41st Annual Grammy Awards

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41st Annual Grammy Awards
DateFebruary 24, 1999
LocationShrine Auditorium, Los Angeles
Hosted byRosie O'Donnell
Most awardsLauryn Hill (5)
Most nominationsLauryn Hill (10)
Television/radio coverage
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The 41st Annual Grammy Awards were held on February 24, 1999, at Shrine Auditorium, Los Angeles. They recognized accomplishments by musicians from the year 1998. Lauryn Hill received the most nominations with 10, setting a record for the most nominations for female artist in one night.[1] During the ceremony, Hill became the first woman to receive 5 Grammy Awards in a single night, and the first woman rapper to take home Best New Artist.[2] Her album The Miseducation of Lauryn Hill became the first hip hop album to win the award for Album of the Year.[3] Hill's Grammys sweep is widely considered as one of the biggest moments in hip hop history.[4]

Songwriters James Horner and Will Jennings won Song of the Year for Celine Dion's "My Heart Will Go On". Dion herself took home Record of the Year for the latter song.[5] The ceremony was known as the "Grammy Year of Women", because every artist nominated for Album of the Year was female (including Garbage, with Shirley Manson as the lead singer).[6][7]

Madonna won three awards and opened the show with her performance of "Nothing Really Matters".[8] While musicians the Dixie Chicks, Vince Gill, Alanis Morissette, Stevie Wonder and Shania Twain won two apiece.[9][10][11] It is widely remembered for Ricky Martin's performance of "La Copa De La Vida"/ "The Cup of Life".[12]



Award winners[edit]


Record of the Year
Album of the Year
Song of the Year
Best New Artist


Best Alternative Music Performance




  • From 1994 through 2003, see "Best Spoken Comedy Album" under the "Spoken" field, below.


Composing and arranging[edit]







Musical show[edit]

Music video[edit]

New Age[edit]

Packaging and notes[edit]



Production and engineering[edit]


Best Female R&B Vocal Performance
Best Male R&B Vocal Performance
Best R&B Performance by a Duo or Group with Vocal
Best R&B Song
Best R&B Album
Best Traditional R&B Vocal Album


Best Rap Solo Performance
Best Rap Performance by a Duo or Group
Best Rap Album




Traditional pop[edit]


Special merit awards[edit]

MusiCares Person of the Year[edit]

Grammy Legend Award[edit]


  1. ^ "Most Grammy nominations in a single year for a female artist". Guinness World Records. Retrieved 2022-06-15.
  2. ^ "First female rapper to win Best New Artist at the Grammys". Guinness World Records. Retrieved 2022-06-15.
  3. ^ II, C. Vernon Coleman IIC Vernon Coleman. "Lauryn Hill Wins Five of 10 Nominations at 1999 Grammy Awards - Hip-Hop's Biggest Milestones in Music History". XXL Mag. Retrieved 2022-06-15.
  4. ^ "25 Moments That Moved Hip Hop Culture Forward". BET. Retrieved 2023-08-20. * Kamer, Foster. "The 40 Biggest Hip-Hop Moments in Pop Culture History". Complex. Retrieved 2023-08-20. * "The 50 greatest moments in hip-hop history". Yahoo Entertainment. 2023-08-07. Retrieved 2023-08-20. * "Hip-hop moments that shook the world". The Independent. 2011-08-06. Retrieved 2023-08-20. * "50 defining moments in hip hop history to mark hip hop's 50th anniversary". New York Daily News. 2023-08-09. Retrieved 2023-08-20. * Grein, Paul (2023-02-02). "31 Milestones in Hip-Hop Awards History: Star-Studded Grammy Salute, Super Bowl Halftime Show & More". Billboard. Retrieved 2023-08-20.
  5. ^ Strauss, Neil (1999-02-25). "5 Grammys to Lauryn Hill; 3 to Madonna". The New York Times. ISSN 0362-4331. Retrieved 2022-06-15.
  6. ^ "Shirley Manson on the Groundbreaking 1999 Grammys: 'Nonconformist Women Were Getting a Moment'". Billboard. 2018-10-11. Retrieved 2022-06-15.
  7. ^ "Grammys Flashback: Twenty Years Ago, Women Ruled the Awards". Billboard. 2018-10-11. Retrieved 2022-06-15.
  8. ^ "1999 Grammys fashion flashback". Wonderwall.com. 2019-01-07. Retrieved 2022-06-15.
  9. ^ "CNN - That thing: Lauryn Hill sets Grammy record - February 24, 1999". www.cnn.com. Retrieved 2022-06-15.
  10. ^ "1999 GRAMMY AWARDS // Lauryn Hill wins Album of the Year; Madonna, "Titanic' get 3 Grammys". Tampa Bay Times. Retrieved 2022-06-15.
  11. ^ "1998 Grammy Award Winners". Grammy.com. Retrieved 1 May 2011.
  12. ^ "Ricky Martin Comes Full Circle at the Grammys, 20 Years After His Historic Breakthrough Performance: 'We Are Here to Stay'". Billboard. 2019-02-07. Retrieved 2022-06-15.