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 performed Express Yourself at the 6th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA. The Express Yourself music video picked up awards for Best Direction, Best Art Direction, Best Cinematography, while Like A Prayer won the Viewer’s Choice Award.
Serving as a sneak preview for 1990’s Blond Ambition Tour, the performance marked the first of many to feature the vocal trio of Madonna, Donna De Lory and Niki Haris. De Lory and Haris had previously toured with Madonna during the 1987 Who’s That Girl Tour, but had been joined by a third background vocalist, Debra Parsons. The pair would be more heavily featured as vocalist/dancers from this point forward, rather than simply band members who rarely left the confines of their microphone stand.
It was during rehearsals for the 1989 VMA performance that Niki Haris brought voguing to Madonna’s attention, and stylized poses were then fittingly incorporated into the performance’s choreography. While the performance is relatively simple compared to her numerous VMA performances in the years that followed, this puts the focus on the trio’s excellent live vocals and kick-ass choreography (keeping in mind that vocally, Express Yourself is quite a workout even without the dancing!). I consider this a great example of how sometimes less is more, and I would definitely consider this among her best awards show performances.
On September 2 1993, Madonna opened the 1993 MTV Video Music Awards performing Bye Bye Baby. She cavorted on stage with three scantily clad women in a brothel-style setting, dressed in tuxedos and top hats, in a choreographed, highly sexual routine. According to choreographer Alex Magno, he wanted to do Justify My Love or The Beast Within on MTV, but Madonna decided that they might be too controversial for live television and abandoned the idea. Nevertheless, Bye Bye Baby was chosen and performed with the choreography they had been practicing for The Girlie Show World Tour, since it represented the whole idea behind the tour. Louis Virtel from The Backlot ranked the performance at number eight on a list for Madonna’s 11 Greatest VMA Moments. He praised Madonna’s rendition of the song at the Video Music Awards, calling it “a hell of a VMA performance” and a “killer cinematic throwback”.
On September 14 1984, Madonna performed Like A Virgin and was nominated for Best New Artist Video (Borderline) at the 1st annual MTV Video Music Awards at Radio City Music Hall, New York, NY.
Madonna recalled the infamous performance in a 2012 interview on The Tonight Show with Jay Leno: “I was standing at the top of a wedding cake, as one does, and I walked down these steps, which were the tiers of a wedding cake. And I lost my shoe. I lost my white stiletto. And I thought, ‘Oh god, how am I going to get that? It’s over there and I’m on TV.’ So I thought well, I’ll just pretend I meant to do this and I dove on to the floor and I rolled around and I reached for the shoe. And, as I reached for the shoe, the dress went up. And the underpants were showing and uhm, I didn’t mean to…” To which Leno chided: “And it became the greatest night in television history.”
We’re not too sure about Madonna’s recollection of the performance. Looks like the shoes came off quite intentionally to us. Check out the video and let us know what you think!
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!