The 1999 Billboard Music Awards took place on December 8, 1999, at the MGM Grand Garden Arena in Las Vegas. Hosted by Kathy Griffin and Adam Carolla, the ceremony honored the best-performing music releases between December 1998 and November 1999, and their respective artists.
Britney Spears was both the most-nominated and most-awarded artist of the year, winning five awards including Top New Artist and Top Female Artist. Country singer and songwriter Emmylou Harris was bestowed with the Century Award in honour of her many creative achievements, while Aerosmith received the Artist Achievement Award for their longstanding body of work. Garth Brooks and Mariah Carey were recipients of the inaugural Male and Female Artist of the Decade awards respectively. The Red Hot Chili Peppers were presented with a special award for their single "Scar Tissue", which set the then-all-time record for most weeks at number-one on Billboards Hot Modern Rock Tracks chart earlier in the year.
Performances Artist(s) Song(s) Jennifer Lopez "Waiting for Tonight" Red Hot Chili Peppers "Scar Tissue""Red Hot Mama" Britney Spears "...Baby One More Time""(You Drive Me) Crazy" LeAnn Rimes "Crazy" Metallica "Until It Sleeps" Juvenile "Back That Thang Up" Ricky Martin "Shake Your Bon-Bon" Mariah Carey "I Still Believe" Celine Dion "That's The Way It Is"
Presenters Jessica Simpson & Sugar Ray – presented Top Billboard 200 Album Jennifer Love Hewitt & Diego Serrano – introduced Britney Spears Lou Bega, Mae Young & The Fabulous Moolah – presented Top Rap Artist Brian McKnight & Vitamin C – presented Top Country Artist of the Year Ben Affleck – presented the Artist Achievement Award to Aerosmith Mary J Blige & Everlast – presented Top R&B/Hip Hop Artist Christina Aguilera & 98 Degrees – presented Top Male Artist Dennis Hopper – introduced LeAnn Rimes Mila Kunis & Laura Prepon – introduced *NSYNC *NSYNC – presented Top Female Artist Mandy Moore & Darren Hayes – announced the winners in the Rock/Modern Rock categories Oscar De La Hoya – introduced Ricky Martin Patti LaBelle – presented Female Artist of the Decade to Mariah Carey Sarah McLachlan – presented the Century Award to Emmylou Harris James Hetfield & Lars Ulrich – presented Artist of the Year
Winners and nominees Britney Spears was the most-nominated artist with eight nominations, followed by TLC who received six. R. Kelly and Cher tied with five nominations apiece, while Whitney Houston, Shania Twain, Jay-Z, and the Backstreet Boys each earned four.
Winners are listed first and highlighted in bold. Artist of the Year Top New Artist Backstreet Boys Britney Spears TLC Shania Twain Britney Spears Christina Aguilera Lou Bega Jennifer Lopez Top Male Artist Top Female Artist Ricky Martin Jay-Z R. Kelly DMX Britney Spears Cher Whitney Houston Shania Twain Top Billboard 200 Artist Top Billboard 200 Album Backstreet Boys Britney Spears TLC Shania Twain Backstreet Boys – Millennium *NSYNC – *NSYNC Britney Spears – ...Baby One More Time Shania Twain – Come On Over Female Singles Artist of the Year Top Female Albums Artist of the Year "...Baby One More Time" – Britney Spears Britney Spears – ...Baby One More Time Top Duo/Group Top Hot 100 Song Backstreet Boys 98 Degrees Sugar Ray TLC "Believe" – Cher "Heartbreak Hotel" – Whitney Houston (featuring Faith Evans and Kelly Price) "Angel of Mine" – Monica "No Scrubs" – TLC Top Male Hot 100 Artist of the Year Top Female Hot 100 Artist of the Year Ricky Martin R. Kelly Jay-Z Tim McGraw Britney Spears Cher Whitney Houston Brandy Norwood Top R&B/Hip Hop Artist Top R&B Album Artist of the Year R. Kelly Faith Evans Lauryn Hill Jay-Z Flesh of My Flesh, Blood of My Blood – DMX 400 Degreez – Juvenile The Miseducation of Lauryn Hill – Lauryn Hill R. – R. Kelly Top R&B Album of the Year Top R&B Single of the Year ''400 Degreez – Juvenile Flesh of My Flesh, Blood of My Blood – DMX The Miseducation of Lauryn Hill – Lauryn Hill R. – R. Kelly | valign="top" | "Fortunate" – Maxwell "Nobody's Supposed to Be Here" – Deborah Cox "Heartbreak Hotel" – Whitney Houston (featuring Faith Evans and Kelly Price) "No Scrubs" – TLC |- ! style="background:#EEDD82; width:50%" | Top Rap Artist ! style="background:#EEDD82; width:50%" | Top Rap Single |- | valign="top" | Jay-Z Busta Rhymes JT Money Solé | valign="top" | "Who Dat" – JT Money featuring Solé "What's It Gonna Be?!" – Busta Rhymes (featuring Janet Jackson) "Ghetto Cowboy" – Mo Thugs (featuring Bone Thugs-N-Harmony) "Somebody Like Me – Silkk the Shocker |- ! style="background:#EEDD82; width:50%" | Top Country Artist of the Year ! style="background:#EEDD82; width:50%" | Top Country Album of the Year |- | valign="top" | Dixie Chicks Martina McBride Tim McGraw George Strait | valign="top" | Wide Open Spaces – Dixie Chicks|- ! style="background:#EEDD82; width:50%" | Top Country Group/Duo of the Year ! style="background:#EEDD82; width:50%" | Adult Contemporary Track Of The Year |- | valign="top" | Dixie Chicks| valign="top" | "Angel" – Sarah McLachlan|- ! style="background:#EEDD82; width:50%" | Top Rock Artist of the Year ! style="background:#EEDD82; width:50%" | Top Rock Single of the Year |- | valign="top" | Creed Collective Soul Lenny Kravitz Metallica | valign="top" | "One" – Creed "Heavy" – Collective Soul "What It's Like" – Everlast "Scar Tissue" – Red Hot Chili Peppers |- ! style="background:#EEDD82; width:50%" | Top Modern Rock Artist ! style="background:#EEDD82; width:50%" | Top Modern Rock Track |- | valign="top" | The Offspring | valign="top" | "My Own Worst Enemy" – Lit|- ! style="background:#EEDD82; width:50%" | Top Catalog Artist of the Year ! style="background:#EEDD82; width:50%" | Top Catalog Album of the Year |- | valign="top" | Metallica | valign="top" | Metallica'' – Metallica Century Award Artist Achievement Award Emmylou Harris Aerosmith Male Artist of the Decade Female Artist of the Decade Garth Brooks Mariah Carey
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