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27th Annual American Music Awards The winners of the 27th Annual American Music Awards were announced January 17, 2000. | POP/ROCK | | Favorite Male Artist | Will Smith | | Favorite Female Artist | Shania Twain | | Favorite Band, Duo or Group | Backstreet Boys | | Favorite Album | Supernatural, Santana | | Favorite New Artist | Britney Spears |
| | SOUL/RHYTHM & BLUES | | Favorite Male Artist | R. Kelly | | Favorite Female Artist | Lauryn Hill | | Favorite Band, Duo or Group | TLC | | Favorite Album | The Miseducation of Lauryn Hill, Lauryn Hill | | Favorite New Artist | Tyrese |
| | COUNTRY | | Favorite Male Artist | Garth Brooks | | Favorite Female Artist | Shania Twain | | Favorite Band, Duo or Group | Brooks and Dunn | | Favorite Album | Double Live, Garth Brooks | | Favorite New Artist | Montgomery Gentry |
| | ADULT CONTEMPORARY | | Favorite Artist | Phil Collins |
| | RAP/HIP-HOP | | | LATIN MUSIC | | Favorite Artist | Ricky Martin |
| | SOUNDTRACK | | Favorite Artist | Wild Wild West |
| | ALTERNATIVE MUSIC | | Favorite Artist | Red Hot Chili Peppers |
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