Armored with a sheath dress, Chanel Sunglasses and her signature bob haircut, Anna Wintour commands loyalty from legions of fashionistas the world over.

However, the iron persona of US Vogue’s editor-in-chief may have been punctured by a more… ehh… comical portrayal of her daily life at fashion’s stalwart magazine.

In a new one-man show “Ryan Raftery is the Most Powerful Woman in Fashion,” solo-performer Ryan Raftery lampoons the great Wintour à la Meryl Streep in The Devil Wears Prada.

Dressing as Wintour in drag, Raftery sings and dances to the hardships of running fashion’s most prestigious publication.

Naturally, the jukebox musical focuses on one of the darkest periods in Vogue’s history – the decision to put Kim Kardashian and Kanye West on this year’s April cover.

The show’s bio, via The Public Theatre, reads, “[Wintour’s] power and influence cannot be denied. But when she places a reality star and a certain rapper on the cover of her magazine, the backlash is harsh and for the first time, her credibility is called into question.”

The show, with dates of September 5, 12 and 19 at Joe’s Pub in New York, has been a wild success.

The talk of the town during New York’s Fall Fashion Week, several dates sold out, and Anna Wintour’s daughter Bee Shaffer showed up for opening night.

20to30, in an email interview, recently spoke to Ryan Raftery about the sellout success of his one-man show.



Q: Where did you get the idea to create this show?

A: The idea came from two places.
One: An interview Anna did with David Letterman in which he started with “I know nothing about fashion, but I know everything about you. Why is that?” I knew there was a show there at that point.
Then, I remembered running into Anna on the street two years ago. I said good morning to her, and she scowled at me.


Q: Any fear of Condé Nast backlash?

A: I WAS scared of Condé Nast backlash. I blocked friends who worked there on social media.


Q: Where did you find the wig?

A: The wig was found in Harlem. We went to about three different places asking for an “Anna Wintour wig.” Every single time they said, “Who?”
Then my friend, celeb stylist Jake Dingler, styled it and added the highlights.


Q: You received a surprise guest to one of your shows, Anna Wintour’s actual daughter! What was it like meeting her, and have you heard what the real Anna has had to say of your show?

A: I found out Bee Shaffer was coming the Friday before opening night. For a split second, I considered changing parts of the show that I thought she might find offensive, but then realized that she works as a producer on Seth Meyers’ show, so she must have a sense of humor.
She loved the show and Instagrammed a photo of us, calling me her “surrogate mother.”
I sent Anna flowers last Thursday but have yet to hear back. I assume she has a sense of humor about it.


Q: Though you play Anna with a great deal of jest, it seems you have a lot of respect for her. For what reasons should we all look up to Anna Wintour?

A: I have the utmost respect for Anna. She not only does her job extremely well, but she seems to LIVE her job. We never see Anna looking anything less than perfect. That was a huge part of the inspiration for my show (and the song I chose for the finale – Pink’s ‘Fuckin’ Perfect’).


Thomas Freeman is Texas-transplant and aspiring journalist trying (but often failing) to navigate New York City. A current NYU student, Thomas also writes articles and manages media content for 20to30.

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