"If you can't sleep, how can you tell you're awake?" With this apparently simple question, Daniel Brooks and Guillermo Verdecchia revisit their "purposefully puzzling rumination on life's anxieties," as a Globe and Mail review described its world premiere in 1998. Necessary Angel Theatre Company presents a new production of Insomnia to be directed by its artistic associate, Chris Abraham, and featuring Fiona Highet, Randy Hughson and Brooks himself as John F., the artist tossing and turning in and out of bed as he faces a failing marriage, a troubled career and an unfinished masterpiece. Nov. 7 to Nov. 26. $20 to $35. Buddies in Bad Times Theatre, 12 Alexander St., 416-975-8555, http://www.buddiesinbadtimestheatre.com , http://www.necessaryangel.com .

The incomparable Tom Walmsley returns to Theatre Passe Muraille with his third new play this year (after 3 Squares a Day and Delirium) and the third to be directed by Kate Lynch in as many years. A poet and a party animal (both named Randy) are ensnared by a woman who wants "one last savage night" before a life of marriage and monogamy. Expect the same exploration of sex and religion (and their inherent connections) that made 3 Squares a Day in particular so compelling. Cast includes Deb Hay, Christopher Morris and Paul Fauteaux. Oct. 21 to Nov. 19. $10 to $30. Theatre Passe Muraille, 16 Ryerson Ave., 416-504-7529, http://www.passemuraille.on.ca .

Vern Thiessen, one of Alberta's leading playwrights and a Governor-General's Award winner (for Einstein's Gift), makes his belated Toronto stage debut with Apple, a portrayal of a marriage "on the brink of destruction and reconstruction." Under Ken Gass's direction, Kevin Hanchard plays Andy, the husband whose shaky marriage to Evelyn (Sarah Orenstein) goes through two more turbulences: a sexy medical intern by the name of Samantha (Niki Landau) and Evelyn's breast-cancer diagnosis. Oct. 14 to Nov. 12. $12 to $35.50. Factory Theatre, 125 Bathurst St., 416-504-9971, http://www.factorytheatre.ca .

This is the world premiere of a new musical from the team of Neil Bartram and Brian Hill to be directed by Michael Bush of New York's Manhattan Theatre Club. A two-hander in one act, The Story of My Life celebrates the lifelong friendship between Alvin and Thomas (Jeffrey Kuhn and Brent Carver, in his first role after The Lord of the Rings debacle) who met in Grade 1 and shared the "battlefields of childhood and adolescence." Oct. 30 to Dec. 9. $20 to $55. CanStage Berkeley Street Theatre Downstairs, 26 Berkeley St., 416-368-3110, http://www.canstage.com .

An unexpected rave from The New York Times turned this existential monologue from American playwright Will Eno from yet another experimental play -- a "little performance . . . on the themes of fear, boyhood, nature, hate, the nature of performance. . ." -- in Lower Manhattan into a cult phenomenon that made the Pulitzer Prize short list in the spring of 2005. The writing, as I wrote when I reviewed it then, is "fresh and stunning," but some of its theatricality is stuck in 1980s postmodernism. For this Toronto premiere, Jennifer Tarver will direct Tom McCamus -- a pairing of two powerful theatrical minds. Nov. 7 to Dec. 17. $18 to $32. Tarragon Theatre, 30 Bridgman Ave., 416-531-1827, http://www.tarragontheatre.com .

Nobody does Harold Pinter (or drama from the second half of the 20th century in general) as consummately and in as theatrically airtight terms as Soulpepper. This claustrophobic 1960 play is vintage Pinter and features three characters (to be played by Damien Atkins, Matthew Edison and Diego Matamoros) struggling over the physical and psychological ownership of a London walkup flat. Albert Schultz will serve as director. Oct. 26 to Nov. 25. $25 to $54. Young Centre for the Performing Arts, 55 Mill St., 416-866-8666, http://www.soulpepper.ca .

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