Gregory is an actor, director, and writer from Pictou, Nova Scotia. A graduate of The National Theatre School of Canada, he began his career in Toronto directing Anita Majumdar’s Fish Eyes at SummerWorks, later presented at Harbourfront Centre, Theatre Passe Muraille, and internationally at The Other Festival in Chennai, India.

He wrote and directed De Profundis: Oscar Wilde in Jail at Soulpepper, which earned six Dora nominations and won for Outstanding New Musical and Outstanding Performance, along with a Toronto Theatre Critic’s Award for Best Direction. His play Bremen Town premiered at the Next Stage Festival, received six Dora nominations including Outstanding Production, Direction, and New Play, and played at Tarragon Theatre in the fall of 2025.

Other directing credits include Punk Rock (The Howland Company), Hosanna, The Heidi Chronicles, and Rose: A New Musical (Soulpepper), for which he won the 2019 Dora Award for Best Direction. Rose received 11 nominations and won three, including Best New Musical.

As a creator, Gregory co-devised Alligator Pie and re(birth): ee cummings in song, both performed in New York during Soulpepper’s 2017 residency. Alligator Pie toured nationally and won the Gold Medal for Best Audio Book – Fiction at the International Radio Program Festival in Zurich.

As an actor, Gregory portrayed Ron Weasley in Harry Potter and the Cursed Child and spent 12 seasons with Soulpepper Theatre, performing in over 40 productions. His credits include work with Canadian Stage, Crow’s Theatre, Tarragon Theatre, and others. He is also a series regular on Crave TV’s Pillow Talk, nominated for two Canadian Screen Awards.

He has taught at Toronto Metropolitan University, the University of Toronto, the National Theatre School, and the Soulpepper Academy. A two-time honouree on Now Magazine’s Top Ten Theatre Artists list, Gregory has received 18 Dora Award nominations and was 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