Anna Wintour and Amy Schumer swap jobs for a day. There's a clear winner.


Open scene: Anna Wintour and Amy Schumer face to face in the Vogue office, somewhere near the top of One World Trade Center.

Schumer is Vogue‘s July cover star— her feature story is definitely worth setting aside half an hour for— and at the start of this video, they’re just talking business.

Inevitably, they get into a polite one-upsmanship. “I could never do what you do,” Wintour says insincerely to Schumer. It’s interesting— it must actually be a lot of fun to be Anna Wintour. She’s been in her role as editor-in-chief at Vogue for nearly 30 years, and is clearly yet to miss a beat. She’s the queen of the icy fashion stereotype, and she’s in on the joke. The woman is a genius at playing herself.

Anyway, “I could never do what you do,” Schumer replies equally insincerely. Because that’s the thing, no one thinks their job is easy. Are there exceptions to that? Sure. But they’re few and far between. Almost everybody thinks their job is harder than everyone else’s. But politely, we don’t mention it, and keep our eye-rolls internal when our friend tells us again about her scheduling dramas.

Schumer and Wintour, not so much. Within seconds, they’re throwing down. Then they challenge each other to swap lives.


Schumer hams it up. First up, by literally failing to walk in Wintour’s (presumably very precarious) shoes.

You can watch the full clip here. Post continues after video.

Perched on a chair, juggling a dangerously large coffee and some oversized shades, she “picks” outfits, trying and failing— much to the disgust of her weary assistants— to distinguish between two magenta sequined cardigans.

Schumer is famously unfussed about fashion IRL. In her Vogue cover story, she explains she’s not necessarily against it, she just doesn’t really give it a lot of attention. “I think that there’s a misconception in fashion that everybody wants in,” she says. “I am very happy to remain out.”

Back to the video, and we flash to Wintour at one of New York’s famous stand-up venues, The Comedy Cellar, which I really, really hope is a thing that actually happened. She seems to take it entirely in her stride— but then, that’s kind of her thing, isn’t it?

In the spirit of no spoilers, we won’t reveal the winner here. But the ending does involve an actual mic drop.

This post was originally published on Flo and Frank, and has been republished here with full permission. 

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