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Alum successfully transitions — to comedy

Trailblazing trans comic Tranna Wintour takes stand-up world by storm
August 8, 2016
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By Richard Burnett

When transgender stand-up comic Tranna Wintour, BA 10, wowed her opening-night audience for her one-woman show I Am No Man at Montreal’s Café l’Artère in May 2014, everybody knew they had witnessed something special.

Tranna Wintour Tranna Wintour, BA 10 | All photos courtesy Tranna Wintour

Later that year in New York City, comedy legend Sandra Bernhard knew it too when she met Wintour. Today, fresh from her sold-out show Sainte Céline: A Dion Cabaret at the 2016 OFF-JFL festival, Wintour performs in comedy nightclubs full-time, and is a sometimes advice columnist.

“There is nothing more important than authenticity,” says Wintour. “To me, love, happiness, authenticity are all the same thing, and everything real and worthwhile in life springs from that.”

The fast-rising comedy star candidly opens up about her out-of-the-ordinary career and life path.

How did you come out as a trans woman at age 16?

Tranna Wintour: “For many years I falsely identified myself as a gay man, but that’s because, growing up, gay men were my only point of reference. When I was a teenager, there wasn’t any mainstream discussion about being transgender. When I did understand that I am transgender, I didn’t feel the need to come out. I just started to live my life authentically and unapologetically.”

How did you come up with your name Tranna Wintour?

TW: “A few years ago I dressed up as my spirit animal, Anna Wintour, and baptized myself ‘Tranna Wintour’ that night. Anna is, of course, the editor-in-chief of Vogue magazine. As much as I am fascinated by her, she represents corporate conformity, wealth and exclusivity.

I represent the opposite. My name subverts everything the real Anna stands for. What started as a kind of joke became my stage name, and it’s become the name that I go by in my everyday life. My closest friends call me Tranna or T.”

Sandra Bernhard has been very supportive of you.

TW: “Sandra has been a monumental inspiration and role model to me. We struck up a rapport on Twitter years ago, and after a year of corresponding through Twitter, I went down to see her perform in New York City.

Tranna Wintour with Sandra Bernhard Tranna Wintour with Sandra Bernhard

I got the chance to meet her and we had an instant connection. Every year since then our friendship has grown. She recently invited me to be a guest on her truly wonderful SiriusXM show, Sandyland, and she came to see my one-woman show at the Duplex in New York City.

She was the first one to give me a standing ovation at the end of the show and it made me cry. It’s not often a person gets to be supported by their hero, and it’s the most beautiful and overwhelming thing. I can’t say enough about Sandra and her generosity.”

Another of your celebrity supporters is legendary 1970s disco diva France Joli.

TW: “France Joli is one of the most beautiful people I have ever met. We have great chemistry, and she is so loving. She recently gave me a few vintage dresses from her archives, and when I wear them onstage I feel like I am carrying a piece of disco history, which is the biggest honour and thrill. I always have to pinch myself when I think of how supported I am by my heroes.

That’s where the importance of authenticity comes in to play: people know when you’re coming from the heart, they can see it.”

Is it true that Madonna blocked you from her Instagram account?

TW: “Madonna had posted a picture of a guy at a protest holding up a sign that said, ‘WHEN WILL YOU F*CKERS LEARN?’ I love Madonna, but it’s complicated. I hate how preachy and condescending she is and, for someone who calls herself a ‘rebel heart’ and a ‘freedom fighter,’ I don’t think she’s actually doing all that much to make the world a better place, especially considering her resources.

Tranna Wintour performs live Tranna Wintour performs live

So I commented on that Instagram post and wrote: ‘Madonna, when the f*ck will you learn?’ And I was immediately blocked. I wear it as a badge of honour, because it means Madonna saw it. And I can guarantee you she’s the one operating her own Instagram account because it is a mess.”

Why are fashion and glamour essential?

TW: “I love the Yohji Yamamoto quote ‘Choosing an outfit is choosing a life.’ It may be a bit extreme, but I think the essence of it is very true. How you dress is a reflection of how you’re living your life. Glamour for me is an expression of love. But I don’t think fashion is necessarily essential, it just happens to be something I really enjoy.

I think the negative side of fashion is that it can be extremely superficial and exclusionary. It is something that can be used to enforce divisions. When people use clothes to show off, or to act superior to someone else, is when fashion becomes very boring.”

Who is a fashion trainwreck?

TW: “Celine Dion is proof that money can buy expensive clothes but it cannot buy style.”

Why do you love Cher?

TW: “Because Cher is the only diva who’s real. She lets it all hang out, doesn’t try to hide her flaws. She makes mistakes and owns up to them. She doesn’t take herself seriously at all. She’s engaged and cares about the state of the world. And she’s gorgeous and stylish, and I could actually spend hours just looking at pictures of her.”

What is your dream?

TW: “My dream is to make enough money from my work as a performer to support myself without needing a day job. I am confident that my dream will come true, but it’s up to me to make it happen.

Nothing has been handed to me and I don’t expect anything to ever be handed to me. My dream isn’t even all that outrageous. I want to entertain and make people happy, and encourage people to break the mold and live the life they want.

I also live by the words of Dolly Parton: ‘Don’t get so busy making a living that you forget to make a life.’”

Now that you’re local comedy’s new “It” girl, are hot boys throwing themselves at your feet?

TW: “That is too funny, I wish they were! I’m a hot girl, because I say I’m a hot girl. I don’t need the attention of boys to validate that. Unfortunately we still live in a time where most people, men especially, are very rigid in the ways they’ve defined their gender and sexuality.

Even though straight guys are very often attracted to trans women, they see their attraction to them, on some level, as a threat to their heterosexual masculinity. I think what we need to see is an A-list, cis male celebrity openly date a trans woman. Then maybe men won’t be so scared of what other people think.

In the meantime, I don’t have time to deal with fragile masculinity.”

How did your studies at Concordia help shape your career?

TW: “I majored in creative writing and did my minor in professional writing, and the greatest thing I learned in those programs was how to self-edit; how, as much as possible, to look at your own work objectively. It’s not an easy thing to do, but it is vital. And those lessons carry over into everyday life. It’s important to be self-aware, to be able to see your flaws, to understand your limitations, to evaluate the decisions you’ve made and, ultimately, to take responsibility for all of it.”

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