Some standup comedians would be distraught by a silent audience failing to fill the room with laughter, but not Tranna Wintour. She is unbothered and unmoved – that’s just comedy.
Times have changed within the comedy space. The kind of jokes riddled with isms and phobias that used to receive little to no backlash now become public discourse, viral fodder, and op-eds in prestigious publications. Comedians either feel like everybody’s too sensitive and argue comedy is meant to be boundaryless, or there are those committed to making comedy free from offending already marginalized groups. Household names like Dave Chapelle and Aziz Ansari have publicly struggled with the changes some lovers of comedy expect and despise cancel culture.
As for Wintour, she has experienced both the good and the ugly.
“As a trans feminine person doing standup comedy, there’s a particular struggle because I feel like when I’m performing in front of a largely straight, cisgender audience, I feel like the men in that audience tend to be kind of scared of me,” she says. “So there’s this automatic closing off that’s annoying and frustrating. I’m sort of figuring that out, but also, I don’t really care.”
With a strong sense of self and trust in her instincts, Wintour is more interested in building her own audience.
“I think when I first started out, there was an appeal or a sort of — an excitement in the challenge of conquering any audience,” she says. “But I’m really over that; I know my worth.”
Although the goal of all comedy is to make people laugh, Wintour also wants to make comedy that is nuanced and personal. Her two biggest influences are Margaret Cho and Sandra Bernhard, who she calls pioneers of the one-person show. “I really love things that go beyond the surface and that go really deep,” she says.
She has performed in a slew of festivals including Sled Island (Calgary), SheDot (Toronto), LadyFest, Pride Toronto, and Montreal Sketch Fest. In 2015, she performed her solo show, TRANTASY, in the Montreal Fringe Festival and a year later brought the show to New York City’s legendary Duplex Cabaret Theater. Wintour has been selected as a competitor in SiriusXM’s Top Comic three times and was a featured guest on Bernhard’s SXM show, Sandyland, which has hosted such luminaries as Bette Midler, Gloria Steinem, and Sarah Jessica Parker. She was one of Just For Laughs’ New Faces Canada (2019) and was named by Fashion magazine as one of the queens of Canadian comedy.
When she’s not on stage she is busy co-hosting and co-producing her podcast Chosen Family with her creative partner/comedy soulmate, Thomas Leblanc. In 2020 she released her debut album, Safe From Your Affection, which is a mix of original songs and covers. Her talents may be diverse, but comedy is still the foundation of everything that she does.
“The greatest joy is just being onstage and having that instantaneous live experience with an audience,” she says. “For me, nothing beats that.”
Find out more about Tranna Wintour at TrannaWintour.com and follow her on Instagram and Twitter – @TrannaWintour.