On September 10 1998, Madonna performed Shanti/Ashtangi and Ray Of Light at the 15th annual MTV Video Music Awards at the Universal Amphitheatre in Los Angeles, California. Ray Of Light won Best Video, Best Female Video, Best Direction (Jonas Åkerlund), Best Choreography, Best Editing and Frozen won Best Special Effects.
On September 4 1987, Madonna performed Causing A Commotion live via satellite from the Stadio Communale in Turin, Italy, during the Who’s That Girl World Tour and won Best Female Video for Papa Don’t Preach at the 4th annual MTV Video Music Awards at the Universal Amphitheatre in Los Angeles, California.
On August 28 2003, Madonna performed Hollywood with Britney Spears and Christina Aguilera as the opening number for the 20th annual MTV Video Music Awards at Radio City Music Hall, New York, NY and upstaged everyone at the ceremony when she shares a passionate open-mouth kiss with them. Missy Elliott also joined the ladies on stage – post-kiss.
Madonna commented on the uproar surrounding the infamous kiss during an appearance on Oprah several weeks later. “I don’t know why people are making such a big deal about it,” she said. “Hasn’t anyone seen two girls kiss before? It was a friendly kiss – it really was. If Britney looks as though she is kissing me in an aggressive way it was a surprise to me.” She added, “I’m a showgirl. After 20 years in the business, we learn to roll with the punches. If someone’s coming at you with lips slightly parted, you kiss them.”
On September 9 1999, MTV staged a tribute to Madonna, the most-nominated artist in Video Music Award history, by presenting a host of male drag performers dressed up as Madonna from her past music videos.
Madonna also introduced Paul McCartney, and then together they presented the Video of the Year.
Madonna was also nominated and won a VMA for:
- Best Video from a Film – Beautiful Stranger
Beautiful Stranger was also nominated for:
- Best Female Video
- Best Cinematography
- Best Visual Effects
On September 8 1994, Madonna presented the award for Video of the Year at the MTV VMA’s. She was escorted onstage by David Letterman, poking fun at their supposed feud following Madonna’s infamous profanity propelled appearance on Letterman earlier that year.
The appearance was intended to generate buzz for her soon-to-be-released single, Secret and its accompanying album, Bedtime Stories.