Today in Madonna History: September 2, 1993

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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”.

Today in Madonna History: August 28, 2003

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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.”

Today in Madonna History: August 18, 2026

On August 18, 2026, nominations for the 2026 MTV Video Music Awards were announced, with Madonna leading all artists with an incredible 11 nominations — the most VMA nominations she has ever received in a single year.

The nominations recognize both Confessions II – The Film and Bring Your Love with Sabrina Carpenter, with Madonna competing in some of the night’s biggest categories, including Video of the Year, Artist of the Year and Song of the Year.

Madonna’s 11 nominations are:

• Video of the Year — Confessions II – The Film
• Artist of the Year
• Song of the Year — “Bring Your Love” with Sabrina Carpenter
• Best Collaboration — “Bring Your Love” with Sabrina Carpenter
• Best Dance — Confessions II – The Film
• Best Direction — Confessions II – The Film
• Best Art Direction — Confessions II – The Film
• Best Cinematography — Confessions II – The Film
• Best Editing — Confessions II – The Film
• Best Choreography — Confessions II – The Film
• Best Visual Effects — Confessions II – The Film

The nominations add another chapter to Madonna’s extraordinary history with MTV. Forty-two years after her legendary “Like a Virgin” performance at the inaugural VMAs in 1984, Madonna is once again the most-nominated artist of the year. She has now received VMA nominations in every decade of her career.

The 2026 MTV Video Music Awards will air live from the Peacock Theater in Los Angeles on Sunday, September 27, on CBS and MTV, with streaming on Paramount+.

Not bad for a relationship that started with a wedding dress, a giant cake and a Boy Toy belt. ❤️🏆

And because one Madonna celebration is never enough, we’re adding a few bonus photos from her recent 68th birthday. ❤️👑

Today in Madonna History: May 12, 1998

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On May 12 1998, Madonna’s Ray of Light video premiered on MTV.

The video was directed by Jonas Åkerlund, with Madonna’s scenes being shot on March 25–26, 1998 at Raleigh Studios and Florentine Gardens nightclub in downtown Los Angeles. The images of various cities include Los Angeles, New York, London, Las Vegas and Stockholm.

The video was ranked No. 40 on VH1’s 100 Greatest Videos, listed No. 1 on Back In… 98’s Top 5 Best Videos, ranked No. 7 on Listed’s Top 40 Memorable Videos Pt. 1 & 2, on MuchMoreMusic, and ranked No. 26 on MuchMusic’s 100 Best Videos. It was ranked at number four on “The Top 100 Videos That Broke The Rules”, issued by MTV on the channel’s 25th anniversary in August 2006.

The video received a total of eight MTV Video Music Awards nominations, becoming Madonna’s second most-nominated video at the award show, after “Vogue” in 1990. It won five awards for Video of the Year, Best Female Video, Best Direction, Best Editing and Best Choreography, becoming her most-winning song at the show.

Today in Madonna History: September 7, 1995

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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!

Today in Madonna History: September 5, 1986

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.

While there’s no denying Madonna was an early innovator in the art of music video, little did MTV – or those of us watching – know at the time that her most artistically groundbreaking work in the medium was yet to come.

Two things we did know at the time, however:

  1. Madonna’s insistence on sending Nikki Finn to collect awards on her behalf during this period was cute and everything, but mostly it just seemed…well…reductive.
  2. Madonna really liked that dress. But was it a dress?

Today in Madonna History: September 14, 1984

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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!