Lauryn Hill Wins Five of 10 Nominations at 1999 Grammy Awards

For Black History Month this year, Rémy Martin teams up with XXL to celebrate 10 important moments in hip-hop history. Through the years, Rémy Martin has created a synonymous relationship between cognac and music culture by representing celebration and entertainment seamlessly. In honor of hip-hop’s nearly 50-year existence, host DJ Suss One, XXL Awards Board members Kendell “Sav” Freeman, Vice President/Co-Head of Urban Music at Arista Records; Sydney Margetson, Senior Vice President of Publicity at Atlantic Records; and Traci Adams, Executive Vice President of Promotion at Epic Records, revisit Lauryn Hill winning five Grammys out of the 10 she was nominated for at the 1999 Grammy Awards as a monumental milestone in the genre.

At the 1999 Grammy Awards, Lauryn Hill was the X-factor, bringing home five awards in record-setting fashion as a result of her debut solo album, The Miseducation of Lauryn Hill, released on Aug. 25, 1998. The Fugees member was nominated for a whopping 10 awards at the 41st rendition of the awards show, which aired on Feb. 24, 1999. The lyricist and songbird went five for 10, taking home golden gramophones for Album of the Year, Best R&B Album, Best New Artist, and Best R&B Song and Best Female R&B Vocal Performance for “Doo Wop (That Thing).”

“This is crazy because this is hip-hop music,” Hill said during her acceptance speech for Album of the Year, for which she was up against Madonna (Ray of Light), Sheryl Crow (The Globe Session), Garbage (Version 2.0) and Shania Twain (Come on Over).

The big night was a precedent-setting one for hip-hop as it was the first time a hip-hop-R&B act had taken home the Album of the Year honor. The five wins also made Hill the first female artist to be awarded five Grammys in one year, surpassing the four awards singer Carole King won for her Tapestry album 27 years prior in 1971. ’Til this day, Hill is only one of two hip-hop acts to win the Album of the Year Grammy, with the other being OutKast, who won the award for Speakerboxxx/The Love Below in 2004. To date, Hill has 19 nominations and eight total wins. The reclusive singer never followed up her debut album. But that night, back in 1999, she had that thing.

Important milestones in hip-hop like this deserve recognition for years to come. As part of Black History Month, Rémy Martin and XXL will be making a donation to Black Music Action Coalition, an advocacy organization that was formed to addresses systemic racism within the music industry and reaches racial justice throughout society at large. Rémy Martin and XXL will match every additional dollar donated to BMAC during Black History Month.*

Watch DJ Suss One, Kendell “Sav” Freeman, Sydney Margetson and Traci Adams discuss Lauryn Hill’s Grammy takeover below.

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*Rémy Martin to match donations up to $50K, XXL to match donations up to $10K.