Which artist became the first woman to win five Grammy Awards in one night?

Lauryn Hill became the first woman to win five Grammy Awards in one night.

Hill achieved the feat at the 41st Grammy Awards in 1999, when The Miseducation of Lauryn Hill won Album of the Year. She also won Best New Artist, Best R&B Album, Best Female R&B Vocal Performance for “Doo Wop (That Thing),” and Best R&B Song as a writer of the same track.

Her five-award night was a landmark for hip-hop and for women in the recording industry. The album combined rap with soul, R&B, reggae, and live-band arrangements, helping it reach audiences far beyond hip-hop’s traditional market.

This record should not be confused with the overall single-night record, which has been tied by several artists. Hill’s distinction specifically concerns being the first woman to reach five wins during one Grammy ceremony.