Gli MTV Video Music Awards 1999 sono stati la 16ª edizione dell'omonimo premio e si sono svolti il 9 settembre 1999 al Metropolitan Opera House di New York. In quest'edizione sono stati premiati i migliori video pubblicati tra il 13 giugno 1998 e l'11 giugno 1999.

Quest'edizione è stata presentata da Chris Rock e Lauryn Hill ha vinto in quattro categorie, risultando la più premiata della serata.^[1]

• Kid Rock (feat. Run-DMC, Steven Tyler, Joe Perry & Joe C.)
• Lauryn Hill
• Backstreet Boys
• Ricky Martin
• Nine Inch Nails
• TLC
• Fatboy Slim
• Jay-Z (feat. DJ Clue & Amil)
• Britney Spears & 'N Sync
• Eminem & Dr. Dre & Snoop Dogg

I vincitori^[2] sono scritti in grassetto.

• Lauryn Hill - Doo Wop (That Thing)
• Backstreet Boys - I Want It That Way
• Korn - Freak on a Leash
• Ricky Martin - Livin' la vida loca
• Will Smith feat. Dru Hill & Kool Moe Dee - Wild Wild West

• Will Smith - Miami
• Eminem - My Name Is
• Lenny Kravitz - Fly Away
• Ricky Martin - Livin' la vida loca

• Lauryn Hill - Doo Wop (That Thing)
• Jennifer Lopez - If You Had My Love
• Madonna - Beautiful Stranger
• Britney Spears - ...Baby One More Time

• TLC - No Scrubs
• Backstreet Boys - I Want It That Way
• Limp Bizkit - Nookie
• NSYNC - Tearin' Up My Heart
• Sugar Ray - Every Morning

• Ricky Martin - Livin' la vida loca
• Backstreet Boys - I Want It That Way
• Jennifer Lopez - If You Had My Love
• NSYNC - Tearin' Up My Heart
• Britney Spears - ...Baby One More Time

• Jay Z feat. Ja Rule & Amil - Can I Get a...
• Tupac Shakur- Changes
• DMX - Ruff Ryder's Anthem (Stop Drop)
• Nelly feat. Puff Diddy - Hate Me Now

• Lauryn Hill - Doo Wop (That Thing)
• Aaliyah - Are You That Somebody?
• Brandy- Have You Ever?
• Whitney Houston feat. Faith Evans & Kelly Price - Heartbreak Hotel

• Beastie Boys - Intergalactic
• Busta Rhymes feat. Janet Jackson - What's It Gonna Be ?!
• Lauryn Hill - Doo Wop (That Thing)
• TLC- No Scrubs

• Ricky Martin - Livin' la vida loca
• Cher - Believe
• Fatboy Slim - Praise You
• Jordan Knight - Give It to You
• Jennifer Lopez - If You Had My Love

• Korn - Freak on a Leash
• Limp Bizkit - Nookie
• Kid Rock - Bawitdaba
• Lenny Kravitz - Fly Away
• The Offspring - Pretty Fly (for a White Guy)

• Eminem - My Name Is
• Kid Rock - Bawitdaba
• Jennifer Lopez - If You Had My Name
• Orgy - Blue Monday

• Madonna - Beautiful Stranger
• Aaliyah - Are You That Somebody?
• Jay Z feat. Ja Rule & Amil - Can I Get a...
• Will Smith feat. Dru Hill & Kool Moe Dee - Wild Wild West

• Fatboy Slim - Praise You
• Busta Rhymes feat. Janet Jackson - What's It Gonna Be
• Eminem - My Name Is
• Korn - Freak on a Leash
• TLC - No Scrubs

• Fatboy Slim - Praise You
• Ricky Martin - Livin' la vida loca
• Will Smith feat. Dru Hill & Kool Moe Dee - Wild Wild West
• Britney Spears - ...Baby One More Time

• Garbage - Special
• The Black Eyed Peas - Joints & Jams
• Busta Rhymes feat. Janet Jackson - What's It Gonna Be
• Korn - Freak on a Leash
• Madonna - Nothing Really Matters
• Will Smith - Miami

• Lauryn Hill - Doo Wop (That Thing)
• Barenaked Ladies - One Week
• Busta Rhymes feat. Janet Jackson - What's It Gonna Be
• Korn - Freak on a Leash
• TLC - No Scrubs

• Korn - Freak on a Leash
• Tupac Shakur - Changes
• Cher - Believe
• TLC - No Scrubs

• Marilyn Manson - The Dope Show
• Hole - Malibù
• Korn - Freak on a Leash
• Madonna - Beautiful Stranger
• Will Smith - Miami

• Fatboy Slim - Praise You
• Busta Rhymes - Gimme Some More
• Eels - Last Stop: This Town
• Eminem feat. Dr. Dre - Guilty Coscience
• Korn - Freak on a Leash
• U.N.K.L.E. - Rabbit In Your Headlight

• Backstreet Boys - I Want It That Way
• NSYNC - Tearin' Up My Heart
• Jay Z feat. Ja Rule & Amil - Can I Get a...
• Korn - Freak on a Leash
• Ricky Martin - Livin' la vida loca
• TLC - No Scrubs

• Sito ufficiale, su mtv.com.

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