Michael Healey penning new comedy about the Sidewalk Toronto debacle - plus what else is opening on stages this week across Canada

Playwright Michael Healey, pictured here in 2018, says the story of Sidewalk Toronto has "lots of great narrative in it, big characters."Galit Rodan

The fascinating, failed Sidewalk Labs project in Toronto is already the subject of a bestselling book: Globe and Mail reporter Josh O’Kane’s Sideways: The City Google Couldn’t Buy.

Now, that 2022 non-fiction tome is being turned into a play by one of the country’s funniest and most politically minded playwrights, Michael Healey (The Drawer Boy).

After months of hinting at the project on Twitter, Healey gave this newsletter the scoop that The Master Plan, as his adaptation will be called, has been programmed to open the Crow’s Theatre 2023-2024 season in September. The production will be directed by the company’s artistic director, Chris Abraham.

“Chris asked me if I would read the book, and I said yes as a courtesy,” says Healey, who at the time considered himself “retired” from stage writing.

But the playwright was pulled into the book, which is based on O’Kane’s years of reporting on a Google affiliate’s $1.3-billion bid to turn Toronto’s waterfront into a smart neighbourhood of the future – and the opposition it encountered from privacy advocates and locals before the proposal fell apart in 2020.

“As I spent time with Josh’s book, I came to have a more thorough and nuanced understanding of the proposal and the personalities involved,” Healey says. “There’s lots of great narrative in it, big characters – he even provides me with a couple of scenes that I can just lift out and make my own.”

A cast of seven is set to play what Healey says are The Master Plan’s “enormous number of characters,” only two of which, at the moment, are completely fictional.

Still, he is careful to describe his play as “fiction,” though he also says it will have a strong point of view on what actually went down and be populated by dramatized versions of real players such as Dan Doctoroff, the former chief executive officer of Sidewalk Labs; Will Fleissig, the former CEO of Waterfront Toronto; and John Tory, the former mayor of Toronto.

Justin Trudeau makes an appearance, too, which will make him the third real Canadian prime minister to appear in a Healey play after Proud (about Stephen Harper) and 1979 (about Joe Clark).

When I note that English Canada doesn’t produce as many “recent history plays” as say, England, where David Hare is the master of the form, Healy shares that he reread the playwright’s Stuff Happens just before starting work on The Master Plan. (Healey played George W. Bush in a Toronto production of the 2004 play, which is about the lead-up to the Iraq War.)

The Sidewalk Labs play is being produced in unusually pertinent fashion. Healey started writing in October and provided a first draft of a first act in December. Based on that, Abraham programmed it in his upcoming season (which will be announced, officially and fully, in April). Healey describes this as “an act of extraordinary bravery.”

As for O’Kane, who recently moved from the tech beat to the arts beat at The Globe and Mail, he provided this comment by e-mail about his book being adapted for the stage at Crow’s: “This is extremely tight.”

Other Canadian books on stage: comings and goings

- Room may have met its doom a couple weeks ago, but Life of Pi, a play by Lolita Chakrabarti (Red Velvet) based on the Yann Martel book, still has its big Broadway opening on March 30. The Canadian author will be in attendance as well as, according to a press release, Martha Stewart and Succession’s Brian Cox. I can’t get down but I’ll be interested to read what the New York critics have to say about this show, which already had an Olivier Award-winning run in London’s West End.

- The last chance, for now at least, to see the two-part stage adaptation of Ann-Marie MacDonald’s Fall on Your Knees (reviewed here) is in London, Ont., at the Grand Theatre from March 29 to April 2. (That theatre company just announced its final season programmed by outgoing artistic director Dennis Garnhum.)

- And the final show of Forgiveness, the stage adaptation of Mark Sakamoto’s memoir of that same name, takes place at Theatre Calgary on April 1. (You can find my review of this production, which started in Vancouver at the Arts Club, here.)

Tours opening this week across Canada

- Take d Milk, Nah?, Dartmouth-born Jivesh Parasram’s Governor-General’s award nominated identity play that’s skeptical about identity plays, starts an East Coast tour this week. It’s in his hometown in Nova Scotia on March 29, then goes to Antigonish, N.S., from March 31 to April 1; Sydney, N.S., from April 5 to 8; and Fredericton from April 13 to 15.

This solo show, which I saw in its 2018 premiere at Theatre Passe Muraille, has been on my mind lately after seeing Fairview and The Land Acknowledgement, a couple of other provocative shows examining who’s onstage and who’s in the audience. (I was planning on writing a full review of this Pandemic Theatre production upon its planned return to Toronto in March 2020 – but then the actual pandemic hit.)

- Pretty Woman, a musical based on the old Julia Roberts rom-com about a free-spirited Hollywood prostitute, played on Broadway for about a year starting in 2018. The reviews were decidedly mixed, with many feeling the source material, adapted by an all-male creative team that includes music and lyrics by Canadian rocker Bryan Adams, was past its prime and not in tune with the #MeToo times.

But that’s always made me very curious to see it. The North American tour hits Vancouver this week (March 29 to April 2), then Calgary next week (April 4 to 9), and then Edmonton the week after (April 11 to 16), should you, too, be intrigued.

What The Globe and Mail is reviewing this week

Skyline’s the Limit, Second City Toronto’s first original mainstage revue in its new condo-housed comedy complex, opens to critics on March 30. I’ll be there to check it out and will report back on whether its jokes are NIMBY, YIMBY or MIMBY by the weekend.

First Métis Man of Odesa opens on Friday at the Theatre Centre in Toronto. I’ll be there to review the Punctuate! Theatre production about the Ukrainian-Canadian connection that’s only in town until April 8 before heading to Edmonton and Vancouver.