Tranna Wintour is a performance animal

Bilingual stand up comedian, singer song writer, podcast host; Tranna Wintour is a powerhouse entertainer in Canada. I spoke with Just For Laugh’s New Faces Canada alum and host of CBC’s Chosen Family to discuss her stand up career, her music, and the transition into French comedy.

Tranna Wintour. Photo by Maxyme G. Delisle

How did you get your start in stand up?

Early in my life, I realized I had this performance animal I didn't know how to express. Growing up being bullied, I didn't really have any coping strategies or information on how to deal. I wanted to be as invisible as possible, which was so in conflict with my showgirl nature. It took years to understand who I was and come to a better understanding of my Transness. Those realizations about myself coincided with me finding stand up comedy through watching Sandra Bernhard and Margaret Cho. As soon as I saw it, I knew stand up was the thing I needed to do. There was a lot riding on that first open mic for me, because I already knew that this is it for me.

Didn't that first open-mic go well?

It did, and it remains in the top three most terrifying moments of my life. I was physically shaking the whole day. It was at the Comedy Works — which no longer exists — where you had to call in and leave a message on their answering machine requesting a spot. Making that call was terrifying, and there was a part of me praying they wouldn’t call back, but they did. It was also May 20, which happens to be Cher’s birthday. I saw people on social media posting about it and remember thinking it's a good sign that this moment is happening on Cher's birthday. I didn't plan it, but there was something comforting about it.

What goes into crafting your brand?

I swear, it's really not that calculated. It goes back to that performance animal I was talking about, and I just love making people laugh. For me, the best thing about performing is about creating a feeling of connection. Authenticity and transparency have always been important to me, and I never try to create a false image to make anything look better than what it is.

You started doing stand up in French, how's that been going?

I mean, it all shut down while I was starting, but it was going well up till that point. It was something I’ve wanted to do for a while, because I'm committed to being in Montreal. If I'm going to stay here, I have to get in on the French side because there's a lot more money and opportunities. It was terrifying because, even though I'm bilingual, I never speak French socially, only at work, so my French is very academic/business. I can't rely on those same improvisational moments I have in English, so I write sets out word for word and memorize that. But again, things aligned, and I was seen by the right people at the right time. French comedian and actress Virginie Fortin saw me at an open mic, loved what I was doing, and booked me for this TV show that she used to host. In contrast, I’ve been doing stand up in English for eight years and I still have never got a televised set. I was amazed it moved that quickly. 

I get where you're coming from. I feel like a lot of Anglo comedians don't understand how huge French comedy is.

It's massive. And it feeds directly into their television industry, which is a bit scary. I felt like such a fish out of water that first French TV set. I'm grateful that I threw myself in the deep end. Often, I need to be in those sink or swim moments because otherwise I'm too much of a procrastinator. A lot of good comes out of high-pressured situations because there's the part of me that will not allow myself to fail. Maybe it's the performance animal, she just comes through.

You came out with an album, Safe From Your Affection, during quarantine. How was the pivot to music?

You know, the fantasy was always that I would be a pop star. But I don't play instruments, and I can't compose music, and I didn't know if my voice was any good. It wasn't even a dream; it was a fantasy of something that you would never happen. Then I met an extremely accomplished musician Mark Andrew Hamilton through performing stand up and he wanted to start working together. At first, we were like putting cover songs together and started recording them, but then it snowballed into us doing a full album. A lot of the plans were scrapped because of COVID. When things hopefully get back up and running, I'll find a way to incorporate it into things. Out of everything I've done, it’s the thing that I'm proudest of. 

You and Thomas Leblanc (CBC’s Chosen Family co-host) have developed quite a partnership, how has that evolved? 

I first met Thomas because he came to one of my shows, and then a couple of months later, ran into him at a mutual friends Christmas party where he asked questions about starting stand up. From there turned into a social media friendship. Famously, he’s a Celine Dione fan and I am not, and when Celine’s husband passed, his funeral was open to the public. Literally any random person could line up at the church, go in and give their condolences to Celine herself. It was insane, I needed to go! I asked him to come with me, but we got there too late and they had closed the line. So we just went to like Starbucks and it was the first time we hung out one-on-one. He told me about this idea which became our first cabaret show together, Sainte Celine: A Dion Cabaret, which was a success. We expanded into other projects and he’s become an essential part of my creative and personal life. He’s one of my best friends, and I just love working with him. We also complement each other so well. Thomas is an amazing hustler and so unafraid to go for things, and as I said, I hate asking for things. Thomas always wants to push things further with us and pushes me to do better. Finding that person who does that for you doesn’t happen often, and I’m grateful for it happened for me.

What’s the best piece of advice you have?

Allow space for all your creative impulses and diversify your skills. Looking at this year, I’m grateful that I did diversify my career and got into writing. If I had kept things strictly performance, I would have been royally screwed. It’s important to keep an open mind to things that come your way. Don't try to rigidly define what you want. Also, get a lawyer. It’s expensive, but so worth it.

Follow Tranna at www.trannawintour.com