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Sky Gilbert
Sky Gilbert. Photo by George Whiteside

Star Turns: Sky Gilbert

"I'm always going to have that bent to read and write and learn new things"

We meet at a restaurant near Robarts Library, where Sky Gilbert (MA 2000) is doing research. The gay activist/actor/director/drag queen/playwright/poet/writer who’s known for his raunchiness has reincarnated himself yet again, this time as an academic. Currently a teaching assistant for first-year English classes at U of T at Scarborough, Gilbert is studying for his PhD. His thesis is on Noel Coward as the creator of the modern construction of the homosexual male and theatre in the early 20th century.

But don’t imagine “one of Canada’s most controversial artistic forces” – as his Web site immodestly describes him – wearing the stereotypical tweedy jacket of an academic. The flamboyant co-founder and former artistic director of Toronto’s Buddies in Bad Times, the world’s largest gay theatre, is wearing fire-engine-red pants topped by a bright yellow poncho. He makes a bold visual statement but shakes hands surprisingly tentatively.

Gilbert is now the artistic director and producer of The Cabaret, a company that produces his works (The Birth of Casper G. Schmidt, The Emotionalists, Schubert Lied). He claims to be seeking more of a private life these days and enjoying the relative anonymity of the classroom, although his provocative web site ( gives an entirely different picture, including one of Jane, his female drag persona. This past July, Jane was filmed on Yonge Street talking with World Youth Day pilgrims and confronting religious hypocrisy and homophobia, two of Gilbert’s favourite targets.

But one on one, Gilbert is far from confrontational; in fact, he has an odd habit of closing his eyes while he’s talking, and doesn’t often make eye contact. When asked if he had to pick one persona that fits best, Gilbert says it would be the writer’s. “I think I always knew that but I didn’t want to be presumptuous,” he says. The publication of his first novel, Guilty (Insomniac Press, 1998) – an extremely scatological but funny, fast-paced monologue by a gay guy – solidified his authorial claim.

He’s currently writing a book, tentatively called Neverland, about a key relationship in the life of Peter Pan’s creator, James Barrie, someone he feels is a “kindred spirit to my aesthetic.” In 1910, the wealthy Barrie became guardian to five brothers, and exchanged daily letters with the fourth boy, Michael, for years. In 1921, at the age of 20, Michael drowned, and the almost 2,000 letters were later destroyed. The challenge that Gilbert has set himself is to imagine the contents of those lost letters.

In the meantime, Gilbert turned 50 in December. He ignored his arthritis, threw a party and dressed in drag to celebrate. He prefers not to dwell on the aging process, declaring that “It’s not necessary to be an old person.” Hmmm. Sounds a bit like Peter Pan.

It’s not clear whether Gilbert will still be wearing the academic persona when he turns 60, but one thing is sure: “I’m always going to have that bent to read and write and learn new things,” he says. Keep your eyes and ears open for the next persona.

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