Madonna is set to make her return to the VMA stage this Sunday where she is the most nominated artist of the evening, with 13 nominations, and is scheduled to open the show and perform songs from her latest hit album Confessions II. This is the fifth time she will open the VMAs and the first time the queen of pop has performed at the event in 23 years. Which means that, yes, it’s been 23 years since the infamous kiss with Britney Spears (and Christina Aguilera, I guess?).

Aside from Britney, no other artist has made as much noise with their VMA appearances than Madge and given the extraordinary year she’s been having, now is the perfect time for her to make her return.

Madonna taking the stage at the VMAs has been teased for weeks and it is also expected that special guests will be joining her. This current album cycle includes collaborations with artists like Sabrina Carpenter, Kylie Minogue, Charli XCX, Stromae, Feid, and Martin Garrix just to name a few, so the possibilities are endless. Charli XCX has been confirmed as a presenter so we know she’ll be there – could we be getting a “Danceteria Afterhours” live performance?

Madonna’s first time at the VMAs was in 1984, with “Like A Virgin” and has since appeared on the show a whopping FIFTEEN times across five different decades. Her appearances have ranged from outrageous and scandalous, to heartfelt and emotional. Here are what I consider to be five of her most important VMA appearances over the years.

5. The Courtney Love Interview (September 7th, 1995)

The 1995 VMAs were as chaotic and star-studded as you would imagine a 90s award show to be. TLC were the big winners of the night and everyone from Michael and Janet Jackson to Whitney Houston and Bobby Brown was there. Basically, the epicentre of 90s pop culture in one evening. At the time, Madonna was in the middle of her Bedtime Stories album cycle. You know, the album that was meant to soften her image after the Erotica album made her American’s villain and chief corruptor a few years prior. Dressed in a demure (for Madonna) Tom Ford ocean blue blouse and black trousers, she certainly was rocking a softer look than her previous 1993 BDSM-inspired performance outfit. Yes, her bra was still showing but this is Madonna, that’s basically a nun’s outfit for her. She was a woman with a mission, and that mission was getting back into America’s good graces – and it worked. She won Best Female Video that night for “Take A Bow” and presented an award to Dr. Dre; but in true Madonna fashion, her signature attitude found a way to make headlines even with her intentional laid-back demeanor. M’s live post-show interview with MTV host Kurt Loder that was initially just your standard catch-up was interrupted by a messy Courtney Love who crashed the interview by throwing her compact from the sidewalk at Madonna. Madge who was clearly disturbed by the interaction BEGGED Kurt not to let Courtney up to the interview stage and even gave us the now iconic like “Courtney Love is in dire need of attention right now” and the very shady “and lots of available drugs” when responding to Courtney’s favourite moments of the evening and after-parties. Yikes. Icy and tense yes, but MTV wasn’t about to pass up the moment. After a few awkward words between both ladies and M’s clearly irritated expression, Madge’s publicist came to her rescue and escorted her out. This exchange came only one year after the tragic death of Kurt Cobain, a time when Courtney was a tabloid obsession. It remains one of the most shared unscripted VMA moments and a viral moment before the term “viral moments” even existed.

4. “Express Yourself” (September 6th, 1989)

1989 was an illustrious year for Madonna. She released her iconic album Like A Prayer, lived through a very public scandal with Pepsi and managed to piss off the Vatican – all in a matter of months. Her performance of “Express Yourself” was not only her live debut of the song, but it also was her first performance at the show since she shocked the world in 1984 when she performed “Like A Virgin” (more on that later). If you ask some fans, they might consider this performance of “Express” to be her best in VMA history. There are whole opinion pieces on why that is – and I understand. It has everything that an iconic Madonna performance should have. First the iconic trio of M, Donna, and Nicki on that stage is diva history. The cone bra, the chair routine, the LIVE VOCALS, the confidence. It’s Madonna at her greatest and if she were any other artist this would likely be at the top of the list, but Madonna is an artist who continues to top herself – and she would do that once again the following year. 

Her evening didn’t end at her opening performance though. She won the Viewer’s Choice award for “Like a Prayer” and presented George Michael with the Video Vanguard Award. Madonna had won the very same award back in 1986 when she was only four years into her mainstream pop career. This is especially fitting when taking this year’s upcoming show into account since there’s a planned George Michael tribute performance with RAYE, Teddy Swims, and Sombr set to take the stage. M isn’t a part of it so it will be nice to see her reaction during the show. I do love a connecting thread.

3. The Kiss (August 28th, 2003)

The shot of Madonna and Britney Spears kissing is probably in the top three most replayed VMA moments – ever. I truly can’t remember a single year since this happened that I haven’t seen some sort of promo using this shot. It’s exactly what the VMAs stood for: shock value, music history, unpredictability, and most important of all – scandal. This was the 20th anniversary of the VMAs so having Madonna re-create the performance that put the show on the map was a no-brainer. Originally, Madonna was going to be performing with Britney and JLo, but Jenny had to drop out. Side bar: no shade to Jennifer, but I can’t imagine her giving much to this performance. P!nk and Gwen Stefani were also asked to take part. None of those make any sense to me. It just HAD to be Christina, it wouldn’t have been as important without her. Britney and Christina were THE pop princess daughters of Madonna and Janet, at least at the beginning of their careers. The rivalry between the two made it too perfect. Of course, as with everything between Brit and Xtina, Britney took the spotlight on this one. A common trend that still goes on to this very day. When you think about it, it truly was wild in 2003 to see two women kissing on television. Especially when it’s America’s sweetheart, Britney Spears, and the queen of pop, Madonna. The tabloids plastered this moment for months afterward, and Britney had to answer to some pretty crude questions regarding what happened. Madonna, on the other hand, was simply playing the role that she knows how to do best: mother.

2. “Like A Virgin” (September 14th,1984)

This is the performance that put the Video Music Awards on the map. The moment that turned this show into appointment television, a yearly EVENT. Madonna opened the first ever VMAs performing “Like A Virgin” – a song that she hadn’t even released yet. She performed in a wedding dress styled by French designer Maripol, paired with a belt that proudly bolstered the words “Boy Toy” in all caps and a low-cut bustier. She emerged from a 17-foot tall wedding cake before making her way down the stairs and eventually unintentionally flashing the entire audience. She has said in later years that she actually had lost a shoe and was looking for it and decided to improvise. It’s art. What at first was considered to be a career killer wound up becoming one of the most unforgettable moments in both VMA and pop culture history. It’s the first real taste that the greater public got of what kind of artist Madonna really was. This performance made both her and MTV as a station a household name and it changed the way female pop singers perform forever. Madge was unapologetic about all of it, and took every hit in the name of her artistic integrity. Today’s cultural language has loosened the meaning of the word “iconic” and it tends to get thrown around, but in this case, Iconic is the ONLY word to use.

1.“Vogue” (September 6th, 1990)

Aside from being the queen of pop, Madonna has also earned the title as a queen of re-invention. Every album, every video, every single had a distinct look and concept. What was presented on the VMA stage in 1990 is nothing short of a masterpiece. An inexplicable portrayal of what an artist can really do with pop music. The Marie Antoinette-inspired performance featured Madonna wearing the very same dress that Glenn Close wore in Dangerous Liaisons. It was all 18-century French fashion pieces from the powdered wigs to the satin coats that her legendary troupe of male dancers wore. This performance was the final one where Madonna performed with her dance crew from the Truth or Dare film and the legendary Blonde Ambition Tour. Up until that point, performances at the awards show had never been as elaborate. Even Madonna’s own performances before then were fairly simple – just choreography and a set piece or two. This was its own standalone production, a production where it was clear that the focus was on performance and turning art into reality rather than singing. She didn’t even wear a microphone, it was clear that this was lip-synched. But that wasn’t the point, it was intentional. She was bringing a music video to life, a completely new concept. She further re-invented what a televised live performance could look like. “Vogue” is one of her biggest and most important hits, but this period in her career also holds that very same weight. A visionary always, this is peak Madonna as she will always be remembered. Yes, she has continued and continues to create incredible moments in her art, but this performance is the absolute greatest that she has ever been.

Photo credits: James Colburn/Globe Photos/ZUMA Press Wire/Shutterstock

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