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Lauryn Hill's 'The Miseducation of Lauryn Hill' wins Grammy Album of the Year

At the 41st Annual Grammy Awards, Lauryn Hill — six months after the Ruffhouse / Columbia release of *The Miseducation of Lauryn Hill* — wins Album of the Year, becoming the first hip-hop artist to win the Grammys' top all-genre prize. She takes home five Grammys total: Album of the Year, Best New Artist, Best Female R&B Vocal Performance, Best R&B Album, and Best R&B Song ('Doo Wop (That Thing)').

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Why it matters

The 1999 ceremony marks the moment the Recording Academy — historically conservative on hip-hop — credentials a hip-hop LP as the best album of any kind released in a calendar year. It will be 25 years before another hip-hop LP wins AOTY (no rap album wins it again until well into the 2010s; Cardi B's *Invasion of Privacy* wins Best Rap Album in 2019 as a separate milestone). Hill's five-Grammy night is also the largest single-ceremony Grammy haul by a hip-hop artist for nearly a decade.

Branches

Tags: lauryn-hillmiseducationgrammysaoty1999

Citations 3

  1. A
    Recording Academy — 41st Annual Grammy Awards — winners list Retrieved 2026-05-24.
  2. B
    Wikipedia — 41st Annual Grammy Awards Retrieved 2026-05-24.
  3. B
    Wikipedia — The Miseducation of Lauryn Hill Retrieved 2026-05-24.

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