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Canadian musician Gordon Lightfoot, seen here on April 25, now 80 years old, has been sober since Pierre Trudeau's time in office.Cole Burston/The Canadian Press

On his way to the second-floor space of Early Morning Productions, the Yonge Street office where all of his business affairs are looked after, Gordon Lightfoot would pass a homeless man in the foyer of the building. After giving the man $20 one day, every time thereafter he felt compelled to give him at least the same amount. “I started high,” Lightfoot has explained, “and I just had to continue with it.”

So it is with him, his whole career. Lightfoot started high and everybody expected him to keep up the pace. People – friends, fans, family members, record labels and lovers – took pieces of him and wanted more. A shy, fair-haired boy from Orillia, Ont., an eager-to-please Lightfoot didn’t like to say no. Write us an anthem, Gordon, something about railways. Give us an encore, play us a song, shoot me a loan, would you? Hands were out, all the time. They took his girlfriend, even – the jealousy of Sundown was not baseless.

The pressure got to him. “I was under contract to a record company and I wanted to produce, and that’s what I did.” Lightfoot told Vanity Fair in 2016. “I made sacrifices. The isolation of it all managed to destroy a couple of my [marriages].”

Driven and conflicted by expectations, insecurities, loyalties and immense ambition, he broke down eventually. (And did so well before the abdominal aneurysm that nearly killed him in 2002.) A Canadian Club enthusiast, Lightfoot heckled an audience member at London’s Dominion Theatre in 1981, before walking off the stage altogether. Divorces and drunk-driving happened. Worst of all, after his hit-making heyday, Lightfoot began making bad music.

The singer-songwriter, now 80 years old and sober since the first Trudeau prime minister, is the subject of a new documentary, Gordon Lightfoot: If You Could Read My Mind. Named after one of his signature songs, the title alludes to his complexity and, according to one of the film’s directors, his impenetrability. “There’s no easy answers with him,” says Martha Kehoe, who made the film with fellow Torontonian Joan Tosoni. “He just isn’t prepared in that moment, with the camera on him, to do any kind of self-mining.”

The biodoc’s telling early scene has Lightfoot and his current and third wife, Kim Hasse, watching an old clip of him singing (That’s What You Get) For Lovin’ Me. We see Lightfoot wincing at the song’s blatant misogyny, before telling the directors to turn the thing off. “I guess I don’t like who I am,” he says, in a rare moment of introspection.

“It’s not a free ride being Gordon Lightfoot,” Kehoe told The Globe and Mail. “You have regrets. You’ve done stuff. You’ve screwed people over. You’ve put yourself first. You’ve believed your own fame. He doesn’t want to articulate it in every way that that is true, but if you spend time with him, it’s all there, somewhere.”

He spoke about some of those regrets when I visited him in his airy mansion in the city’s tony Bridle Path neighbourhood. In his small wood-panelled study and songwriter space, a gaunt but willing Lightfoot was comfortably surrounded by 12-string Gibson guitars, Fender amplifiers and cassette recorders as old as his last hit.

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Burton Cummings says Lightfoot should be part of Canada's history-book curriculum.Michael Ochs Archives/Courtesy of Hot Docs

The Globe and Mail: Tell me about (That’s What You Get) For Lovin’ Me.

Lightfoot: It’s a song about unrequited love. I didn’t understand what the word chauvinism meant when I wrote it. I was married at the time. It could have been offensive, but my wife, Brita, was European. She understood what poetic licence was, I suppose.

Globe: Would you write a song like that today?

Lightfoot: Probably not. I would take the brutality out. You don’t want to create emotional trauma to people who are close to you. You have to be careful what you say when you’re writing a song. It’s the songwriter’s curse.

Globe: The song was covered by Johnny Cash and Peter, Paul and Mary. Is that the ultimate compliment, for a songwriter, to have one’s work recorded by others?

Lightfoot: Yes. I think you could say so. I still ask the question “why?” though.

Globe: You wrote good songs, that’s why. Why would you ask such a thing?

Lightfoot: Because I still question my own ability. I have my whole life, and I continue to do so.

Globe: Is that healthy?

Lightfoot: I don’t know if it helps or not. Did you say “helping” or did you say “healthy?”

Globe: Healthy.

Lightfoot: I don’t consider myself to be a genius, by any stretch of the imagination. It bothers me to be referred to as such.

In the documentary, Lightfoot is not specifically referred to as a genius, though Burton Cummings does say the Canadian Railroad Trilogy songwriter should be part of this country’s history-book curriculum. Canada chronicler Pierre Berton never rhymed “Gitche Gumee” with “the skies of November turn gloomy," and it was Lightfoot, not Tom Thomson, who wrote A Painter Passing Through.

When the lights were raised following the film’s first public screening at TIFF Lightbox, an older gentleman stood up and raised his walking cane in the air. “Let’s hear it for Canada’s one and only, Gordon Lightfoot,” he so much as hip-hip-hooray-ed.

Seated on one side of me at the screening was Bernie Finkelstein, something of a Canadian music legend himself. I asked him if he knew who the man with the cane was. “I don’t,” he replied. “But I don’t like him. I can’t stand cheerleaders.”

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Lightfoot chose to stay in Canada, unlike Joni Mitchell and Neil Young.geoff george/Courtesy of Hot Docs

Finkelstein, who started True North Records in 1969 and who still manages Bruce Cockburn, used to promote shows with Lightfoot’s long-time friend and booking agent, Bernie Fiedler. Asked if Lightfoot was a Canadian icon under siege with expectations early in his career, Finkelstein agreed. “Canadians want their artists to succeed in the United States,” Finkelstein answered. “It’s important to them.”

Where Joni Mitchell and Neil Young left the country early in their career, Lightfoot stayed in Canada. He became the home team. Mitchell wrote Help Me, Young wrote Helpless, and Captain Canada, the canoe-tripping troubadour, wrote Carefree Highway and record-setting alimony cheques.

But when asked if the demands asked of Lightfoot were unreasonable, Finkelstein waved off the premise. “I’m not sure being a millionaire songwriter was ever all that hard,” he said. “These artists get a lot of phone calls, but I don’t think any of them are going to say it’s upsetting. The only complaints from them I ever heard backstage were about the cold-cut platters.”

Seated on the other side of me at the screening was Bruce Good, a musician who has known Lightfoot since the late and 1960s and who had a more sympathetic understanding of the pressures Lightfoot faced and still faces. “He realized people wanted a piece of him,” said Good, featured in the film, speaking about how Lightfoot’s wistful 1968 toe-tapper Did She Mention My Name makes his eyes well up to this day.

As part of the seminal Canadian folk-rock group the Good Brothers, Good has faced some of the pressures that Lightfoot does, though on a much smaller scale. “If I’m walking through a crowd of people at a concert, I put the blinders on, because I know if I make eye contact, they’re going to ask me something or want something. I can hardly imagine what it’s like to be Gordon Lightfoot.”

What it is to like be Lightfoot is to be asked of constantly. “Here comes mister cool along the walk of fame, I was in demand, always in control,” Lightfoot sang on 1998′s autobiographical single A Painter Passing Through. “The world was in my hands, my touch had turned to gold.”

Back in the 1970s, when the Sometimes When We Touch star Dan Hill needed a Learjet in the middle of the night in Moncton, he called Lightfoot.

After an indie-rock band recorded Lightfoot’s Great Lakes standard The Wreck of the Edmund Fitzgerald, one of the band’s musicians got upset when Lightfoot refused to recognize the cover version and accused him of lifting the song’s melody.

In 1966, with Canada’s centenary approaching, CBC needed an instant folk classic that captured the glory of the country’s spike-driven origins. Fuelled by coffee, cigarettes and a fat commission, Lightfoot wrote Canadian Railroad Trilogy in three days.

That same year, at a summer post-show party in Toronto, the star Canadian folkie Ian Tyson approached his friend Lightfoot at four in the morning. Earlier in the evening, Lightfoot had a introduced a new song to a crowd at the Riverboat coffee house.

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When asked about new songs, Lightfoot retrieves the lyric sheets to a couple of unrecorded songs he’s been working on.Cole Burston/The Canadian Press

“It’s a good one, Gordon,” Tyson said to Lightfoot at the after-party. “What it’s called?” Informed the song was Go My Way, Tyson made a request. I’d like to hear it again. Why don’t you go and get your old guitar and play it for me?”

A sleep-deprived Lightfoot acquiesced. There was no end to the requests made upon him.

A young John Macfarlane, who would go on to serve as editor of Toronto Life and the Walrus, was a music writer for The Globe in the 1960s. He was at the party where Lightfoot played for Tyson, and included the story about it in a Globe profile, one of the first major Lightfoot features ever published. “It struck me as an important Canadian moment,” Macfarlane recalled recently.

In Macfarlane’s interview with Lightfoot, the 27-year-old songwriter described himself as a “cosmopolitan hick” and a “country boy, doin’ the best I can.” As if he were a rube – or worse, a John Denver.

“I think that was a glib way of shutting down any further discussion,” said Macfarlane, who back then almost rented an apartment in the three-story home Lightfoot shared with his wife, before the couple wisely decided against sharing a house with a journalist. “He was learning how to deal with incursions into his psyche, which were not welcome. He was a working man, and his work was music.”

Indeed, sit-downs these days with Lightfoot rarely result in much reflection. However, when asked about new songs, the songwriter (who hasn’t put an album of fresh material since 2004’s Harmony) gleefully pops out of his chair to retrieve the lyric sheets to a couple of unrecorded songs he’s been working on for a new album. One of them is called The Laughter We Seek. The other one has the line, “I’ve got one too many women in my life.”

Lightfoot crows about the latter song: “How’s that for an idea, eh? Now, how would I come up with something like that?”

When it is suggested that a song about one woman too many would seem to be in the vein of For Lovin’ Me, the kind which he said he’d never write again, Lightfoot is quick to protest. “No, it’s not!” he says quickly. “That was a hurtful song. This is not hurtful. This is whimsy, you see?”

After the interview, we stand in his vaulted front hall, where some of the cast fixtures look out of place. Turns out Lightfoot had salvaged the pieces from the Rosedale mansion where he once played host to Bob Dylan, Ramblin’ Jack Elliott and all the others. “I didn’t want to leave that house," Lightfoot laments. So, why did he? “It was my former wife’s idea, to get away from downtown distractions.”

When asked if he’ll play the first concert at Massey Hall when the venue, currently undergoing extensive renovations, re-opens next year, Lightfoot eyes brighten. “I don’t want to hog the stage,” he says. “But if they want me to do it, I’ll be there.”

Lightfoot obliges, as he does.

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