Madonna's Greatest VMA Moment Was an Accident
This Sunday, September 27, Madonna opens the MTV Video Music Awards at the Peacock Theater in Los Angeles. It is her first performance at the show in 23 years, and she walks in as the most nominated artist of the night, with thirteen nods: eleven in the first wave in August, and two more when the fan-voted categories were added last Friday, September 18. Snoop Dogg hosts, and the show airs live on CBS, with MTV and Paramount+ alongside. Nirvana collect the Video Vanguard Award the same night, which is a story for another page.
She has sung on that stage more often than people remember ("Causing a Commotion" beamed in live from Italy in 1987, "Express Yourself" in 1989, "Bye Bye Baby" in 1993), but four performances are the ones fans still argue over: Like a Virgin on a wedding cake in 1984, "Vogue" in Marie Antoinette finery in 1990, a sari and Lenny Kravitz's guitar for Ray of Light in 1998, and the kiss in 2003. So before she tries to top herself, we should settle which one she has to top, counting down from fourth.
4. Ray of Light, 1998
The night belonged to her anyway. The "Ray of Light" video won five awards at the 1998 show, including Video of the Year, her first win in that category. On stage she started with "Shanti/Ashtangi", a Sanskrit chant, with black hair and a sari, before Lenny Kravitz walked on with a guitar and tipped it into "Ray of Light".
It is a good performance of a great song, and it is last because it is the only one that people remember mostly for the argument afterwards. The World Vaishnava Association said she had offended Hindus by wearing a sacred Hindu mark on her head while simulating a sex act on stage; her camp said she had meant no insult. The music was the reason to be there, and the staging never matched it.
3. The kiss, 2003
This is the famous one: in 2008, MTV News named it the number-one opening moment in the show's history. Britney Spears appeared atop a giant wedding cake in a bridal gown singing "Like a Virgin", Christina Aguilera joined from behind the cake, and Madonna emerged from the cake in a black coat and hat for "Hollywood", from American Life, and kissed them both on the lips. Missy Elliott stepped out of a wedding chapel halfway through for "Work It".
The case against it starts with the staging. The best idea in the number is a quote of 1984, and Madonna spends the opening stretch as a guest at her own tribute. Entertainment Weekly's Brian Hiatt called the kiss "an indelible MTV moment" and, in the same sentence, "as meaningless as it was entertaining". Madonna's own gloss, that she was "passing my energy on" to Spears, "like kind of a mythological fairytale", makes it sound like a handover. That is what it was, and a handover is not a peak.
2. Vogue, 1990
The purest piece of stagecraft on the list. Madonna and her dancers came out in 18th century fashions inspired by Marie Antoinette, played the whole thing as a costume farce full of innuendo, and at one point she flipped open her enormous skirt so a dancer could crawl in one side and out the other. Rolling Stone later ranked it the sixth best performance in the history of the show, and biographer J. Randy Taraborrelli wrote that it raised the standard for everyone who followed. The song was the first single from I'm Breathless, and the video won Best Direction, Best Editing and Best Cinematography that night.
If you want the best performance as a performance, this is it. It loses only because everything it does, 1984 made possible.
1. Like a Virgin, 1984
The first VMAs, Radio City Music Hall, September 14, 1984. Madonna had wanted a live Bengal tiger; MTV said no. So she appeared atop a 17 foot wedding cake in a white bridal gown with a bustier, rosaries, lace gloves and a belt buckle that read BOY TOY. On the way down the steps a shoe slipped off, and instead of stopping she dove to the floor and rolled, and the dress rode up on live television.
Backstage, her publicist Liz Rosenberg was told her career was "over before it started". Her manager Freddy DeMann remembered the same worry. Meanwhile, watching from behind the curtain, the designer Maripol saw journalists rushing to find out who the girl rolling on the floor was. Rolling Stone compared its importance to the Beatles on Ed Sullivan, and Billboard and Slant have both ranked it among the greatest performances in VMA history.
That is why it wins, and by a distance. The 2003 kiss quotes it outright, and the 1990 skirt trick would not exist without it. Every VMA opener since, including the one she plays this Sunday, is measured against a moment that happened because a shoe came off and she refused to look caught. The show became the place where things like this happen because of her, on its first night.
What she needs on Sunday
Beating the cake is not really possible, because the thing that made 1984 great was that nobody knew who she was yet. So the bar to clear is 2003: one image people are still describing two decades later, with Madonna at the center of it this time, not handing it to someone else.
She has the material. Confessions II: The Film is up for Video of the Year, and she is also nominated for Song of the Year for "Bring Your Love" with Sabrina Carpenter. What she does not need is a medley of the hits or a parade of younger guests. The 1990 lesson is the useful one: pick one song, commit to one absurd visual idea, and play it straight. If Sunday ends with a single picture that is everywhere by Monday morning, she will have beaten 1998 and 2003, and the cake will still be sitting at number one.
Before Sunday
Queue the four records behind the four performances, in our order, then the two films that show what the cake made possible: Desperately Seeking Susan, the 1985 comedy that arrived while the cake was still news, and Madonna: Truth or Dare, the documentary of her 1990 Blond Ambition tour, shot the same year as the Vogue night.
