After graduating from the creative writing program at York University in 1985, Sherman co-founded What Publishing with Kevin Connolly, which produced what, a literary magazine that he edited from 1985 to 1990. Before establishing himself as a dramatist, Sherman's journalistic works such as reviews, essays, and interviews appeared in various publications, including The Globe and Mail, Canadian Theatre Review and Theatrum.
Sherman's first professional productions were A Place Like Pamela (1991) and To Cry is Not So (1991), followed by The League of Nathans (1992, published in book form in 1996), which won a Floyd S. Chalmers Canadian Play Award (1993), and was nominated for the Governor General's Award for English language drama. Among his many other plays is Three in the Back, Two in the Head, which won the Governor General's Literary Award for Drama (1995), and Reading Hebron, which had its most recent production at London's Orange Tree Theatre in March 2011.
In the November 2007 issue of This Magazine, Sherman wrote an article explaining why he would no longer be writing stage plays. Since then, he has written extensively for television and radio, including the CBC Radio series Afghanada and the television series Bloodletting & Miraculous Cures and The Best Laid Plans.
- A Place Like Pamela (1991)
- To Cry is Not So (1991)
- The League of Nathans (1992)
- What the Russians Say (1993)
- Field (1993)
- The Merchant of Showboat (1993)
- Three in the Back, Two in the Head (1994)
- Reading Hebron (1995)
- The Retreat (1996)
- None is Too Many (1997)
- Patience (1998)
- It's All True (1999)
- An Acre of Time (1999/2000)
- Afghanada (2006–11)
- Bloodletting & Miraculous Cures (2010)
- We Were Children (2012); screenplay
- La Ronde (2013) Soulpepper, adaptation by Jason Sherman
- Copy That (2019); commissioned for Tarragon Theatre
- "Sherman, Jason", in The Columbia Encyclopedia of Modern Drama, Volume 2, Gabrielle H. Cody ed. (Columbia University Press, 2007) p1234
- Bill Brioux, "‘Best Laid Plans’ turns satiric focus on politics". Toronto Star, January 4, 2014.
- "We Were Children". Collection page. National Film Board of Canada. Retrieved 17 November 2012.