It's the first time Raftery has mined a political personality for a show, and he says it feels like a natural progression considering the current landscape: "The thing that’s fascinating now is that politics has always been a form of entertainment, but now it is entertainment, not just a subset of it, because of what we have going on in the White House right now and the way that [Donald Trump] acts like a petulant child, the way that he uses social media. It's literally show business, and it's really scary."
But he's quick to say that his goal is not to frighten. "My number one goal is to make the audience laugh. If they’re thinking, too, that’s a great thing," explains Raftery, adding that his preparation for this show is much different than the others. "Ivanka is a girly girl, so I’ve never really had to prepare physically for a role like this before. Like costume-wise, learning how to walk in heels. The makeup has to be perfect, the hair has to be perfect, but I work with a really incredible team of people who have worked with me on these other shows before, and I’m already working on the voice."
After recently wrapping up his final performance of a two-year, multi-city run stepping into the shoes of Stewart, Raftery spoke to THR about his process, his team and what it was like to run into Wintour out in the wild.
How do you choose who to build a show around?
Anna was the only one that kind of suggested herself to me. The rest of them I had to think about who I wanted to play next. I feel very strongly about playing alternate genders because as a writer, why should I write with one hand tied behind my back? I love the idea of writing for women, I love the idea of writing for men, and I love the idea of playing both of them. The shows are not all one-person shows. The Anna Wintour one has one other character who plays Grace Coddington. Originally it was André Leon Talley, but for the five-year anniversary that we’re performing in three weeks, I’ve changed out characters where now it’s Grace Coddington because of the success of that documentary The September Issue. Then the Andy Cohen show, the Housewives were obviously all characters, as was Anderson Cooper. Then Martha, her daughter was a character, Snoop Dogg was a character and there were ancillary characters. Calvin Klein was a three-person show [with] Donna Karan and Ralph Lauren as well. Ivanka is going to be just me, and Jared Kushner’s going to be played by a life-size cardboard cutout. It's eerily accurate.
What sparked your interest in acting?
When I was growing up, I certainly didn’t know anyone in show business, so I never knew that it was really a viable career choice. I thought I wanted to be a lawyer and I realized that everything about law that I was attracted was the performative aspect of it. I grew up loving that movie A Few Good Men, with Tom Cruise screaming in the courtroom. When I was in high school, I got a job interning at a law firm and I never saw the inside of a courtroom. I was always inside a copy room making copies or redacting contracts. Then as I got older, I realized I wanted to try and do it.
How do you prep for a character? What’s your process?
It depends on how well known the person’s voice and likeness is to the public. For instance, Anna Wintour, everybody knows exactly what she looks like, but many people do not know what she sounds like. She has kind of a quiet voice, so I made sure I looked like her and I created a voice for her. Calvin has kind of a scratchy voice and a Bronx accent. I grew up in Brooklyn, so I was able to do that. Martha I worked very, very hard on because everyone knows exactly what she looks like and sounds like, so I worked very hard to get her voice down. I’ll do the same for Ivanka. I’m already working on her voice, but it really starts with research. I read everything I can find, I watch a ton of interviews, just get their mannerisms down; it’s just a ground-up kind of thing, you just have to start at the bottom and work your way up.
Did you impersonate anyone as a kid?
I’ve always been kind of a good mimic. I used to like make people laugh in school by imitating teachers. I’m able to pick up on people’s ticks, which really makes a good mimic. Like when you watch someone do an impersonation of someone you go, “Oh, yeah. He does always do that. He does always lift up his right shoulder.” That kind of little stuff always jumped out to me and made me particularly good at it.
Could you tell us a little bit more about that team and how involved they are in your process?
Martha was the first time I had to dedicate a hair and makeup person with me every show. So, I have a director who’s directed all of my shows; his name is Jay Turton, and he and I have all of our script meetings together. He shepherds the writing process. It’s just good for me to have someone to bounce my ideas off of. When you work alone, it’s kind of working in a perfumery, like you can’t smell anything after a while, so you need to have someone else in the room to say, “Hey, does this make sense? Is this funny?” Then, once we get further down into it I have someone who does all the wigs and makeup. We’re shooting the poster for Ivanka Sept. 15, so I’ve used the same photographer for every single one of my posters and he’s wonderful; his name is Brendan Burke. I’ve used the same actors over and over, I mean, it’s really great. I’m very, very fortunate that I’ve been able to find these people who are just as dedicated as I am to the theater, because nobody’s getting rich.
Have you ever met anyone you’ve impersonated?
I’ve met all of them. I was Calvin Klein’s assistant for one day and quit. I recently met Martha in the lobby of a building and her assistant saw me first and gasped when she saw me because she had seen the show. And then Martha was kind of cool. I showed her a photo of me as her and she said, “Not bad.” Andy Cohen, I told you I was on his show as Anna Wintour. And then I ran into Anna about a year ago in an elevator and she had donated her sunglasses. The last time I did an Anna show, we did it as part of a charity auction for the Trevor Project that I initiated. I got an email from Vogue saying Anna wanted to donate a pair of her sunglasses to the auction. And the super cool thing about that is that two of my friends bid on them, bought them for me, so this is the first time, I think Sept. 4 will be the first show where I will be actually wearing her sunglasses.
Comedy is so different now. Some people tread lightly in terms of what they’re writing and the subject matter. How do you approach that?
This is a really bad time for comedians because people don’t have a sense of humor. People are lurking in the shadows desperate to be offended. It’s a really dangerous thing about our society right now, because we should be able to laugh at things without people taking them literally. That’s the reason why a lot of comedians don’t play colleges anymore, because people in college especially are the ones who are the most sensitive about things and the biggest ones to be offended. And sometimes when you look at something that’s so obviously a joke, sometimes people just want the attention of being offended.
What’s the hardest thing about these shows?
The hardest part is probably just the stamina that it takes to be onstage for 90 minutes by yourself. People always ask me, “Are you nervous? Do you ever get stage fright?” and I’m like, real life is terrifying. I opt to live onstage. I love nothing more than being onstage in front of people. So that question doesn’t really apply to me, and I know a lot of the theater people that I know feel the same way. Like, film and TV is great, and there’s obviously different things you can do with each medium. Film is a director’s medium, television is a writer’s medium — stage is the only true actor’s medium. Once they call "places," there’s no stopping, there’s nothing you can do. If you are onstage in a scene with someone, you have to learn to focus and how to hold focus. There’s no director there pointing the camera in your face where the audience is supposed to look. There’s so much excitement there. I literally have one rule as a performer: You can do anything you want to an audience except bore them, and that’s what I keep in my head when I’m writing.
This article was originally published by The Hollywood Reporter.