The idea for the 'Madonna Through the Years' tribute was taken from a Los Angeles stage show already several years in production titled The Blonde Exhibition. Producer Dan Gore started the theatre show in the early 1990s, hiring several look and sound-alike Madonna performers to re-create the artist's performance career on stage. His last show was a year before the MTV Video Music Awards broadcast at the El Rey Theatre in Los Angeles.
The MTV Video Music Award for Best Artist Website was given out once in 1999 during the Pre-Show, and was then discontinued. The winners were the Red Hot Chili Peppers for their official website, run by Webmaster Jon Wade, News Director Starla Angel, Head Honcho Blackie Dammet (father of Anthony Kiedis) and Web Designer Terry Wells.
Originally, the producers of the show tried to coax the former boy band New Kids On The Block to perform at the ceremony and present an award.