In the history of the MTV Video Music Awards, no artist has taken home more Moonmen than Madonna. The Material Girl, who performed at the very first VMAs in 1984 and most recently introduced the Michael Jackson tribute at last year's show, has taken home a grand total of 20 Video Music Awards across her illustrious career, and on this day in 1998, she scored six prizes in one night, including her only win for Video of the Year (for "Ray of Light," which won five; she got one more for "Frozen").
It was fitting that Madonna had such a huge night at the 1998 MTV Video Music Awards. She had been away from pop music for a few years (she had instead been focusing on films, including the title role in the movie musical "Evita"). The last time she made an impact on the music scene was with the strange, esoteric Bedtime Stories album, and nobody really knew what a new Madonna album would sound like. But with the word "electronica" on the lips of pundits and popologists, it's no wonder that Madonna chose to craft an album full of up-to-the-minute electronic music and neck-snapping dance tracks. It was yet another reinvention for her, and it was nothing short of brilliant.
Madonna had a great night at the 1998 Video Music Awards. In addition to winning the six awards (Video of the Year, Best Female Video, Best Direction, Best Choreography, Best Editing and Best Special Effects), she also opened up the show with a rousing one-two punch of "Shanti" and "Ray of Light" (the latter of which featured a guest spot by Lenny Kravitz on guitar). Even 12 years later, "Ray of Light" (which beat out Will Smith's "Gettin' Jiggy Wit It," the Verve's "Bitter Sweet Symphony," Diddy's "It's All About the Benjamins" and Brandy and Monica's "The Boy is Mine" for the Video of the Year victory) still holds up as an incredible accomplishment.