Montreal's Own Tranna Wintour Gives the People What They Want: More Answers!

Have you ever just met someone and just knew that you were supposed to meet? What about connected so quickly that you schedule a dinner date immediately following an interview? Tranna Wintour is everything as advertised and more. She is a beautiful soul and someone who is so easy to talk to, the hours just melt away (literally we had dinner at 8:30 and sat until midnight talking). We asked She's Not Doing So Well podcast listeners if they had any additional questions and here is what she had to say.

What was it like to be around Bobby and Jim? 

Honestly, I fell in love with them (and Bobby's partner, Michael)! They are three of the nicest, funniest, most sincere guys I've met. I loved them so much, I literally invited myself to have dinner with them the next night, which I never do!  

I'd like to hear her talk more about how straight people can be supportive to trans people. I don't personally have any trans friends so it would be helpful for me to hear more of her perspective on that from a trans person?

That's a great question! It's always a bit of a tough question for me to answer because it ultimately just comes down to common decency and respect, which should be extended to EVERYONE. Just by you asking this question, I can assume that you are a kind, open person but maybe not everyone around you is. A Great way for straight people to help trans people is to talk to their straight friends. If a friend says something transphobic, or treats a trans person badly, talk to your friend! Help your friends become as kind as you are. Also, a lot of trans people work independently, so if you know of any trans artists in your city, support their work (go to their shows, buy their music, or whatever they're selling)! That's a great way to support trans people. Read books by trans writers. Two books I would suggest are "I'm Scared of Men" by Vivek Shraya and "I Hope We Choose Love" by Kai Cheng Thom. 

Do you think there will be a day where you won’t have to explain that you are a trans woman?

Yes! But I don't know if I'll see that day in my life time. I do imagine that one day gender will be completely irrelevant and the binary of male/female will be abolished. 

Who would you have dinner with dead or alive? 

Dead: Dalida (she is a legendary french artist who killed herself in 1987. She is one of my favorite performers/singers and I would LOVE to have dinner with her). Alive: Jennifer Lopez (lol). 

I noticed in pictures on the shes not doing so well Instagram that the picture you took with Bobby you did not have any makeup on or a wig. Do you try to stay incognito while in your home city?

Nope, it's not about staying incognito, although I do like being incognito (which I am all the time, I'm not famous lol). When I'm navigating my everyday life, I don't wear makeup or a wig, because it's just too time consuming and I already spend so much time on my appearance as a performer. But whether I'm wearing makeup or not, I'm still very much a trans woman, and I think that's hard for people to understand. I wrote an essay for The Walrus about the impossible beauty standard for trans women that I'm really proud of it, you should read it if you have the chance, it will fully answer your question:

When are you going to come to Europe?

Omg it is seriously my DREAM to perform in Europe. I think I would do especially well in London and Paris. Do you have a hookup, producer friends, etc. Can you get me to Europe?! I really hope it happens one day.  

Go to comfort food?

Burger and fries. There is honestly nothing I love more than a juicy BURGER! 

What are you currently listening to? 

At this very moment I'm listening to Whitney Houston (I just watched the Netflix documentary last night and it is amazing and devastating). I have to admit I don't really listen to a lot of new music. I'm very attached to my divas: Madonna, Kylie Minogue, Cher, Mylene Farmer, Barbra Streisand, Mariah Carey, Diana Ross--those are the artists I listen to the most. And Alanis Morissette, who is my spiritual sister. 

What makes your heart feel full?

Performing when the audience is so with you and there is an electric connection, it is the most heart-bursting feeling for me. My heart feels full when I am around the people I love. It's corny but true. I feel so safe and loved around my people. Good conversation also makes my heart feel full. Laughing until you can't breathe makes my heart feel full. And hanging out with my baby niece! 

Is Justin Trudeau hot, creepy or creepy hot? or just trying too hard (brown face, trip to India)?

HAHA. There is something a little creepy about him for sure, and I've never found him hot, personally. He is way too bland for me sexually lol, but I am so fucking happy he won the recent election. I know a lot of people don't like him and don't feel like he's doing enough, and of course the awful blackface, and in a utopia, he would not be someone we'd choose, but in this moment in time, when fascism and conservatism are on the rise globally, given the context of REALITY, I feel very lucky to have him as prime minister. 

What could a young person trying to become a comedian do to make a career out of it?

I feel like I should be asking this question, I'm doing it and I still don't know lol It is so hard to make a career in the arts, and there is no step by step guide--which is part of what makes it so hard! I think the best approach is to focus on your creative work: write and perform as much as you can. Trust in what you're doing, stay committed. But there's also the business side: have a website, be find-able, be on social media, get your work out there however you can, maximize all the resources you can. I wish I could be more helpful! I will say, you will really be amazed by what can happen organically, when you focus on the work and let the work speak for itself. At the end of the day, the work is the only thing you can control. 

what is advice you would give someone trying to find their place in the world?

My advice would be, stop trying! I think when we ask ourselves "what is my place in the world" we are trying to find something, or an identity, to validate and justify our existence. But we don't need anything to justify our existence; our purpose is to simply be. Most of us have fallen into the capitalist trap of trying to prove ourselves, when we have nothing to prove. We are enough. We are always enough, even if we are not well-known, even if we are alone, even if we don't have a great job. Read A New Earth by Eckhart Tolle (and don't be dismayed by the flowery intro, you can skip the intro!) 

For more information on Tranna Wintour go to

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