VMAs most memorable NYC moments, from Madonna to Miley Cyrus

Some of the most memorable moments in the history of the MTV Video Music Awards have occurred right here in New York City.

Join us as we relive iconic Madonna moments, the infamous Kanye-Taylor mic grab and so much more, before the awards return to where they all began at Radio City Music Hall on Monday at 9 p.m.

Madonna, “Like a Virgin” — Radio City Music Hall, 1984

Before Britney strutted the stage with a live python, before Miley twerked with Robin Thicke, there was Madonna, writhing provocatively in a wedding dress.

The Queen of Pop shocked the world at the first VMAs, and set the tone for shows to come, when she emerged from a giant wedding cake clad in white lace and a “Boy Toy” belt buckle to perform her 1984 single “Like a Virgin” in a decidedly unvirginal manner.

The singer writhed, rolled on the ground and flashed her underwear for viewers — a display some in the industry thought would be the death of her career, according to Billboard. Well, the rest is history.

Fiona Apple, “This World is B——-” — Radio City Music Hall, 1997

When then-19-year-old Fiona Apple took to the stage to share some age-appropriate teen angst in 1997, she likely didn’t foresee it trailing her for years to come.

But two decades later, the singer’s unexpected flaunting of award show niceties, indictment of her own industry and call for viewers at home to be true to themselves — plus a Maya Angelou quote! — remains an iconic moment in music history. The fiery diatribe is meandering and the moment is awkward as audience members alternately cheer and fall into confused silence, but it seems authentically felt by Apple, who would go on to endure scathing mockery for the brief outburst. Anyway, she still managed to thank her mom, which is really the most important part.

Britney’s Snake Performance — Metropolitan Opera House, 2001

It’s hard to imagine any other performer sharing the stage with Britney Spears and stealing the show, but nearly two decades later we’re still talking about the pop star’s one-time coldblooded companion.

Halfway through Spears’ hip-shaking, jungle-themed performance of “I’m a Slave 4 U” at the 2001 awards, the singer famously retrieved a yellow python from a fellow dancer and draped it across her shoulders, twirling and strutting across the stage while holding the large reptile aloft. The moment is now iconic, but Spears has since said she regrets it, calling the stunt “scary” and “stupid.”

Madonna Kisses Britney — Radio City Music Hall, 2003

This one is special because it contains a tribute to another iconic VMA moment — Madonna’s 1984 performance of “Like a Virgin.”

Pop princesses Britney Spears and Christina Aguilera descend from a wedding cake in their own very early-2000s replications of their foremother’s lace wedding dress, “Boy Toy” belt buckle and all. Madonna emerges in head-to-toe black and a top hat.

After performing a medley of hits together, Madonna leans in and gives Britney a kiss. Madonna then swoops in on Christina, but few remember that detail all these years later — the Britney/Madonna smooch alone remains enthroned as one of the most shocking and memorable VMA moments of all time.

Kanye and Taylor Swift Mic Grab — Radio City Music Hall, 2009

It was the “Imma let you finish” heard ‘round the world.

Then-relative newcomer Taylor Swift was hardly the ruthless diva of “Look What You Made Me Do” when she was upstaged by Kanye West, who famously swiped the microphone from the country singer’s hands to suggest the moon man should’ve gone to Beyoncé. It’s surreal now to watch her genuine joy and awe at having won morph into genuine shock and embarrassment as the scene unfolds — but of course the ever-benevolent Beyoncé gave those minutes back to Swift. And anyway, juicier Kanye/Taylor drama would ultimately eclipse the award show gaffe in the years to come.

Miley Cyrus and Robin Thicke — Barclays Center, 2013

In which Miley Cyrus was upstaged by her own tongue.

This performance garnered a lot of pearl-clutching due to its over-the-top crudeness, but it wasn’t sexy so much as bizarre and vaguely disturbing. Who could forget watching the barely-adult Miley gyrate on a foam finger, aggressively thrust out her tongue, and twerk on the older Robin Thicke as he crooned his insanely problematic hit “Blurred Lines”? It’s unclear what kind of statement she was hoping to make, but she certainly got our attention!

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