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Kylie Jenner Recreates Britney And Madonna's Iconic VMAs Kiss For Halloween

The makeup mogul and her best friend Stassie Karanikolaou dipped into the pop culture archives for inspiration.

Rise and shine from your post-Halloweekend slumber, everyone, because Kylie Jenner recreated a pop culture moment for the ages. 

The reality TV star was only about six years old when Britney Spears and Madonna broke the internet — before it was really even the internet — with their famous kiss at the 2003 MTV Video Music Awards. But icons recognize icons, so Jenner and best friend Stassie Karanikolaou pulled out all the stops to reenact the moment on Saturday night in impressive detail. 

The makeup mogul went as the Material Girl — slicking her hair back in a bun, wearing a form-fitting black ensemble and carrying a top hat — while Karanikolaou channeled the pop princess in a white bridal number. 

In an Instagram video, the two dance around to Madonna’s “Like A Virgin” before Karanikolaou-as-Spears tells Jenner: “Kiss me.” 

And so she does, but it’s only a brief peck — not likely to cause nearly as much conversation as Madonna and Spears’ lip lock, which went down as one of the most defining moments in award show history. 

While no one appeared to have dressed as Christina Aguilera — who, let us not forget, was also at the VMAs that year and also kissed Madonna on stage — Jenner laid that groundwork in a past Halloween. 

The 22-year-old rocked the look from Aguilera’s “Dirrrty” era for a night back in 2016, complete with assless chaps.

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Jenner seems to be making the most out of the holiday’s outfit opportunities this year, sporting head-to-toe black leather for some pre-Halloween festivities earlier in the weekend. 

She attended a J Balvin concert alongside friend Sofia Richie. The two seemed to have a night to remember, swigging tequila from the bottle backstage and running into musician will.i.am.

And since we’re dealing with the Kardashian-Jenners — there’s no family that takes this holiday more seriously — expect to see the costumes to continue throughout the week, because you know Kim isn’t about to be upstaged by her little sister. 

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