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The 41st Annual GRAMMY Awards

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In the late 1990s, Ms. Lauryn Hill found herself at a very transformative point in her life and career.

The Fugees were on an indefinite hiatus, she found love with Rohan Marley, and she was pregnant with her first child, Zion. As she was coming into her own as a woman, she was also doing so as an artist. These were some of the circumstances that resulted in the creation of her landmark solo effort, The Miseducation of Lauryn Hill. 

Released in August 1998, the album sent shockwaves throughout the music community. With elements of Soul, Hip-Hop and Reggae, tracks like “Lost Ones,” “Everything Is Everything,” “Ex-Factor,” and the #1 hit “Doo Wop (That Thing)” helped the project set an unprecedented bar that very few have reached since.

This was more than just an album. This was Hill’s declaration of independence, standing firmly in her creative fluidity. And she was handsomely rewarded for it.

In February 1999, at the 41st Grammy Awards, Hill came in with 10 nominations, a first for any female artist. She ended up winning five awards, including Best New Artist, Best R&B Album, and both Best R&B Song & Best Female R&B Vocal Performance for “Doo Wop (That Thing).”

The fifth and final award would land Hill in the history books, as she became the first Hip-Hop artist to ever win Album Of The Year. In an industry where many are still having a tough time acknowledging the genre as a legit artform, Hill broke a glass ceiling as a Black woman in a male-dominated genre.

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To put her wins into greater context, consider these facts:

  • Miseducation is only the third (and so far, last) album by a Black woman to win Album of The Year, following Natalie Cole’s Unforgettable…With Love (1992) and Whitney Houston’s The Bodyguard Soundtrack (1994).
  • Hill is the first to win five Grammys in one night, breaking Carole King’s record from 1971.
  • Hill is the first woman (and third artist overall) to win both AOTY and Best New Artist in the same year. (Norah Jones and Billie Eilish would follow in 2003 and 2020, respectively.)
  • Only one other Hip-Hop album would win after Hill’s: OutKast’s Speakerboxxx/The Love Below in 2004.

Overall, Hill would nab a career total of 19 Grammy nominations and 8 wins. Although she would never release a proper follow-up, she didn’t need to.

In very rare cases, all it takes is one masterpiece to get your point across and cement your place in the lexicon of music. For Ms. Lauryn Hill, The Miseducation was that masterpiece.