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William Shatner was understudy to Christopher Plummer as Henry V at the Stratford Festival in the 1950s.Kevin Van Paassen/The Globe and Mail

We were going back to William Shatner's 20s and the early days of his stage career at the Stratford Festival, but somehow we got sucked back further, all the way to his primary school days in Montreal.

Now, Shatner's back playing conkers with horse chestnuts, shooting BB guns and running with the Marcil Avenue gang – with Peanuts, Guy and, of course, Betty.

"Betty was my entrée into sexuality, not necessarily sex, but being aware of a voluptuous girl," says the 82-year-old actor, in that halting, awestruck tone, as if testifying to a miracle. "We used to play tackle football – and, if you tackled Betty, it could change your life."

Shatner is providing this peek into his pubescent past at the Four Seasons in Toronto, the afternoon before he is honoured there by the Stratford Festival with its Legacy Award. Oddly, it doesn't feel like oversharing: He's warm, he's funny; and he's definitely on. "Did you run up and down the stairs?" he says, after I tell him we went to the same elementary school. "Did you ever get strapped? Did you look out the window a lot and dream?"

It's not all that different from listening to the lyrics – which hover between winkingly larger-than-life and painfully earnest – on Shatner's latest disorienting album.

Produced with members of the progressive rock band Yes, Ponder the Mystery features Shatner marvelling at the long, strange life he's lived in a rococo recitative intoned over noodling guitar lines. Sample song titles: Where It's Gone… I Don't Know; Change; Sunset and Where Does Time Go?

So, it's not just the Stratford award – for the three seasons he acted as part of the company in the 1950s – that has him pondering how exactly William Shatner of Montreal ended up as William Shatner, the Emmy-winning actor, the pop-culture icon, the man who helped usher in the era of meta-celebrity.

Back then, Shatner wasn't yet Shatner, just as Stratford certainly wasn't yet Stratford. In 1953, he turned down an offer to be in the legendary first season of the Ontario theatre company starring Alec Guinness as Richard III because he had work lined up elsewhere.

In the summer, the young McGill business school graduate would act in light comedies at the Mountain Playhouse at the top of Mount Royal in his hometown. In the winter, he'd go to Ottawa and do the heavier stuff at the Canadian Repertory Theatre. He didn't want to jeopardize that.

At that time – it was the birth of professional theatre in Canada as we know it – Stratford wasn't an institution. It was a risk and anybody's guess what would survive.

This helps explains the tone of astonishment that Shatner adopts when he talks about the festival. Unlike previous Legacy Award recipients Christopher Plummer and Maggie Smith, Shatner was never a star there. The most famous anecdote from his tenure was when he went on as understudy to Plummer as Henry V – the future Oscar-winner was in the hospital, on morphine, having a kidney stone out – without ever having had a proper rehearsal.

But mostly Shatner was a middle-of-the-pack player, earning about $50 a week, tackling hard-to-place characters with Italian names like Gratiano and Lucentio. "I lived in a tiny downstairs room with a horsehair sofa and a very narrow bed and you had to get out of there to breathe and to study," says Shatner, once he's coaxed off the subject of his Montreal childhood. ("I wonder if Betty ever went to Stratford to see me.")

By 1955, Shatner – who, unlike many fellow company members of the time, didn't drink and avoided women – had diligently saved up $500, which he planned to use to go to New York. But then came a fateful trip to the local stock exchange with his Merchant of Venice co-star, Lorne Greene – whom, he recalls, he "followed around like a hound dog." After the older actor suggested putting his money in uranium stock, Shatner decided to take the tip; it wasn't a good one, and he quickly lost his life savings.

"All I could think of during my Friday night performance, and Saturday matinee and Saturday night's performance was I'm wiped out, my entire savings is gone, I'm back to being poverty-stricken," Shatner recalls. "It was then that I made a vow I would never gamble like that again, because my performances were affected."

There's one possible end to Shatner becoming Shatner. He could have slunk back to Montreal and used his business training to make up the loss. But, returning to Stratford in 1956, his dream of going to New York was satisfied when the company's production of Christopher Marlowe's Tamburlaine transferred to Broadway for a limited run. He played a character called Usumcasane, which is a joy to hear coming out of Shatner's mouth. (Usumcasane! U-sum-ca-SANE!")

Agents and producers came to see the show and, as Shatner says, "to make a long story shorter, I, in effect, stayed in New York and started my career in the United States."

What's past is prologue – 1956 is when the story of William Shatner as we know him begins: The Twilight Zone, Captain Kirk, T.J. Hooker, Rescue 911, Priceline, The Practice and Boston Legal; four wives, three children, two Emmys and a Golden Globe.

1956 was also the year the Canadian Repertory Theatre closed down. The Mountain Playhouse was demolished in 1962. Stratford still stands 60 years later, and so does Shatner.

As our interview ends, I tell the actor that I wanted to see his one-man show on Broadway (now on Movie Central), and was sorry to not make it down.

"That's the curse of wanting to do something and missing it," Shatner says. "You've got to do it." Insert prog rock music here.

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