Before Macy Gray was a Grammy Award-winning singer, she was a college student originally from Canton, Ohio, writing songs in a friend's dorm room "studio." Then, she was discovered by an executive at Atlantic Records during a performance and became an overnight sensation with her own record deal. After Gray's breakout song, "I Try," reached No. 1 on the Billboard charts in 2000, her album went triple platinum and landed her five Grammy nominations. She won for best female pop vocal performance.
The whirlwind of fame had quite an impact on the former small-town girl, as she recently told "Oprah: Where Are They Now?"