Aaliyah, 22 Years Old
R&B icon was only 22 when she died in a plane crash. She was just 10 when she performed alongside Gladys Knight, and by 12 she'd earned a record deal. She worked with artists like Missy Elliot and Timbaland and R. Kelly while she was at her prime. She was illegally married to Kelly because she was sixteen at the time, and eventually disputed the marriage. Her death was a tragedy for the entire industry.