MTL Blog had the opportunity to speak with Wintour ahead of her Just For Laughs and Zoofest shows, which include a free performance on July 22. The conversation only confirmed what I already suspected: that Wintour is funny, charismatic but most of all down-to-earth, your favourite trans person's favourite trans person. (If your favourite trans person isn't me, your mileage may vary there, but so does your taste, apparently.)
From her early love of Madonna to her favourite Montreal metro station, Wintour gave considered answers to my silly questions, granting us a closer look at this rising star in Canadian comedy and performance from a uniquely Montreal perspective.
MTL Blog: When you're travelling, what are three must-haves you pack in your suitcase?
Tranna Wintour: Well, I need a book. I can't travel without a book. Even though very often I don't end up reading the book that I bring. But I always think in my mind that like, "I'm going to read this whole book." It's essential to me.
I travel with so much crap, and it all feels very essential. I'm not a light packer.
I need my headphones because I do listen to a lot of music while I'm travelling, whether I'm on a bus or a train or just waiting in an airport. I feel like listening to music or a podcast really helps pass the time. So that's super essential to me. One time I forgot my headphones and it was a nightmare.
And I really need all of my skincare stuff. Like, I need my moisturizer and my cleanser and my serums. I cannot travel without my beauty products.
What's your favourite underrated Montreal spot to bring your friends?
I would bring my friends to the Wiggle Room, which is an amazing burlesque bar and club [where] I've performed many, many times, and I just think it's such a magical space.
I don't know if I can fully call it underrated, but I feel like there are still many who don't know about it.
What's one thing you think Montreal does better than any other city?
I think Montreal knows how to chill. I feel like so many big cities are so work-centric, and I do see that becoming the case for Montreal. I find that very alarming because, to me, I think it's so important that Montreal remains a city that understands leisure.
And I think Montreal also does... I don't know if "trash" is the right word. But I feel like Montreal does punk better than most big cities, especially these days where. again, I feel like so many big cities have just become so corporate.
I feel like for so long, Montreal has really held on to its punk spirit. Again, I see that dissipating a little bit, which I find very alarming. But there's something about the punk spirit and just, like, being able to chill that I feel go hand in hand. And I really don't want Montreal to lose that because it is something that very few cities have left.
How often do you get recognized when you're out in the world?
It literally happened to me two days ago, I got recognized on the metro. Someone saw me and wanted to take a selfie, which was super sweet, and they were like, "You're the first celebrity I've ever met!" and I thought it was so cute and sweet. Everyone is always so nice!
I'm such a fan girl if I happen to run into an artist or someone that I really like. It's kind of surreal to be on the other side of it.
Kathy Griffin used to have a show called "My Life on the D-List" which was sort of about all the indignities that she had to suffer as someone who's kind of famous, but kind of not working in this industry.
I just relate to that so much, because I'm on the metro every day, you know what I mean? My life isn't really that glamorous. And so often I get recognized when I'm, like, at the grocery store.
One time, this winter, I got recognized at the pharmacy when I was really, really sick and had to go get medication and was feeling so gross. But again, everyone is so nice, and I think all performers need validation every now and then, at least just to feel like our work is resonating because it's such a hustle all the time.
It's so much work and we give so much of ourselves to what we do. Sometimes it can almost feel like you're just in a little bubble, you know? But when you have these moments where someone comes up to you and they're like, "What you do and who you are means so much to me," it always gives me such a boost and makes me feel like, okay, what I'm doing is at least resonating with one person, so it's worth it.
As someone who rides the metro every day, what's your favourite station?
I like the metro stations that are the closest to above-ground as possible, the metro stations where you can see a little bit of sunlight. My metro station is Jolicoeur, and you can see the sunlight when you're on the platform.
I love all the ones that have the stained glass. Vendome is a good one, too. The ones where you're literally like 10 flights of stairs down are probably my least favourite.
What is the funniest thing that has ever happened to you while performing?
I was doing this French show called Le Show Queer, which has an all-queer lineup of comedians. And when I started my set, I asked the audience if there were any straight people there, and no one responded.
And so there was this collective moment of all of us laughing and then just sort of like running with that, and telling the audience that we really need to treasure these moments because they happen so infrequently, to be in a space with no straight people.
Not that I don't love straight people. I'm sure if you write that you're gonna have people being all "straight pride," you know, like, people take things so literally, but that was a funny moment. The moments that become sort of improvisational to me are always the most magical.
In the next year, what's one big goal you have that you're really excited about?
My big project for next year is to do my first tour. So touring Quebec, touring Canada with a one-woman show, I've started putting that together with my team. It's been a lifelong dream for me.
I grew up being the biggest Madonna fan, and watching her documentary "Truth or Dare" just always gave me this fantasy of what it would be like to be on the road and touring, going to different cities and seeing different audiences. So fingers crossed, that will be happening next year, and it really has been a lifelong dream.
