On a Sunday night, we’d hop on the motorbikes and take the back road along Gouin and head for the Yellow Door coffee house. It was about a 45 minute ride depending on traffic and construction which meant that we would be back late, but Sunday was Hootenanny night and that meant the possibility that one of our favorites might show up to perform one (or more) songs. And topping that list was Jesse Winchester. We often went downtown for an act that we liked on Fridays – Jesse, Bruce Cockburn or even Penny Lang. But Jesse was always top of the list.

Jesse was a draft dodger from the Louisiana who had arrived in Montreal in 1967 with$300 in his pocket and was making a tentative living doing the coffee house circuit in eastern Canada. He was a pretty good guitar player (unlike most in the circuit he had gone electric and had to carry his amp and speaker on stage with him), a wonderful singer and one of the great songwriters of his generation. If there is any way for you to do it, you should be listening to “Biloxi”, “Yankee Lady”, “Black Dog” and “Brand New Tennessee Waltz” while you are reading this. They are all on his first album and we got to hear them live a lot of times.

We were all in either the last year of High School or at University but still living at home in the burbs. Motorcycles were big in our lives and the guys that owned them gave lifts to those of us who didn’t. We’re not talking Harleys here, just Kawasaki 350’s at the biggest, but fun and freedom – even for us perpetual passengers. I had often thought, then, that I should ditch McGill and get an entry-level job, so that I could own my own bike. I wonder, now, how seriously I had considered that idea. But then, we were all at a point in our lives when we were facing some major decisions that would have huge impacts and we had no idea exactly what those impacts would be.  

Jesse was an odd sort of draft dodger. Although he was against the war he was not a hippy or a druggy type, in fact he had studied philosophy, spoke German and believed in the concept of sin. He was a choir-boy Catholic and despised those that took drugs. He thought that most of the music of his era was crap. He said:

“Well, when I went to Montreal, it was in 1967, and this was the – really, the whole counter-culture hippie movement was really getting into high gear at that point. And musically, what that turned out to be, I’m thinking mainly because of the drugs that everyone was consuming, it turned out to be songs that involved, you know, ten minute electric guitar solos that began nowhere and wound up nowhere. You know, no cohesion in the music at all, to my ear. And I think the music of that period was terrible. I just can’t stand it. I think the Beatles lost whatever magic they had at the beginning, during that period. I just think people went crazy musically, and every other way. But we’re talking about music now, and what happened was, a group called The Band came along. They had been accompanying Bob Dylan, and they made an album called “Music from Big Pink,” which had structure, interesting arrangements, lyrics, all the things that I wanted in music. They were essentially a conservative movement in music. Back to respect for your elders, belief in God, close to the land, all these things, all these conservative values. That’s what they represented, to me, at least.”

So what was he doing being a draft dodger? "I was so offended by someone's coming up to me and presuming to tell me who I should kill and what my life was worth," he told Rolling Stone magazine in 1977. So, based on that moment of personal integrity, he moved to Montreal and, despite Jimmy Carter’s limited amnesty in 1976, he had to live in Canada until 2002. He got lucky and met Robbie Robertson and, with Robertson producing, he cut his first albumin 1970. After that, Jesse lived, loved, recorded and wrote in Canada with only extremely limited access to the American market.

1976 was a crucial year for the guys that made up the Yellow Door convoy each Friday and Sunday. We had all moved on in one way or another but the sad truth was that the election of the Parti Quebecois was the end of our group, at least for me. The departures began with the parents. The mothers and fathers of every friend that I had in High School left Quebec in 1976 or thereabouts and very soon thereafter their children followed. Today I know only one High School friend or acquaintance that still lives in Quebec. Most went as far as you could go and ended up in B.C. They all stayed in touch with each other, I stayed here.

Jesse continued writing music and recording albums but there was no breakthrough hit and no popular success. Because he could no tvisit the States he could not promote his albums with extensive touring. But a great number of American artists including James Taylor, Lyle Lovett, Lucinda Williams, Rosanne Cash and Jimmy Buffett recorded his songs and loved his music. By the time he could visit the U.S. with complete freedom, the era of the singer-songwriter (a la James Taylor) was over. Some of his music was used for television (The Wire) and he seems to have been comfortable, but the shot at the stardom that his talent deserved was gone. Jesse died of cancer in 2014, at his home in Charlottesville, Virginia.

We never know how consequential our decisions can turn out to be. And sometimes the road taken turns out to be the right one after all. We never know. Robert Frost said it best:

The Road Not Taken

BY ROBERTFROST

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

Then took the other, as just as fair,

And having perhaps the better claim,

Because it was grassy and wanted wear;

Though as for that the passing there

Had worn them really about the same,

And both that morning equally lay

In leaves no step had trodden black.

Oh, I kept the first for another day!

Yet knowing how way leads on to way,

I doubted if I should ever come back.

I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I—

I took the one less travelled by,

And that has made all the difference.

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