‘He looked hot, … like a young Maggie Smith’

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If you're looking for an actor to star in Guys and Dolls – well, Kyle Blair has all the bases covered.

In what is surely one of the strangest casting coincidences of all time, Blair first played missionary Sarah Brown in a quirky, cross-gendered production directed by theatre critic Richard Ouzounian at Talk Is Free Free Theatre in Barrie, Ont., last fall.

And now, in the large-scale revival directed by Poland's Tadeusz Bradecki that opens on Saturday at the Shaw Festival, Blair has reversed roles to play Sarah's romantic partner, gambler Sky Masterson – and is singing the other line in duets like I've Never Been in Love Before and I'll Know (When My Love Comes Along).

As far as anyone can tell, the 35-year-old native of London, Ont., is the first actor to ever play both the lead guy and the lead doll in Frank Loesser's 1950 musical in a single season. Indeed, he is likely the first to play both professionally, ever.

Blair admits the experience has been slightly disorienting – at least, it was when he started rehearsals opposite Elodie Gillett's Sarah in Niagara-on-the-Lake, Ont., earlier this spring. "It was really annoying because I knew all her lines and none of mine," he recalls.

"But to live within that writing for that long has been a gift for me – it's very smart and specific."

While those involved in hiring Blair for the two Guys and Dolls productions insist this is a fluke rather than a stunt – he was cast in the role of Sarah in Barrie before Shaw artistic director Jackie Maxwell announced he was to play Sky – it also seems like they're talking about two entirely different Kyle Blairs.

Maxwell first thought of Blair for the part of the cool, crafty high-roller after seeing him play one of Mr. Doolittle's Cockney sidekicks in My Fair Lady two years ago. "I loved him in that because he was so edgy and a little bit scary," says Maxwell. "I think you've got to believe that there's a little bit of danger with Sky."

Meanwhile, Arkady Spivak, artistic producer of Talk Is Free, says Blair came to mind immediately for the role of the earnest missionary as he and Ouzounian were looking for a male actor with "natural sweetness" and "simple beauty." "He plays simply wholesome people – and that's what Sarah Brown is," says Spivak.

Who is this actor both "edgy" and "wholesome"? Blair, a graduate of the University of Windsor's musical-theatre program, is a triple threat with great comic timing who has been the rope in a theatrical tug-of-war between Stratford and Shaw in recent seasons – flitting back and forth between the two festivals.

Still, just as the in-demand actor wasn't expecting ever to play Sarah Brown, he didn't think Sky Masterson was in the cards either. "I wasn't sure if people would see me in that role," Blair says. "I've played a lot of the juvs."

That's musical-theatre slang for "juvenile roles": Naive young men like Frederic in Pirates of Penzance, Billy Lawlor in 42nd Street and Will Parker in Oklahoma! – all of which Blair has played at Stratford.

Indeed, Sky Masterson is a part regularly taken by older, gruffer male actors – who then have a habit of never letting it go. (Scott Wentworth, who played Sky at Stratford in 1990 and 2004, returned to the role in 2012 at Montreal's Segal Centre.)

But, as Blair points out, while Sky is certainly smart and shrewd, he's also much younger than often portrayed, especially if you go back to the original source material of Damon Runyon's short stories. "He is maybe 30 years old, and is a tall guy with a round kisser, and big blue eyes, and he always looks as innocent as a little baby," Runyon wrote in The Idyll of Miss Sarah Brown, the 1933 short story that lends its plot to Guys and Dolls.

That could be a fair description of Blair. Sarah Brown, however, was further out of his comfort zone – he'd never played a woman before and found it hard to navigate the eyelashes, the heels and the dresses. (He squeezed into Cynthia Dale's costume from the Stratford 2004 production, rented for the Barrie one.) "I didn't know what to do with my hands.… I haven't felt [that] in a long while," the actor recalls.

According to Spivak, Blair acquitted himself well in Ouzounian's production – which he says was not campy, but aimed to show that classic musicals can be shaken up the way classic plays are. "He looked hot," Spivak insists. "He looked like a young Maggie Smith."

While the Barrie production implicitly challenged the musical's ideology about guys and dolls, Bradecki's big-budget take at the Shaw Festival is playing it straight. The Polish director says Loesser's musical is such a "precise construction" that there is no space for directors' concepts. "In our production men play men, women play women, and the action takes place on Broadway in the early fifties, exactly how Frank Loesser wanted it to be," he says in an e-mail from overseas.

But can we still relate to the simplistic division of gender roles in Guys and Dolls? Like many musicals from the postwar period of Broadway, it can almost seem like heterosexual propaganda – with the leading ladies conniving to "marry the man today," and the title tune explaining that men all give up their roving ways to become breadwinners: "Call it sad, call it funny – but it's better than even money, that the guy's only doing it for some doll."

Having seen the play from both sides now, Blair, whose partner, Kyle Golemba, is also in the cast, believes the musical still resonates. "I've been thinking about Taming of the Shrew a lot, because I think there's a similar challenge in that play," he says. "Ultimately for me, the story is about finding an authentic way of living for these people.… There's so much joy in it."

Guys and Dolls, now in previews, runs from May 11 to Oct. 12 at the Festival Theatre in Niagara-on-the-Lake, Ont.

THREE TO SEE AT SHAW

The Shaw Festival officially opens its 52nd season with Guys and Dolls, Bernard Shaw's Major Barbara and Somerset Maugham's Our Betters. Here are three of the more promising-looking shows also scheduled for this season.

Trifles, Court House Theatre

The Shaw Festival's lunchtime one-acts are often the strongest of the season – and this year, there are two. West Coast director Meg Roe visits to tackle Susan Glaspell's masterful 1916 miniature Trifles, as well as a Eugene O'Neill rarity of similar vintage called A Wife for a Life. Previews from May 29, opens June 8, closes Oct. 12.

Faith Healer, Royal George Theatre

Irish playwright Brian Friel tells the story of a visit by a faith healer to a small town, in three Rashomon-esque monologues. Craig Hall directs two of Shaw's top talents – Corrine Koslo and Jim Mezon. Previews from June 13, opens July 12, closes Oct. 6.

Arcadia, Studio Theatre

With the Shaw Festival now exploring contemporary playwrights, it was only a matter of time before they turned to the works of brainy Brit Tom Stoppard. Eda Holmes directs this clever romance about poetry, math and gardening that hops between1809 and the present day. Previews from July 14, opens July 27, closes Sept. 7.