When I was 17, my dad introduced me to his new girlfriend, a woman called Anne. She was in her 40s and was in the habit of punctuating everything she said with one of those smoker’s laughs that sound like a cough. When my dad went into another room to take a phone call, she asked if it was true that I liked music. I said it was. She told me that ‘Gordy’ Lightfoot had written a song about her. Really, I said, which one? Sundown, she told me. Isn’t that about a prostitute? I asked. When my dad returned, Anne said, ‘I think your son just called me a hooker.’ It was awkward.

Sundown is a heavy song. It was always on the radio when I was growing up in Canada in the 1970s but I never took much notice of it. When I began to listen to Lightfoot more seriously as an adult, I was struck by its darkness. The singer pictures this woman in various outfits and is filled by jealously and self loathing. In the end, alcohol is his only refuge. There is something oddly vulnerable about it. The singer seems powerless and doomed. Even his veiled threats – you better take care – sound hollow.

And it turns out that the song was not an ode to my dad’s girlfriend. In Nicholas Jenning’s new biography, Lightfoot, we learn that the song is almost certainly about Cathy Evelyn Smith. Sound familiar? Yes, the same woman who went to jail for her involvement in John Belushi’s death at the Chateau Marmont. If you have read Robbie Robertson’s memoir, you may remember her in connection to Levon Helm but that really is another story.

Where I come from, Gordon Lightfoot is bigger than…well, just about anyone. Put it this way, a lot of Canadians who wouldn’t know a Neil Young song if one backed over them could probably easily name 10 Lightfoot songs. I remember my grandfather throwing Gord’s Gold into the 8 track player and letting it play over and over all day. I can also remember the Canadian bands I loved in the 1980s name checking him in interviews and playing his songs in encores. He played Massey Hall every year to audiences that included Bay Street lawyers, Scarborough tow truck drivers, hippies, punks, Social Studies teachers, and glad handing politicians. He could have run for Parliament, he could have been crowned king.

However, the living legend status is something of a consolation prize for a singer whose viability as a recording artist came to crashing halt in about 1980. He kept making records but people stopped buying them. I own everything he released up to and including Endless Wire, which appeared in 1978. I had never even heard of the follow up, Dream Street Rose or any of the subsequent records before reading this book. I suppose there are superfans that would snort at my amateurishness here but the sales figures tell the same story. Thanks for all the great songs, Gord. Here’s your gold watch. The man was 42!

Lightfoot is a solid, chronological account of Gord’s life and work. It is a respectful and workmanlike book – rather Canadian, really! There are no startling revelations or particularly original insights. Instead, Jennings strives to build the character of the man through a number of significant episodes. Lightfoot is a very private fellow with a certain reputation for difficult behaviour. He has been married many times and has had troubles with alcohol. Jennings draws a picture of a hard working and shy man who couldn’t have been less temperamentally suited to stardom. He grew up in Orillia Ontario, a town probably not so different to Hibbing Minnesota. Unlike Hibbing’s favourite son however, Gord was never headed for Malibu via New York. I was interested to learn that throughout his long career he has always lived in Toronto. He spent years living on Alexander St, behind Maple Leaf Gardens, before moving to Rosedale. These days, he lives on Bridle Path, a glamorous address by Toronto standards but hardly Malibu.

Jennings explores Lightfoot’s relationship with Bob Dylan in some detail. Dylan is a fan, no question. There is a small group of songwriters that Dylan admires. He is generous but fickle on this topic in interviews. Sometimes he mentions John Prine, sometimes it’s Jimmy Buffett (no, really, he said that once) but the name that consistently comes up is Gordon Lightfoot.

Lightfoot has taken a different path from Bob in many respects. He was never the voice of a generation or a rock god. He never partied at the Factory or fell to pieces in the back of a Rolls with John Lennon. Gordon Lightfoot’s career has been comparatively low key. In the flashy dramatic world of popular music, there has always been something subtle about him. His albums, particularly the early ones, are quiet affairs. A small band, some strings here and there, and minimal overdubbing. I used to wish that Bob Johnston had produced at least one record for Lightfoot in the sixties. Are we rolling, Gord? But, maybe I’m happy that he didn’t. His 1970 Sit Down Stranger album, quickly renamed If I Could Read Your Mind after its most famous song, is a case in point. To me, this album is what Self Portrait should have been and is perhaps a glimpse of what Dylan had in mind. It was recorded in LA but there is a distinctly Nashville sensibility to it. It’s easy to see why Kris Kristofferson and Johnny Cash were such fans. The songs are beautifully written and unobtrusively performed. From MOR to Outlaw Country to the Laurel Canyon songsmiths, this was a masterclass in showcasing your work.

But back to Dylan. Bob doesn’t always work well with others and his relationship with Gord had always been cordial, if guarded. When the Rolling Thunder Tour pulled into Toronto in early December of 1975, Gord was asked to play the second last set in the program. He played The Watchman’s Gone and Sundown. Try to imagine following that on a Toronto stage. Bob Dylan might have been the only person on earth in those days with a chance but I’m willing to bet that his set was something of anti climax. Anyone who was there is welcome to correct me!

After the show, everybody, and I mean everybody, went back to Gord’s place in Rosedale. The party was legendary. Mick Ronson was there, trading stories with Ronnie Hawkins. Joni Mitchell and Joan Baez were avoiding each other while all eyes were on Scarlet Rivera. Then that lovable scamp Bobby Neuwirth threw his leather jacket into the fireplace and filled the whole house with black smoke. What a fun guy. See if he’s available for your next soiree.

Meanwhile, Bob and Gord had retreated to the parlor to jam. The wildest rock and roll party in Toronto history was unfolding downstairs but Dylan and Lightfoot were quietly exchanging songs. Oh, to have a decent recording. Alas, there is only a fragment of Lightfoot singing Ballad in Plain D, of all songs. Lightfoot is a remarkable man but the fact that he knew the words to Ballad in Plain D might just make him some kind of superhero. In any case, as Jennings points out, neither man was there to party. This was a summit meeting. Everyone has seen Bob’s exchange with Donovan in Don’t Look Back. This was not like that.

“Hey Roger, he knows Ballad in Plain D!”

I suppose Jennings uses this episode to highlight the depth of Gordon Lightfoot’s commitment to songwriting. Sometimes, while reading, I had the sense of a man who might have preferred playing to a crowd of receptive regulars at his neighborhood pub to touring the world as a superstar. In one telling episode that took place in the 1970s, Gord signed on with a famous agent who managed a number of mainstream stars at the time. He wanted to take the singer to the next level where he would be on television, headlining regularly in Vegas, and selling zillions of records on the back of duets with divas, etc. After a few days, Lightfoot got cold feet and asked him to tear up the contract. He didn’t want to be Kenny Rogers or Tom Jones. Instead, he started taking the Toronto subway to the gym because he felt bad about the environment.

Nicholas Jennings had some access to the occasionally prickly singer while he was writing the book. It’s hard to imagine that such a modest and private man will ever write a memoir so this might be as close as we get. If you are a fan, don’t forget to read Dave Bidini’s utterly brilliant Writing Gordon Lightfoot too. There you go, you can ask for both for Christmas and spend Boxing Day on the couch reading while everyone else watches college football.

Meanwhile, Gordon Lightfoot will no doubt be playing his annual gig at Massey Hall and releasing a new album this year. Last week he was in Peterborough donating his canoe to the Canoe Museum there. A Canadian legend? You bet.

Teasers: The whole story behind If I Could Read Your Mind; his early days as a singing sensation in Orillia, Ontario.