Year won: 1999
Was she cursed? This is an especially tough one, but we have to admit that yes, Lauryn Hill's career was cursed. After she took home the best new artist award — one of five Grammys she nabbed that year — she dropped out of the public eye due to dissatisfaction with the music industry and an overall indifference to fame. Since then, Hill has released a few songs and done a few festival appearances, but her erratic behavior has made fans skeptical of a proper comeback. In 2012, she pleaded guilty to charges of tax evasion and served a three-month prison stint. In 2022, she planned to embark on a reunion tour with the Fugees, but it was ultimately canceled. Yes, we'll always have "Doo Wop (That Thing)" and "Ex-Factor," but we're still holding out hope that Hill will have a full musical resurgence.
