Lauryn Hill at the 1999 Grammy Awards. She was the first rapper to ever win 'Album of The Year' for her one and only album ever, The Miseducation of Lauryn Hill. She is also the last black female artist to win the award since. That night she set the record for most nominations for a female artist in one night, broke the record at the time for the most wins by a female artist in one night, and became the first female rapper to win the Best New Artist award. She also won Best R&B Album, and for her song "Doo Wop (That Thing)" she won Best R&B Song and Best Female R&B Vocal Performance. This woman is a true legend.
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