Novelist, poet, filmmaker, director, actor, and drag queen extraordinaire…. Sky Gilbert is one of Canada’s most controversial artistic forces. He was the co-founder and Artistic Director of Buddies in Bad Times Theatre in Toronto, Ontario, Canada, for 18 years. In 1997 Sky Gilbert left Buddies to have more time for creative pursuits and to start a second career as a scholar and Professor at the University of Guelph, were he was a University Research Chair in Creative Writing and theatre.

Recently Sky left Guelph (after 23 years teaching) and is now a Professor Emeritus — which means he is able to explore all of his artistic dreams as filmmaker, playwright, novelist, poet, performer, and Shakespeare scholar. Sky is always working on plays, novels and films, and Dr. Gilbert is also presently working on his third book about Shakespeare, tentatively titled Shakespeare’s Effeminacy.

Since 2018 Dr. Gilbert has published several books: a novel I, Gloria Grahame (nominated for a ReLit Award), a book of essays — Small Things (which received the non Fiction prize at the Hamilton Literary Awards) and two books of cultural criticism centred Shakespeare’s work — Shakespeare Lied and Shakespeare Beyond Science: When Poetry Was the World (both, Guernica). Sky’s play about his parents Pat and Skee was produced by Theatre Aquarius in 2022 to critical acclaim.

After leaving Buddies in 1997 (and up until 2018) Dr. Gilbert wrote and produced several plays in Toronto with his own Cabaret Company (most of them at Buddies) including the Dora Award winning Will the Real J.T. LeRoy Please Stand Up?, Bad Acting Teachers, A Few Brittle Leaves and The Situationists — which won the ‘best original play’ Dora in 2011. He also founded a theatre company in Hamilton, Ontario called Hammertheatre, which began producing plays in 2007, staring with Crack. Hammertheatre hits included Hamilton Bus Stop, Toller, and Naked Hamilton (which traveled to the New York Fringe in 2015.) His play about a boy who ‘comes out’ on a farm St. Francis of Millbrook was produced in 2013 by 4th Line Theatre. During this period Sky wrote and published several novels and books of poetry and a work of non—fiction, including the ReLit award winning An English Gentleman in 2004 with Cormorant.

From 1979 to 1997 At Buddies, Mr. Gilbert wrote and directed his own hit plays: inducing Drag Queens on Trial, Drag Queens in Outer Space, The Dressing Gown, Playmurder, Ban this Show Pasolini/Pelosi, Capote at Yaddo. Drag Queens in Outer Space had a triumphal run at Theatre Rhinoceros in San Francisco in 1989. In 1996 Buddies toured Sky Gilbert’s play Ten Ruminations on an Elegy Written by William Shakespeare. to London England’s Riverside Studios. Sky received the Dora Award or playwrighting for his play The Whore’s Revenge. Dr. Gilbert’s plays have been produced in New York City (at ‘The Glines’), Chicago (at Bailiwick Theatre), San Francisco, Houston, Phoenix, Vancouver, and Montreal. During this period Sky also made four films, his third feature length film My Summer Vacation was released on video in 1999 by Waterbearer Films..

As a theatre director of other’s work, Dr. Gilbert’s list of credits is also extensive. For the Shaw Festival (in Niagara-On-The-Lake, Ontario) Dr. Gilbert directed Anything Goes, and Wilde’s Salome and was the assistant director for the original Shaw Festival production of Cyrano de Bergerac. Other critically acclaimed productions directed by Sky Gilbert include: Treatment for Another Stage, How I Wonder What You Are for Theatre Direct and The Lindros Trial for Twinkle Twinkle Theatre.

Dr. Gilbert has a PH.D from the University of Toronto, and Sky has received many prestigious awards, including Pauline McGibbon Award for directing in 1985, the Dora Award for the production of his play SUZIE GOO: PRIVATE SECRETARY in 1992, The Margo Bindhardt Award, and The Silver Ticket Award. There is a street in Toronto named after him ‘Sky Gilbert Lane.’