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“My favorite moment during a show is always the big breakthrough,” says transgender stand-up comic Tranna Wintour. Described by legendary comedian Sandra Bernhard as “a candle in the window on a cold, dark winter’s night”, Wintour is a sensation in her hometown of Montreal, where audiences flock to see her perform at comedy clubs and comedy nights throughout the city. Her audiences are mostly made up of “cisgender” people – cisgender being a word to describe those who are not transgender.

“If at the beginning of my set they might be a little reluctant to laugh out loud or don’t know how to react, there often is a turning point when they allow themselves to be entertained by me, and it’s a really great feeling.”

That moment of comfort and acceptance is in some ways symbolic of the journey many transgender people are currently going through in mainstream culture and society. Caitlyn Jenner – who completed her transition with a 10-hour facial feminization surgery that included a brow lift and jawbone reshaping – has brought on a monumental shift in perceptions, leading to heightened knowledge and awareness of transgender issues, plastic surgery, and facial feminization procedures.

“I think the masses still have an old-school vision of what it means to transition,” Wintour explains. “Most people think trans people want to “pass” as the gender they identify with, and see Caitlyn’s transition as the golden standard. In fact, the option to fully transform is not available to every transgender person, and it’s not what every transgender person wants. Because Caitlyn Jenner is such an A-list star, there’s probably too much attention given to her transition, perhaps at the expense of other voices, but ultimately she has done a lot of good.”

tranna wintour

Wintour is also a vocal proponent of plastic surgery and glamour – as long as it speaks to one’s higher truth – and appreciates that facial feminization surgery can help people in a society that pressures transgender women to pass. However, she doesn’t feel that the media coverage of Jenner’s procedures has caused members of the transgender community to further question their own appearance.

“Jenner has definitely opened up the discussion,” she says. “There were a lot of things I didn’t know about the different surgeries that she had. I think it’s pretty amazing that we are living in a time where science has become so advanced that these procedures can exist. It allows those who are transitioning in a more conventional way to appear on the outside the same way they feel on the inside. I’m all for individual freedom and for everyone doing whatever they feel is necessary to look the way they want and feel the way they want. While I personally find that there is something to be said about working with what you have been given naturally – the beauties I look up to and am inspired by are unconventional beauties and faces that have character – I’m all for plastic surgery. I’m all for people creating their own beauty on their own terms.”

Dr. Harrison Lee and Dr. Gary Alter explain Jenner’s 10-hour facial feminization procedure.

“Cisgender people are preoccupied with transgender people passing, but from what I see within the trans community, passing has become much less important. I think it’s because people are more comfortable in general when they are able to label somebody, so a cisgender person has a much easier time with a transgender person passing as their identified gender. It’s just easier for them to understand. I think the most important thing to relate to cis people is there is no one way of being transgender.”

Wintour shares this positive message of love and hope with her audiences whenever she headlines comedy clubs or counsels readers in her advice column:

Every day I am more and more the person I want to be, and I feel I have things to share with people. Even as a performer, I feel my job is to encourage people to live the best version of themselves that they can be, to live out loud and not be ashamed. Live authentically and be honest with yourself.

For more Tranna Wintour and her upcoming comedy shows, visit her official Facebook page, personal website, Twitter feed and #AskTranna advice column.

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About The Author

Articles by

Richard Burnett is a columnist and blogger for the daily Montreal Gazette.