The 1999 MTV Video Music Awards, which took place on September 9, 1999 (informally known as the 9/9/99 MTV Video Music Awards), honored the best music videos released between June 13, 1998, and June 11, 1999. The ceremony was hosted by Chris Rock and held at the Metropolitan Opera House in New York City. Lauryn Hill was the biggest winner of the night, earning four awards, including the prestigious Video of the Year for "Doo Wop (That Thing)", making it the first hip-hop video to win in that category. Ricky Martin won two competitive awards for "Livin’ la Vida Loca": Best Pop Video and Best Dance Video. In addition, he received three International Viewer's Choice Awards, which were presented at the ceremony. Other notable winners included Korn, TLC, and Eminem.

Highlights of the show included Diana Ross jiggling Lil' Kim's exposed breast in response to her outfit, which left her entire left breast uncovered, but for a small pastie on her nipple. The mothers of slain rappers Tupac Shakur and The Notorious B.I.G., Afeni Shakur and Voletta Wallace, came together to present the Best Rap Video Award. The Beastie Boys' Adam Horovitz made a plea for peace in the wake of the sexual assaults at Woodstock '99. Near the end of the night, MTV staged a tribute to Madonna, the most-nominated artist in VMA history, by presenting a host of male drag performers dressed as the singer in her past music videos. Rapper DMX was scheduled to perform but was a no-show; as a result, Jay-Z's solo set was extended. Another moment of the ceremony was the debut of Britney Spears performing her debut single "...Baby One More Time", and then, NSYNC, performed their song "Tearin' Up My Heart".

As Backstreet Boys came up and accepted their award for Viewer's Choice, a stranger came onto the stage and said, "Wake up at 3". This person was later revealed to be John Del Signore, who crashed the ceremony in a failed attempt to sell Viacom a show idea.

The awards show featured a line-up of sponsors and cross-promotions, most notably with SEGA, as the date of the show also coincided with the launch of their Dreamcast game console.

After scouting locations in both New York and Los Angeles, MTV announced in May that the 1999 MTV Video Music Awards would be held at New York's Metropolitan Opera House at Lincoln Center. (MTV's traditional New York venue, Radio City Music Hall, was closed for renovations at the time.) Comedian Chris Rock was announced as the ceremony's host on June 30. Nominations were announced at a press conference hosted by Rock, Carson Daly, and Ricky Martin and held at Lincoln Center on July 28. For the first time, the ceremony was promoted with a "VMA Week" on Total Request Live, which would continue annually until that program's cancellation in 2008. The ceremony broadcast was preceded by the 1999 MTV Video Music Awards Opening Act. Hosted by Kurt Loder and Serena Altschul with reports from Chris Connelly, Carson Daly, Ananda Lewis, and John Norris, the broadcast featured red carpet interviews, a pre-taped interview with Trent Reznor, pre-taped features on Britney Spears' outfit selection and testing various singers' vocal ability to shatter glass, and performances from Smash Mouth and Blink-182.

Winners are listed first and highlighted in bold.