On Grammy night in 1999, Lauryn Hill walked away with the Album of the Year award for 'The Miseducation of Lauryn Hill,' as well as four other shiny gramophones for her work -- a total of five.

‘The Miseducation’ was a diary of songs on love, heartbreak, redemption and the view of the world from a young woman’s perspective. ‘Doo Wop (That Thing)’ became a No. 1 hit single and won her an award for Best R&B Female Vocal Performance and Best R&B song.

Overall, the album garnered 10 nominations at the 41st Grammy Awards. With her five wins, it made Hill the first female recording artist to receive that number of nominations, as well as awards won in one night.

 
 

Watch Lauryn Hill's 'Doo-Wop (That Thing)' Video