Gregory is an actor, director, and writer born and raised in Pictou, Nova Scotia. After graduating from The National Theatre School of Canada in Montreal, he relocated to Toronto, where he directed Anita Majumdar’s Fish Eyes at SummerWorks. The production went on to be further developed and showcased at the Harbourfront Centre, Theatre Passe Muraille, toured across Canada, and internationally at The Other Festival in Chennai, India.

Most recently, Gregory wrote the book for and directed the acclaimed musical De Profundis: Oscar Wilde in Jail at Soulpepper, which earned six Dora Award nominations. The production won two awards for Outstanding New Musical and Outstanding Performance, in addition to a Toronto Theatre Critic’s Award for Best Direction of a Musical. His play Bremen Town, which premiered at the Next Stage Festival, also garnered six Dora Award nominations, including Outstanding Production, Outstanding Direction, and Outstanding New Play, and will play at the Tarragon Theatre in the fall of 2025.

Other directing credits include Punk Rock for The Howland Company, which was named one of Now Magazine’s Top 10 Theatre Productions of 2018 and earned two Dora Award nominations; Hosanna, which was also listed in Now Magazine’s Top 10 Theatre Productions of 2016; The Heidi Chronicles; and the world premiere of Rose: A New Musical, for which he won the 2019 Dora Award for Best Direction. This production earned 11 nominations and won three, including Best New Musical.

As a collaborator, Gregory was part of creating Alligator Pie, which earned three Dora Award nominations. The production toured across Canada, and in 2017, the cast recording won the Gold Medal for Best Audio Book – Fiction at the International Radio Program Festival in Zurich, Switzerland. He also co-created re(birth): ee cummings in song, which was nominated for a Dora Award for Best New Musical. Both productions were performed in New York City at The Pershing Square Signature Center during Soulpepper Theatre Company’s five-week residency in 2017.

As an actor, Gregory portrayed 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. His acting career includes work with Canadian Stage, Crow’s Theatre, Royal Manitoba Theatre Centre, Theatre Aquarius, 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 also a series regular in the Crave TV comedy Pillow Talk, which earned two Canadian Screen Award nominations.

A passionate advocate for artist training and mentorship, Gregory has taught at institutions such as Toronto Metropolitan University, University of Toronto, The National Theatre School, Neptune Theatre School, Soulpepper Academy, The 519, and various elementary, junior, and high schools across Toronto.

Gregory has been recognized twice in Now Magazine’s Top Ten Theatre Artists of the Year list, has been nominated for eighteen Dora Mavor Moore Awards, and was shortlisted for the Pauline McGibbon Award for Emerging Director. He is a proud graduate of Acadia University, The National Theatre School, and the Soulpepper Academy.

Photo by Dahlia Katz