Madonna’s Best Award Show Performances


If we could crown someone monarch of award show musical performances, Madonna would be the rightful queen. In 1984, she stormed into the mainstream with a legendary rendition of "Like A Virgin" that made both herself and the nascent MTV Video Music Awards icons of pop culture. For 35 years, she's used dance, costume, presence and sly wit to continually subjugate audiences and dominate conversations — in her youth with a sort of pluckiness, and in her elder years with a smirky kind of who-you-think-invented-this swagger.

A creature of many faces, Madonna will debut her Madame X persona on stage with Maluma as the pair performs the bilingual collaboration "Medellin" at this year's Billboard Music Awards Wednesday (May 1). She graced the BBMA stage alongside Stevie Wonder in 2016 for a Prince tribute, but this is Madge's first time doing her original thing for our big night. In preparation for what will surely be a cinematic moment, we take a look back at her greatest award show performances.

"Like A Virgin" at the 1984 MTV VMAs 

All hail the dry-hump felt 'round the world. Pop stars were freed of their pretty princess crowns as Madonna performed this fully-clothed strip-tease for dirty minds of all kinds. It was salacious, sensational, and in retrospect, really freakin' simple. It just goes to show you don't need anything fancy and expensive to change the world. All you need a determination, courage and a dash of panache.

"Express Yourself" at the 1989 MTV VMAs

Madonna is beautiful, sure, but she's also strong, and she's always loved to toy with expectation. She's put androgyny under a spotlight more than once, and for the 1989 VMAs, she mixed lingerie and business men in one powerful performance. Her voice booms strong as she demands strength from women around the world to stand up for themselves against tepid romanticism and social expectation, and it's pretty dope the way she puts the mic in her bra and kicks some killer dance moves.

"Vogue" at the 1990 MTV VMAs

Does "Vogue" have the "ha" beat? No, but it's still a classic, and so is this live rendition. She stunned audiences in French Rococo fashion — powdered wig, heavy white face makeup and all. She was flanked on all sides by beautiful people of color who came to serve snotty Aristocrat realness for middle American audiences to drool over. Tens across the board; yes, please and thank you.

"Sooner or Later" at the 1991 Oscars

The Oscars remain a stuffy occasion livened up here and there by the occasional misreading of a best picture winner and some political commentary. Usually, the musical performances are powerful affairs that rely on singing talent, but Madonna put a little color in the gold man's cheeks with a classy-meets-brassy seduction. She started the song, nominated that year on the Dick Tracy soundtrack, with her back to the audience and gave her round behind a nice caress. Her breathy roar is also on great display.

"Shanti Ashtangi / Ray of Light" at the 1998 MTV VMAs

Dare ye not claim Madonna as unenlightened. In the late '90s, she studied ancient Indian traditions and discovered a personal mantra, which she then penned into the song "Shanti Ashtangi." She shared that mystical light with the world before going into the title track from her seventh studio album, and that intro choreographed with traditional Indian dance is definitely the best part — not that Lenny Kravitz playing guitar on "Ray of Light" is anything to snub.

"Like A Virgin/Hollywood/Work It" at the 2003 MTV VMAs

You know you're a legend when you can be self-referential and everyone applauds. Madonna passed the baton to her conceptual children, Britney Spears and Christina Aguilera, in this much-talked-about moment of the early aughts. Of course, there's the obvious nod to the 1984 performance with the fashion and the cake, but don't miss Britney sticking the mic in her bra a la "Express Yourself." Please take note of everyone in the crowd – their reactions, what they're wearing. Why is Missy Elliott on stage to perform a song that has nothing to do with Madonna (other than that Gap ad)? Because she's a badass. Don't question it. This is greatness.

"Hung Up" at the 2006 Grammys

Without question, "Hung Up" is one of the best Madonna songs and outright dance-pop songs ever recorded. Watching Madonna dance around with all that leg is always cool, but what really blew minds was the way she walked behind the hologram of Gorillaz bassist Murdoc. She then walks to another stage and explodes in electroclash disco madness. All her backup dancers are amazing, too. Respect. 

"Same Love / Open Your Heart" at the 2014 Grammys

In 2014, Macklemore and Ryan Lewis took home the Grammy for album of the year with their conscious and progressive LP The Heist, but before the rapper-producer duo was handed the big prize, it made an even bigger statement by helping to marry an array of same sex couples on live television. At the time, same sex marriage was not yet legal across the country, but it was in the 2014 Grammys' host state of California. Queen Latifah acted as officiator, and once the kisses were sealed, Madonna serenaded the happy couples with "Open Your Heart." Don't be embarrassed. We're crying, too.