Lauryn Hill Wins 5 Grammys on This Date in Black History by Renee Gardner February 24, 2012 Renee Gardner Lauryn Hill, hip-hop and R&B diva, won five Grammy Awards-the most ever by a woman-on this date in 1999. Hill, whose debut solo album was entitled The Miseducation of Lauryn Hill, received ten awards nominations. Tags Black History Moment Grammy Awards Lauryn Hill R&B The Miseducation Of Lauryn Hill