Gregory is an actor, director, and writer originally from Pictou, Nova Scotia.

After graduating from The National Theatre School of Canada in Montreal, Gregory moved to Toronto to direct Anita Majumdar’s Fish Eyes at SummerWorks. This production continued to develop and played at the Harbourfront Centre, Theatre Passe Muraille, toured across Canada and internationally to The Other Festival in Chennai, India.

Most recently, he wrote the book for and directed the Globe and Mail’s Critic’s Pick new musical De Profundis: Oscar Wilde in Jail at Soulpepper, which earned six Dora Award nominations (winning for Outstanding New Musical and Outstanding Performance), and a Toronto Theatre Critic’s Award for Best Direction of a Musical. His play Bremen Town, which premiered at the Next Stage Festival, earned another six Dora Award nominations including Outstanding Production, Outstanding Direction and Outstanding New Play.

Other directing work includes Punk Rock for The Howland Company which was listed in the Top 10 Theatre Productions of 2018 by Now Magazine and nominated for 2 Dora Awards; Hosanna – listed in the Top 10 Theatre Productions of 2016 by Now Magazine; The Heidi Chronicles; and the world premiere of Rose: A New Musical, for which he received the 2019 Dora Award for Best Direction. This production earned 11 nominations, winning 3, including Best New Musical.

As a collaborator Gregory has helped to create and perform Alligator Pie which was nominated for 3 Dora Awards. This show toured across the country and in 2017 the cast recording won the Gold Medal: Best Audio Book – Fiction from the International Radio Program Festival in Zurich, Switzerland. He also collaborated on (re)birth: ee cummings in song which was nominated for a Dora for Best New Musical. Both of these shows played in New York City at The Pershing Square Signature Center in 2017 as part of Soulpepper Theatre Company’s five-week residency.

As an actor, Gregory played Ron Weasley in the Toronto premiere of Harry Potter and the Cursed Child and spent 12 seasons as a member of Soulpepper Theatre’s acting company, performing in over 40 productions. He has also worked with Canadian Stage, Necessary Angel, Crow’s Theatre, Company Theatre, Tarragon Theatre, Young People’s Theatre, Small Wooden Shoe, Shakespeare in the Rough, The Classical Theatre Project, Centaur Theatre and The Canadian Opera Company. He is a series regular in the Crave TV comedy “Pillow Talk” (2 Canadian Screen Award nominations).

Gregory is passionate about artist training and mentorship. He has taught at Toronto Metropolitan University, University of Toronto, The National Theatre School, Neptune Theatre School, Soulpepper Academy, The 519, and in elementary, junior, and high schools across Toronto.

He has twice been listed in the Top Ten Theatre Artists of the Year by Now Magazine, nominated for eighteen Dora Mavor Moore Awards, and shortlisted for the Pauline McGibbon Award for Emerging Director. He is a graduate of Acadia University, the National Theatre School, and the Soulpepper Academy.

Photo by Dahlia Katz