Tranna Wintour is living the trantasy

An expanded interview with the Montreal entertainer about her Trantasy show, her fashion muses, dreams of Anna Wintour and the strength of her female spirit.

Tranna Wintour inside pic (640x446)
Tranna Wintour
If you haven’t had the pleasure of seeing Tranna Wintour on stage, her name might ring a bell anyway, and not because you’re confusing her with her namesake, Vogue editor Anna Wintour. Tranna, the only transgendered stand-up act in town (and one of only a handful on the East Coast), is on the cover of the June edition of our newspaper (where a shorter version of this article appears) and she was all over last month’s Best of MTL readers poll, making the Top 5 in Best Comedian (#3), Best-Dressed Montrealer (#4) and Best Instagram (#1).

She’s been performing her stand-up/musical/cabaret shows around town and beyond since debuting at a ComedyWorks open mic in 2013, and this month she’s starring in a one-woman show, Trantasy, as part of the Fringe Festival.

Tranna Wintour: Basically the show is the culmination of everything that I’ve been working on over the past few years. I’m bringing together all of my strongest material and of course throwing in some new stuff, with entirely new musical numbers. All the material that I’ve gathered for this show, I’m contextualizing under a loose theme of fantasy. I think the things we hide and relegate to our fantasy world are often the truest things about ourselves.

CULT-Vol3No9-cover (525x640)Lorraine Carpenter: Do you have a sense of who your audience is, in terms of gender and sexuality?
TW: The majority seem to be straight females, which, for all intents and purposes, is what I am — I don’t really identify as heterosexual, but I do identify as a woman who’s exclusively attracted to men, and my material is very pro-female, so straight women relate to that. But I’m really happy to say that I’ve performed in front of so many different groups, the whole range, and fortunately most audiences respond really well. There was a good year and a half of of getting my act together between when I decided to do comedy and when I actually got up and did my first open mic, and I was really fearful that there would be animosity and that I’d be really misunderstood. I was ready for a fight, basically, but I was so embraced by my fellow comedians and by my audience, and that was an amazing thing that took me by surprise in the best way possible. I don’t really identify with any particular label — I’m just me, and when you know who you are and you’re confident, people respond to that. I think that’s why it’s largely gone so well.

LC: One of the many Best of MTL categories you appeared in was Best Dressed Montrealer, and wardrobe is obviously an important element of your act. So I’m wondering, who are your fashion muses?
TW: Fashion obviously is so important for me and it’s something that I just absolutely love — I love that challenge and that opportunity to express myself visually through fashion. My fashion influences come from everywhere but definitely strong females with a strong, iconic sense of style. There’s this really great cult icon, Amanda Lear, who’s amazing. She was really big in the ’70s, she had this great disco aesthetic, and disco’s definitely a big inspiration for me, the time period from 1977 to 1981.

Kylie Minogue is a really big one — if I’m ever hesitant, “Should I buy something? Should I not?”, I think “Would Kylie buy it?” and I can trust in that. Paris Vogue is definitely a big inspiration especially in the years it was edited by this woman named Carine Roitfeld who had this very twisted sense of style. She would just mix really crazy things and there was a strong sexuality and subversiveness to her work that I really respond to.

LC: This might be verging on trans-101 territory, but I’ve heard you say that you’re in boy mode most of the time, and I was wondering how that works.
TW: I make that distinction for people, but for me it doesn’t matter what I’m wearing or what I look like — whether I’m wearing a dress or a pair of jeans or make-up and a wig or no make-up and no wig, I’m always the same person: I’m always female. That’s my spirit and my spirit exists independently of all of that surface, but it’s hard for people to understand that.

For the people who do have a concept of what transgender is, it’s usually the very basic definition of feeling like you’re the wrong gender. But there’s no one way of being transgender. People expect that someone who’s born genetically male but wants to be female is living their whole life visually as a female, but for me, I’m not on hormones, and when I’m not wearing make-up, I don’t feel like wearing a dress. If I’m just going to the grocery store or going to my day job, I’m just gonna throw on jeans and a tshirt, no make-up or wig, but that doesn’t make me a boy on technical level. Most of the time I look like a boy, but the truest part of who I am is female, 100 per cent. There’s no question about it. I don’t really have the sensation of being in the wrong body because I feel so strongly connected to my female spirit that the exterior really doesn’t matter. I prefer to express myself visually as female, but it’s not what counts.

LC: So you’ve noted that you’re not a drag act, and that “Tranna Wintour” is not a character per se, but it’s been your stage name and go-to look since 2008 — how do you feel about Anna Wintour now?
TW: I’ve always been drawn to her as a character. Whether intentionally or not, she’s cultivated this persona as a woman who’s feared, and I’m so drawn to that. I’m always drawn to powerful women, but there’s a quietness about her — most of the other women that I look up to are performers and they’re very in your face, but Anna’s power is a lot more quiet and she’s much more mysterious, and that makes her all the more scary.

My biggest fantasy is to be face to face with her, even just for two minutes. It’s definitely a moment that I dream about. Just last week I had this very vivid dream that I was taking over her position at Vogue and she was showing me around the office, which was this giant mall. Then I woke up and realized it wasn’t real, and I was so disappointed. ■
See Tranna Wintour’s Trantasy continues as part of the Fringe Festival at the Wiggle Room (3874 St-Laurent) on June 16, 18–21, 9 p.m., $12