's.