With a then-record ten nominations, Lauryn Hill went into the 41st Grammy Awards (1999) a favorite to win big. By the end of the night, Hill won five, and set a record for most wins by a female artist in a single night. In addition to scoring Best New Artist, she won Best R&B Song and Best Female R&B Vocal Performance for “Doo Wop (That Thing),” and The Miseducation of Lauryn Hill won Best R&B Album and Album of the Year, making it the first hip-hop album to win in the category.
The singer-rapper capped off a record-making night with a performance of “Zion,” an ode to her first-born son, accompanied by Carlos Santana on guitar. Over the years, her record five wins would be tied by the likes of Alicia Keys (2002), Norah Jones (2003), Beyoncé (2004), Amy Winehouse (2008), and Alison Krauss in 2009. The record was broken in 2010 by Beyoncé, who won six.
Nearly two decades after its release, The Miseducation of Lauryn Hill still stands as one of the greatest albums of all time. Unlike anything before or after it, the album’s lasting impact on music and pop culture is proof that music has no expiration date.
Watch Lauryn Hill perform “Zion” with Carlos Santana below.
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