The Wildest Met Gala Moments Of All Time

We’re only a few fleeting weeks out from this year’s Met Gala which means fashion, fashion, a rare Anna Wintour spotting, and more fashion. Though the night is focused on neck-snapping looks like Rihanna’s sparkly pope cosplay and Zendaya literally glowing as Cinderella, the carpet also serves as a much-needed opportunity for celebs to get very silly in very expensive clothing. If I spent weeks of preparation and hours in a chair with a crew of people working to make me hot, I’d probably want to show off too. That’s the beauty of Anna Wintour’s exclusive night out. Unlike the Oscars or the Grammys, when stars are worried about their acceptance speeches or musical performances or on rare occasions about getting slapped, The Met Gala is a purely visual experience that allows artists to escape the pressure of seriously representing their craft to masquerade as someone else entirely for a night, instead. Without further ado, let’s relive the wildest Met Gala moments, my favorite night to sit at home and critique millionaires’ appearances from my couch.

Doja Cat Went Full Feline

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Doja loves to get weird, but last year’s prosthetic transformation into Karl Lagerfeld’s cat Choupette with a cat-eared Oscar de la Renta beaded masterpiece to match was arguably her best work yet.

Princess Diana’s Night Out

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After her historic divorce from her ex, The People’s Princess had to keep a low profile to avoid the constant headlines fashioned after her every movie. That is until she decided to step out in a timeless John Galliano blue number at the 1996 Met Gala. Is this the original revenge dress?

Zendaya Makes A Wish

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Zendaya (who is one of this year’s Sleeping Beauties co-chairs) made the night magical in 2019 when her fairy god-father Law Roach granted her a wish including a visible “poof” from his wand. I know they already released a live-action Cinderella, but can we make Zendaya the next Disney darling pronto?

Emma Chamberlain and Jack Harlow

While my most quoted Emma interview moment is her “mama” interaction with Gigi Hadid, who could forget when Jack Harlow accidentally told Emma he loved her and she returned the gesture?

Kim Kardashian Turned into a Targaryen

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A huge part of the night’s fun revolves around trying to guess which celeb just stepped out of the identical black SUVs lining up at the curb, as they often look totally unrecognizable. Before the public realized she was wearing a preserved Marilyn Monroe original, Kim Kardashian already had the internet spiraling when she showed up with Danaerys Targaryen blonde locks overnight.

J.Lo and Ben’s Covid Safe Kiss

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Since their reunion in 2021, Bennifer has remained the couple that keeps on giving. Their passionate (and possibly unnecessary) masked-up MO was one of many publicity stunts the couple makes it hard to look away from. Never change, you two.

A$AP Rocky’s Parkour Moment

Mr. Robyn Fenty got creative when he found himself on the wrong side of the Met steps in 2023. Stuck amongst the crowd of fans, A$AP cut the line by jumping over a barricade into the event, accidentally bumping into a fan in the process. On the bright side, that girl has a great story to tell now, so lowkey win-win scenario.

Jaden Smith’s Big Chop

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I stand by the theory that if Jaden and Willow Smith had to pay rent, they’d be the biggest artists of their generation. For now, we’ll have to take their kernels of experimentation as they come, like when Jaden showed up to the 2017 Gala holding the dreads that once lived on his head in his hand.

Cardi B and Nicki Minaj Make Up

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Cardi and Nicki’s ever-evolving feud had a peaceful moment at the 2018 Met Gala where fans were surprised to see the battling divas talk it out in front of the Met steps months after their rumored altercation at a NYFW afterparty.

The Rule-Breaking Bathroom Selfie

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Never one to play by the rules, Kylie Jenner decided to skirt the event’s strict “no photography” policy to give the little people at home a chance to feel involved with a bathroom selfie. Time’s up jump scare warning for this one, folks.

Lady Gaga’s Magical Shrinking Outfit

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Gaga looked camp right in the eye with her hot pink Brandon Maxwell gown in 2o19. By the time she had unrobed from the voluminous ball gown into a matching set of lingerie, it was impossible not to say “ooh la la.”

Say hello to Frank Ocean’s little friend

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The Orange Channel artist decided to go green at the 2021 Met Gala with a neon robot babydoll as his red carpet companion. Creepy? Yes. But let’s all just be happy Frank showed up.

2 Chainz Proposal

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While celebrating the Heavenly Bodies collection, 2Chainz decided to make Keisha Ward his forever by dropping down on one knee on the red carpet. I mean, I just got a text back, but that’s cool too.

That time we thought Jason Derulo fell down the stairs

Jason Derulo (always to be sung in his signature vocalization, of course) was not in the state of New York when someone else tumbled down the stairs in a white tux at the 2015 Met Gala. Still, the internet somehow deduced it was him anyway and thus my favorite urban legend was born.