Lauryn Hill Wins Five Grammy Awards in 1999 – Today in Hip-Hop

XXL celebrates 50 years of hip-hop with this moment:

Feb. 24, 1999: On this day, at the 41st Annual Grammy Awards ceremony, Lauryn Hill made history by winning five Grammy Awards and becoming the first hip-hop artist to win Album of the Year. Additionally, Ms. Hill also became the first female solo artist to win five awards in one night.

L-Boogie’s debut solo album, The Miseducation of Lauryn Hill, took home golden gramophones for Album of the Year, Best New Artist, Best Female R&B Vocal Performance, Best R&B Song and Best R&B Album. Hill beat some music industry heavyweights that night, such as Madonna (who won three awards), the Dixie Chicks, Shania Twain, the Backstreet Boys, Sheryl Crow, Celine Dion, Aaliyah, Erykah Badu, Janet Jackson and Aretha Franklin. Yet, Hill’s personal debut proved that it was her night to make history.

The South Orange, N.J. native began her career with the Grammy Award-winning group the Fugees, whose hits include “Killing Me Softly” and “Ready or Not.” However, the rap trio went their separate ways in 1998, following some tension that had built up between Lauryn and bandmate, Wyclef Jean. Life experiences and a new solo start gave Lauryn everything she needed to pour her heart into Miseducation.

Her most personal project to date, The Miseducation of Lauryn Hill detailed all of Hill’s struggles, from motherhood and loss to spirituality and relationship strife. In making this album, Lauryn spoke to young women everywhere and shared messages that still resonate today.

On Feb. 17, 2021, Lauryn Hill celebrated another milestone: Miseducation was certified diamond (10 million sold) by the Recording Industry Association of America (RIAA).

Watch Lauryn Hill Win Album Of The Year at 1999 Grammy Awards Below

Watch Lauryn Hill and Carlos Santana Perform “To Zion” at 1999 Grammy Awards Below

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