The New York Comedian Doing Martha Stewart Drag

Ryan Raftery's story begins like so many: an aspiring Broadway star struggling to find work, but frustrated with the audition process and his day job. Luckily, that's where the traditional struggling actor narrative ends--instead of letting the industry get him down, Raftery found a way to turn the world around him into comedic gold, starting by impersonating Vogue's indomitable Anna Wintour, whom he had learned about while working for Coach.

When Wintour's daughter attended opening night of Raftery's cabaret about her mother, he was catapaulted into international spotlight, and what has unfurled since is a story that involves everyone from Bravo's Real Housewives to Snoop Dogg.

With his latest show, Raftery tackles one of pop culture's most unique and recognizable names: the domestic icon that is Martha Stewart. The Rise and Fall (And Rise) of Martha Stewart opens Monday, August 7 at Joe's Pub, with five New York performances before it travels to Los Angeles.

We sat down with the creator, writer, and star of the cabaret to hear the full journey of his ascendance from aspiring musical theater actor to celebrated celebrity impersonator.

OUT: How did you decide to start doing cabaret shows about celebrities?

Raftery: I'm from New York and lived in Los Angeles for a few years. I'd done some TV, but all I really wanted to do was work on Broadway. So I moved back and magically thought I would have this career on Broadway. I started auditioning, and wasn't getting things, and a lot of people were telling me it's because I look like a tenor, but I'm a baritone. Long story short, in order to get on stage I started doing cabaret, and I did a couple of shows that were autobiographical. I started building this tiny fanbase, but soon I found I had nothing else to say. There was no more life experience to mine.

Why'd you choose Anna Wintour as your first subject?

At the time I had a day job working for Coach in Public Relations. It was 3 years ago, when they started showing at fashion week, and I just remember hearing everybody in the office saying the name "Anna" over and over again. "Anna won't like that..." "Anna might come for 15 minutes or she might send someone else..." I obviously knew who they were talking about, and the legend that surrounds her, from The Devil Wears Prada, and I started googling her and finding out more about her. Then I had to help bring the collection to the Vogue offices, because Anna wasn't coming to their presentation. I wasn't high enough level to be in the meeting, but I got to go to Vogue, and just the way the air was disturbed in that office, knowing she was around. It was literally like the beginning of The Devil Wears Prada, when you just see people running. It was really intense. I realized I can insert a celebrity into the place where I'd insert myself in a cabaret.

How'd the Anna Wintour show get received? Did she see it?

The Anna Wintour show became a huge success because Anna's daughter came opening night. My shows had gotten tiny amounts of press before, but nobody really cared. There are so many actors in town who do cabarets. People were entertained, but there was certainly never a chance for international coverage. But Anna's daughter, when she came to the show, came backstage and Instagrammed us, and that photo went literally around the world. It got traction everywhere--Brazil, Portugal, Canada... I got contacted by a French magazine who sent a photographer to shoot me, and they did a whole 3 page spread. It was truly life-altering. And I only had 3 shows planned at Joe's Pub, so I added midnight shows, and every single one of them sold out. In my old shows, I'd come out onstage and recognize a lot of people in the audience, but now I didn't know anyone. Which is obviously the goal. That show went to Los Angeles, then San Francisco. Anna's daughter took video and showed it to Anna, who was amused by it, so a lot of people at Conde Nast knew about it. And I realized I needed to keep doing this, impersonating celebrities.

And after Anna you tackled Andy Cohen?

In the Anna Wintour show, there's a song about her almost getting fired for putting Kim Kardashian and Kanye West on the cover, and I got to thinking about how reality TV, for better or worse, affects us. Everyone has their opinion on it. And when it comes to reality TV, there's really only two producer names that come to mind immediately, and that's Ryan Seacrest and Andy Cohen. It didn't take me long to realize doing a show about Ryan Seacrest would be really boring. So I was doing research on Andy, and saw an interview where he was doing a speaking tour with Anderson Cooper. And somebody in the audience asked, "Did you two ever date?" And Andy said, "Oh, we went out on a date once, but neither of us were into it." As soon as he said that I called bullshit. Who would not be into gorgeous, rich, famous Anderson Cooper? His mom is Gloria Vanderbilt--he owns a firehouse in the village. I'm not saying everyone needs to be instantly attracted to an intelligent, rich famous person. But there was a show there. Andy is a television executive who gave himself his own talk show. That's something I felt very interesting and telling. He wanted to be famous and created a whole genre of celebrity who does absolutely nothing.

Did Andy react to the show at all?

When I was doing the Anna Wintour show, I'd already decided I was going to do Andy next. And he actually invited me to Watch What Happens Live! to be the bartender, as Anna Wintour. When he came to say hello to me before the show started, I had the opportunity to tell him to his face, "I'm doing you next." And he instantly had this look of panic on his face. He didn't come to see the show, but he sent flowers on opening night. And a lot of Housewives came to the show. But it would have been a little weird for him to come, because everyone would be watching him watch the show.

So Anna, then Andy... then Martha?

I always loved the idea of a trilogy. So I made a list of people to do, and pretty quickly I knew it had to be Martha. I'd admired her from afar because of everything she knows how to do, but the prison element gives the story something so Shakespearian. I call the show The Rise and Fall (and Rise) of Martha Stewart, but she's never fully rebounded from going to prison. She's still relevant because of her show with Snoop, and she was just nominated for an Emmy, but the height she reached in the late '90s and early aughts... She was really targeted for being a successful woman, and made the poster child for corporate greed, even though Enron, and a lot of that stuff was going on at the time. She really paid a big price financially and otherwise. But for me as a comedian, how funny would it be to do a musical number of Martha in prison? So what I've tried to do is create a show anybody can come see, even if you're not a huge fan of Martha. I think she's the most famous subject I've ever tackled.

What can you say about the Martha show?

The show opens with Martha on the day she's going to prison, and she's saying goodbye to her chickens, and she's singing to them, and then we go back in time to when she's 15, and then to when she's 75, which is today. It's been an incredible experience researching her. It's weird to know so much about somebody you've never met. So much of Martha's life is so heavily documented. And for this show I'm going full drag, which I've never done before.

Are the shows pretty accurate to the subjects lives then?

The skeleton of the show is 100 percent true--and the way I flesh it out can sometimes be for comedic effect. Martha is the first origin story I've done. If you were to put up a timeline of her life, I really do hit all of the major achievements--she was a teen model, and she went to Columbia University. She gets married. She has a kid. She moves to Connecticut. She becomes a stock broker. She starts a catering business. She writes a book. She works with K-Mart. She gets a magazine. She gets a TV show. She goes to jail. She does a show with Snoop Dogg. That's all in the show. But this show ends in a completely nonsensical way. It's meant to be very funny and ridiculous.

Do you have other celebrities you really want to impersonate?

I'm a really big fan of Woody Allen. Woody Allen always said that after he met Diane Keaton, he started to see the world through a woman's eyes. And he likes writing for women a lot more. I do too. I'd love to do a musical about Mariah Carey, but the weird thing about doing a musical about a musician, is it creates this weird problem of, "Do you use their music?" And if I do, I have to use all of it. And that's limiting for me. In the Martha Stewart show I have all different genres--there's a song from Moana, there's a Beyonce song, there's Adele. I really want to do a show about Andy Warhol. I really want to do one about Blue Ivy.