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 back at some of the award show’s most iconic moments and outfits. And in doing that, it becomes 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
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The one that started it all. Madonna’s debut as “virgin” bride during the 1984 MTV Video Music Awards (the very first VMAs EVER) accomplishes two things: it puts Madonna on the map as Queen of Pop Music (if anyone challenges me on this, I will fight you), and establishes MTV’s annual award show as the place where water-cooler moments happen. The bride wore white, dripping in pearls and rosaries, and was tightly cinched in place with a “Boy Toy” belt.
1989: “EXPRESS YOURSELF” MADONNA
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Madonna debuted her “Express Yourself” single with its first live performance ever at the 1989 MTV Video Music Awards wearing a bustier, slouchy wide-legged railroad striped pants, and a magnifying glass necklace. On the beauty tip, baby Madonna’s sporting cropped curls and grown out roots presumably from her last film “Who’s That Girl?”
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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
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Madonna channels the French aristocracy in this iconic performance of “Vogue.” It’s with this hyper-theatrical performance that the bar is officially raised for all future pop starlets thereafter.
1993: MADONNA’S BERLIN ERA
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Madonna goes full-on Dietrich while she performs a cabaret version of the Girlie Show and song “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 white button-down, cummerbund and tie, along with black suit jacket (with tails naturally) and pants. Not bad, M.
1994: MADONNA AS FLAPPER
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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.
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She later shows up in a black, sleeveless sheath dress to present “Video of the Year.”
1995: MADONNA’S BLOUSE OF MANY COLORS
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Madonna’s silk blouse form the ’95 still puzzles me. I have no issue with the cleavage baring (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 Keidis 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 Ciccone during an interview with Kurt Loder.
1997: MADONNA AS ANNIE HALL
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No stranger to androgynous dressing, Madonna arrives with Guy Oseary to the 1997 MTV Video Music Awards like she’s channeling the iconic Diane Keaton character in a black jacket atop 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
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The late ’90s were full of new age mysticism and conspiracy theories. It’s funny in retrospect, but at the time (fourteen 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. 1998 introduced to “Ray of Light”, Madonna’s “Eastern enlightenment” album, the birth of Kabbalah Madonna, and her interest in Jewish mysticism. Her performance for that year featured her sporting dark straight hair, piles of gold jewelry, henna tattoos, and a black Indian sari during “Shanti/Ashtangi.”
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She later strips down to a white tank top during her hit “Ray of Light.” Check out those guns!
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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
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1999 was the year that Madonna received 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 her abdomen. (Also “Human Nature” Madonna, I’d like that black pleather catsuit please. Call me.) After examining the lineup, Madonna deadpans with “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 PROVACTEUR
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In a pre-Miley world, 2003′s award show was “The VMAs Heard Around The World.” In a performance given by Madonna, Britney Spears and Christina Aguilera, Madge not only cannibalized her proteges like a pop 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 in a top hat, black bustier, bodysuit, boots and a tuxedo jacket with tails.
But of course all everyone remembers is the kiss.
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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
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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. For the sake of transparency, I’m going to break a wall here. 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.
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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!
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