1999 MTV Video Music Awards

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 (featuring Dru Hill and 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"

Eminem – "My Name Is"

• Kid Rock – "Bawitdaba"
• Jennifer Lopez – "If You Had My Love"
• Orgy – "Blue Monday"

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"

Korn – "Freak on a Leash"

• Kid Rock – "Bawitdaba"
• Lenny Kravitz – "Fly Away"
• Limp Bizkit – "Nookie"
• The Offspring – "Pretty Fly (for a White Guy)"

Lauryn Hill – "Doo Wop (That Thing)"

• Aaliyah – "Are You That Somebody?"
• Brandy – "Have You Ever?"
• Whitney Houston (featuring Faith Evans and Kelly Price) – "Heartbreak Hotel"

Jay-Z (featuring Ja Rule and Amil) – "Can I Get A..."

• 2Pac – "Changes"
• DMX – "Ruff Ryders' Anthem"
• Nas (featuring Puff Daddy) – "Hate Me Now"

Beastie Boys – "Intergalactic"

• Busta Rhymes (featuring 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"

Madonna – "Beautiful Stranger" (from Austin Powers: The Spy Who Shagged Me)

• Aaliyah – "Are You That Somebody?" (from Dr. Dolittle)
• Jay-Z (featuring Ja Rule and Amil) – "Can I Get A..." (from Rush Hour)
• Will Smith (featuring Dru Hill and Kool Moe Dee) – "Wild Wild West" (from Wild Wild West)

Fatboy Slim – "Praise You"

• Busta Rhymes – "Gimme Some More"
• Eels – "Last Stop: This Town"
• Eminem (featuring Dr. Dre) – "Guilty Conscience"
• Korn – "Freak on a Leash"
• Unkle (featuring Thom Yorke) – "Rabbit in Your Headlights"

Fatboy Slim – "Praise You" (Director: Torrance Community Dance Group)

• Busta Rhymes (featuring Janet Jackson) – "What's It Gonna Be?!" (Directors: Hype Williams and Busta Rhymes)
• Eminem – "My Name Is" (Directors: Dr. Dre and Phillip Atwell)
• Korn – "Freak on a Leash" (Directors: Todd McFarlane, Graham Morris, Jonathan Dayton and Valerie Faris)
• TLC – "No Scrubs" (Director: Hype Williams)

Fatboy Slim – "Praise You" (Choreographers: Richard Koufey and Michael Rooney)

• Ricky Martin – "Livin' la Vida Loca" (Choreographer: Tina Landon)
• Will Smith (featuring Dru Hill and Kool Moe Dee) – "Wild Wild West" (Choreographer: Fatima Robinson)
• Britney Spears – "...Baby One More Time" (Choreographer: Randy Connor)

Garbage – "Special" (Special Effects: Sean Broughton, Stuart D. Gordon and Paul Simpson of Digital Domain)

• The Black Eyed Peas – "Joints & Jam" (Special Effects: Brian Beletic and Todd Somodivilla)
• Busta Rhymes (featuring Janet Jackson) – "What's It Gonna Be?!" (Special Effects: Fred Raimondi)
• Korn – "Freak on a Leash" (Special Effects: Matt Beck, Edson Williams, and the Brothers Strause)
• Madonna – "Nothing Really Matters" (Special Effects: Johan Renck, Bjorn Benckert and Tor-Bjorn Olsson)
• Will Smith – "Miami" (Special Effects: Eric Swenson, Andrea Mansour and Simon Mowbray)

Lauryn Hill – "Doo Wop (That Thing)" (Art Director: Gideon Ponte)

• Barenaked Ladies – "One Week" (Art Director: Paul Martin)
• Busta Rhymes (featuring Janet Jackson) – "What's It Gonna Be?!" (Art Director: Regan Jackson)
• Korn – "Freak on a Leash" (Art Directors: K. K. Barrett, Todd McFarlane, Terry Fitzgerald and Graham Morris)
• TLC – "No Scrubs" (Art Director: Regan Jackson)

Korn – "Freak on a Leash" (Editors: Haines Hall and Michael Sachs)

• 2Pac – "Changes" (Editor: Chris Hafner)
• Cher – "Believe" (Editor: Scott Richter)
• TLC – "No Scrubs" (Editor: Harvey White)

Marilyn Manson – "The Dope Show" (Director of Photography: Martin Coppen)

• Hole – "Malibu" (Director of Photography: Martin Coppen)
• Korn – "Freak on a Leash" (Director of Photography: Julian Whatley)
• Madonna – "Beautiful Stranger" (Director of Photography: Thomas Kloss)
• Will Smith – "Miami" (Director of Photography: Daniel Pearl)

Red Hot Chili Peppers (www.redhotchilipeppers.com)

• David Bowie (www.davidbowie.com)
• Sheryl Crow (www.sherylcrow.com)
• Jennifer Lopez (www.jenniferlopez.com)
• Limp Bizkit (www.limp-bizkit.com)
• Massive Attack (www.massiveattack.co.uk)
• The Smashing Pumpkins (www.smashingpumpkins.com)

Backstreet Boys – "I Want It That Way"

• Jay-Z (featuring Ja Rule and Amil) – "Can I Get A..."
• Korn – "Freak on a Leash"
• Ricky Martin – "Livin' la Vida Loca"
• NSYNC – "Tearin' Up My Heart"
• TLC – "No Scrubs"

Silverchair – "Anthem for the Year 2000"

• Neil Finn – "Sinner"
• The Living End – "Save the Day"
• Powderfinger – "Already Gone"
• Spiderbait – "Stevie"

Raimundos – "Mulher de Fases"

• Banda Eva – "De Ladinho"
• Barão Vermelho – "Por Você"
• Capital Inicial – "O Mundo"
• Charlie Brown Jr. – "Zoio D Lula"
• Cidade Negra – "Já Foi"
• Claudinho e Buchecha – "Só Love"
• Engenheiros do Hawaii – "Eu Que Não Amo Você"
• Jota Quest – "Sempre Assim"
• Kid Abelha – "Eu Só Penso em Você"
• Leonardo – "120, 150, 200 km/h"
• Nativus – "Liberdade pra Dentro da Cabeça"
• Os Paralamas do Sucesso – "Depois da Queda o Coice"
• Pato Fu – "Canção pra Você Viver Mais"
• Pepê e Neném – "Mania de Você"
• Sandy & Junior – "No Fundo do Coração"
• SPC – "Sai da Minha Aba (Bicão)"
• Skank – "Mandrake e os Cubanos"
• Caetano Veloso – "Sozinho"
• Vinny – "Shake Boom"[3]

A. R. Rahman – "Dil Se Re"

• Shankar Mahadevan – "Breathless"
• Sonu Nigam – "Ab Mujhe Raat Din"
• Alka Yagnik and Udit Narayan – "Kuch Kuch Hota Hain"
• Alka Yagnik and Udit Narayan – "Mera Mann"

H.O.T. – "Make a Line"

• Cho Sung Mo – "To Heaven"
• Jinusean – "Taekwon V"
• No Brain – "Youth 98"
• Shin Hae Chul – "Invitation to My Daily Life"
• Yoo Seung Jun – "Burning Love"

Ricky Martin – "Livin' la Vida Loca"

• Bersuit Vergarabat – "Sr. Cobranza"
• Café Tacuba – "Revés"
• Control Machete – "Sí, Señor"
• Molotov – "El Carnal de las Estrellas"

Ricky Martin – "Livin' la Vida Loca"

• Los Auténticos Decadentes – "Los Piratas"
• Miguel Mateos – "Bar Imperio"
• Molotov – "El Carnal de las Estrellas"
• Los Pericos – "Sin Cadenas"

Shino Lin – "Irritated"

• Chau Wa-Kin – "Someone with a Story"
• Valen Hsu – "Don't Say Goodbye"
• Faye Wong – "Quitting in Halfway"
• Harlem Yu and Jeff Chang – "Love Turning Around"
• Zhang Chen-Yu – "I Want Money"
• Zheng Jun – "Happiness"

Ricky Martin – "Livin' la Vida Loca"

• Linda – "Otpusti Menyia"
• Mumiy Troll – "Ranetka"
• The Offspring – "Pretty Fly (for a White Guy)"
• Otpetye Moshenniki – "Lyubi Menia, Lyubi"
• Britney Spears – "...Baby One More Time"

Parokya ni Edgar – "Harana"

• Mai Charoenpura – "Mai Han Pen Rai"
• Krisdayanti – "Menghitung Hari"
• Poetic Ammo – "Everything Changes"

• Smash Mouth – "All Star"
• Blink-182 – "What's My Age Again?"/"All the Small Things"[4]

• Kid Rock (featuring Run-DMC, Steven Tyler, Joe Perry and Joe C.) – "King of Rock" / "Rock Box" / "Bawitdaba" / "Walk This Way"
• Lauryn Hill – "Lost Ones" / "Everything Is Everything"
• Backstreet Boys – "I Want It That Way" / "Larger Than Life"
• Ricky Martin – "She's All I Ever Had" / "Livin' la Vida Loca"
• Nine Inch Nails – "The Fragile"
• TLC – "No Scrubs"
• Fatboy Slim – "Praise You"
• Jay-Z (featuring DJ Clue and Amil) – "Jigga My Nigga" / "Can I Get A..." / "Hard Knock Life (Ghetto Anthem)"
• Britney Spears and NSYNC – "...Baby One More Time" / "Tearin' Up My Heart"
• Eminem, Dr. Dre and Snoop Dogg – "My Name Is" / "Guilty Conscience" / "Nuthin' But a "G" Thang"

• Chris Connelly and Ananda Lewis – announced the winners of the professional categories and presented Best R&B Video.[5]

• Moby – DJed during the commercial breaks
• Wyclef Jean and Charlotte Church – presented Best New Artist in a Video
• Chris Rock – introduced Britney Spears and NSYNC
• Johnny Depp – introduced Nine Inch Nails
• Renée Zellweger and Jay Mohr – introduced the International Viewer's Choice Awards winners
• David Bowie – introduced Lauryn Hill
• Regis Philbin – introduced Fatboy Slim, Richard Koufey and the Torrance Community Dance Group
• Prince – introduced TLC
• Christina Aguilera and Tommy Lee – presented Best Rock Video
• Stone Cold Steve Austin – introduced Jay-Z
• Mark McGrath and Jennifer Lopez – presented Best Video From a Film
• Chris Rock – introduced Ricky Martin
• Gavin Rossdale and Susan Sarandon – presented Best Female Video
• Mira Sorvino and Freddie Prinze Jr. – presented Best Male Video
• Limp Bizkit (Fred Durst and Wes Borland) and Heather Locklear – presented Best Pop Video
• Tom Green – appeared in vignettes about Viewer's Choice voting procedures
• Will Smith – introduced Afeni Shakur and Voletta Wallace and presented Best Rap Video with them
• Mary J. Blige and Lil' Kim – introduced Diana Ross and presented Best Hip-Hop Video with her
• Carson Daly and Pamela Anderson – described balloting procedures, and introduced the Backstreet Boys
• Janet Jackson – presented Best Dance Video
• Janeane Garofalo and Method Man – presented Breakthrough Video
• Puff Daddy and Denise Richards – presented Best Group Video
• Buddy Hackett, Heather Donahue, Joshua Leonard and Michael C. Williams – presented Best Direction in a Video
• Chris Rock – introduced Kid Rock
• Rebecca Romijn-Stamos, Heidi Klum and Tim Robbins – presented Viewer's Choice
• Lars Ulrich – introduced Eminem
• Madonna – introduced Paul McCartney and presented Video of the Year with him