Not sure if you’ve heard, but it’s VMA season again. To prep for the 2014 Video Music Awards we’re taking a look at some of the show’s most iconic moments and outfits. In doing so, it became clear that there’s pretty much no one more intrinsically tied to the VMAs than Madonna. Let’s take a look back at Madonna’s most iconic moments.
1984: “LIKE A VIRGIN” MADONNA
The one that started it all. Madonna’s debut as a “virgin” bride during the 1984 MTV Video Music Awards (the very first EVER) accomplished two things: It put Madonna on the map as Queen of Pop (if anyone challenges me on this, I will fight you) and established MTV’s annual award show as the place where water-cooler moments happen. The bride wore white, dripping in pearls and rosaries, and the dress was tightly cinched in place with a “Boy Toy” belt.
1989: “EXPRESS YOURSELF” MADONNA
Madonna debuted the “Express Yourself” single by performing the song for the first time at the 1989 MTV Video Music Awards. She wore a bustier; slouchy, wide-legged, railroad-striped pants; and a magnifying glass necklace. On the beauty tip, she’s sporting cropped curls and grown-out roots, presumably from her last film Who’s That Girl?
For contrast, we’ve provided a photo of Madonna with a top on, which she wore while accepting the Viewer’s Choice Moonman in ’89. Because really, when hasn’t Madonna looked great in menswear?
1990: MADONNA ANTOINETTE
Madonna channels the French aristocracy in this iconic performance of “Vogue.” It’s with this hyper-theatrical performance that the bar was officially raised for all pop starlets thereafter.
1993: MADONNA’S BERLIN ERA
Madonna goes full-on Dietrich while she performs a cabaret version of the Girlie Show, singing “Bye Bye Baby” at the 1993 MTV Video Music Awards. Controversial opinion: This might be Madonna’s most flawless look. A top hat paired with a white button-down, cummerbund, and tie, along with a black suit jacket (with tails naturally) and pants. Not bad, M.
1994: MADONNA AS FLAPPER
Madonna shines in an elaborate seafoam green dress with chain detail and finger waves during the 1995 MTV Video Music Awards. Peep the dark smoky eye and vampy nail polish. Hella ’90s, y’all.
She later shows up in a black, sleeveless sheath dress to present Video of the Year.
1995: MADONNA’S BLOUSE OF MANY COLORS
Madonna’s silk blouse here still puzzles me. I have no issue with the cleavage (because she’s perf always), but rather I can’t tell what color it is. In some lights it’s a beautiful blue, as in this photo with Anthony Kiedis of the Red Hot Chili Peppers. Other times, such as when she’s presenting, it appears to be a sea-glass green. Who knows? Maybe I’m still shaken up because this is the year that M. went head-to-head with Courtney Love in a hilarious showdown after the latter threw a MAC compact at Ms. Ciccone during an interview with Kurt Loder.
1997: MADONNA AS ANNIE HALL
No stranger to androgynous dressing, Madonna arrives with Guy Oseary to the 1997 MTV Video Music Awards looking like she’s channeling the iconic Diane Keaton character in a black jacket with a white blouse, tie, and high-waisted maxi skirt. What makes this extra funny is that Madonna as school marm is the presenter chosen to announce Prodigy at the ’97 VMAs.
1998: KABBALAH MADONNA
The late ’90s were full of new age mysticism and conspiracy theories. It’s funny in retrospect, but at the time (14 years ago) we thought the world was going to end in 2000. Y2K was a thing, y’all. Even Madonna wasn’t immune to this. In 1998, she introduced us to Ray of Light, Madonna’s “Eastern enlightenment” album, the ergo the birth of Kabbalah Madonna. Her performance for that year featured her sporting straight, dark hair, piles of gold jewelry, henna tattoos, and a black Indian sari during “Shanti/Ashtangi.”
She later strips down to a white tank top during her hit “Ray of Light.” Check out those guns!
Her red carpet look varied slightly from her performance outfit in that she wore red sequined pants and a seriously shiny overcoat. Also, some better detail on her henna hand tattoo.
1999: MADONNA AS TRIBUTE
This was the year that Madonna received a tribute in the form of half a million drag queens dressed in each of her iconic looks from music videos past. Personal favorite? The queen dressed as “Bedtime Story” Madonna, who has fake doves floating from the abdomen. (Also, “Human Nature” Madonna, I’d like that black pleather catsuit, please. Call me.) After examining the lineup, Madonna deadpans, “All I have to say is it takes a real man to fill my shoes.” And how! What was M. wearing? Black trousers, heels, and a shirt coat with tails.
2003: MADONNA AS AGENT PROVACATEUR
In a pre-Miley era, 2003’s award show turned out to me the VMAs seen round the world. In a performance by Madonna, Britney Spears, and Christina Aguilera, Madge not only cannibalized her protégés like pop’s black widow, but also referenced previous VMA performances of hers, notably her 1984 debut and her Weimar-moment in 1993 during the “Like a Virgin”/”Hollywood” medley. Brit and Christina wore matching white bridal gowns, veils, and “Boy Toy” belts while Madonna stomped the stairs like Gary Cooper in a top hat, black bustier, bodysuit, boots, and a tuxedo jacket with tails.
But of course all everyone remembers is the kiss.
The Queen Mother looked downright demure prior to and immediately after the performance in a pleated and belted black dress with cap sleeves, and pointy black boots. Note the Kabbalah bracelet still on her wrist.
2009: MOURNFUL MADONNA
Here Madonna poses in the press room at the 2009 MTV Video Music Awards at Radio City Music Hall in a black wrap dress and boots. She wore minimal jewelry to the proceedings. The 2009 VMAs were a somber occasion. The music community was rocked with the untimely loss of one our greats. There was a beautiful tribute for Michael Jackson from top choreographers and his sister Janet.
The memorial also included a tearful speech from Madonna, the only person who might be considered Michael’s contemporary in pop music. The singer wore a zippered black jacket and skirt, and her speech was beautiful and heartfelt. If nothing else, Madonna was a consummate class act during the emotional moment.
And that rounds out our fashion recap of Madonna at the VMAs. I don’t know about you, but I am living. Oh, and did we forget to mention, it’s Madonna’s birthday today? Happy birthday to the Artist with the Most VMA Wins in History™. It’s true, homegirl has 20 (see fact #28). HBD, Queen of Pop/Queen of the VMAs!