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.
On September 6 1989, Madonna presented the Video Vanguard Award to George Michael at the 6th annual MTV Video Music Awards at the Universal Amphitheatre in Los Angeles, California. Madonna also performed her hit Express Yourself during the show.
On September 5 1986, Madonna was honoured with the Video Vanguard Award for her visionary videos at the 3rd annual MTV Video Music Awards at the Palladium in New York City.
Madonna found immense popularity by pushing the boundaries of lyrical content in mainstream popular music and imagery in her music videos, which became a fixture on MTV. Her videos depicted controversial subjects such as teen pregnancy, racism, religion, sex and violence. She received the Video Vanguard Award for her contributions to the world of music video.
On September 11 1987, Madonna won Best Female Video for Papa Don’t Preach at the MTV Video Music Awards at the Universal Amphitheatre in Los Angeles.
Having just completed her Who’s That Girl World Tour in Europe, Madonna did not attend the ceremony in person. Instead, a performance of Causing A Commotion recorded the week before in Turin, Italy was featured during the broadcast.
On September 7 1995, Madonna won Best Female Video for “Take A Bow” at the 12th annual MTV Video Music Awards at Radio City Music Hall, New York, NY. Madonna also presented the award for Best Rap Video.
Later, a post-show chat with Kurt Loder to promote her upcoming ballads collection Something To Remember quickly went off the rails when Courtney Love infamously interrupted the interview. While it may have been Liz Rosenberg’s worst nightmare, the hilarious encounter certainly gave viewers something to remember!