1999 MTV Video Music Awards

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.

This person was later revealed to be John Del Signore, who crashed the ceremony in a failed attempt to sell Viacom a show idea.

[8] Nominations were announced at a press conference hosted by Rock, Carson Daly, and Ricky Martin and held at Lincoln Center on July 28.

[9] 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.

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.