Lisa Loeb

If you thought getting in the charts was difficult for signed artists, can you imagine how much harder it must be for those who work independently? Yet, this was the achievement Lisa Loeb managed to accomplish back in the 90s. She was the first singer to do so and it’s all thanks to her hit song, Stay (I Missed You), which is a platinum-selling number 1 hit song. On top of topping the charts, the song was also featured in one of the decade’s most iconic films, Reality Bites.

This immediately gave her a degree of mainstream success and her follow-up tracks did not disappoint. Her studio albums include two back-to-back albums, both of which won gold medals. Aside from having a successful music career, Loeb is also an actress and does voice-over work. She even had guest-starring roles in the Gossip Girl season finale! Until today, she continues to work on songs and fans are hoping that she will release them soon.