How Ron Sexsmith ended up singing with Leonard Cohen in an Indigo basement

Canadian songwriting legend Ron Sexsmith has turned 60, and will be celebrating the milestone with a concert at Massey Hall Thursday.

A favourite of legends like Paul McCartney and Elvis Costello, Sexsmith has headlined the iconic venue multiple times. 

“It just became sort of my favourite thing really to do as a Canadian, to go to Massey Hall and hear Gordon’s voice,” Sexsmith told Day 6 guest host Manjula Selvarajah. “Back in the old days when I was a courier where I couldn’t afford a ticket and I would listen to the show by that stage door … It was one of those venues that I felt I could get there someday.”

In a career spanning setlist, the songwriter will be pulling from his four-decades-old songbook. 

In a conversation with Selvarajah, Sexsmith elaborated on his long career, and some of the stranger collaborations he has had with other musicians. 

Here is part of that conversation.

What is it about this particular milestone, turning 60, that made you want to have this retrospective type of concert? 

A few years back, 60 was looming, and I was kind of dreading it, like a lot of people would. But I didn’t want to dread it, I wanted to try to sort of embrace it … I thought maybe I should do just some kind of playlist, or I thought maybe the label might be interested in doing some kind of retrospective album, but there’s not, with my career, there’s not a lot of incentive, you know, from people to do stuff like that.

WATCH | Ron Sexsmith reflects on his career at 60

And so I really started thinking, maybe I could do a show and get my band. I haven’t played with my band since 2018.

When you talk to, most sort of musical enthusiast music critics, they’ll say that Ron Sexsmith is a critical part of the Canadian songbook. What do you say to that? 

But it’s hard to know really where I stand in the whole thing. And, you know, sometimes I don’t really know if my contribution has much value, actually. And I mean it. You live in your head so much, you really don’t know. You know how it all sort of shakes out in the end. But I’ve definitely tried to have a body of work. I’m really proud of the music I’ve made, and I feel my career has been pretty interesting, you know? I mean, I’ve met most of my heroes. I’ve had my songs covered by a lot of people. So many things happened that seemed unimaginable when I was a child. 

You are a musician’s musician. You’ve collaborated with a ton of musicians: Coldplay, The Kinks, John Prine. Is there someone you’ve absolutely loved playing with over the years? 

One of my heroes was Nick Lowe from England. I mean, we had the Elvis Costello albums, which Nick, you know, he produced some of those and he was the first person I ever heard actually cover one of my songs. But we’ve done a bunch of tours together, and you know, we generally will sing a song or two during the encore, and we just have a really, I think, a good sound. I always thought we should have made a record or something together, but we speak the same language musically. We have a lot of the same influences. 

I hear you got to perform with Leonard Cohen. And, if I have this right, in the basement of an Indigo?

He came out with a book, and so the people at Indigo felt would be nice if I came down, you know, there’s going to be this sort of celebration, and you know, the Barenaked Ladies were there.

But when I arrived at the bookstore, they took me down to the basement. As I got off the elevator, I could hear people singing and [was] a bunch of other people all singing with Leonard kind of in a circle. But I was shy about it. So I was sort of hanging back against the wall. And Leonard saw me and he walked over and he put his arm in my arm, and he brought me into the circle, which was one of the nicest things. And someone handed me a guitar.

I have the superpower of remembering lyrics … so I just started playing all these obscure Leonard songs. And Leonard was right beside me. And so when it came time to actually go out on the street, we were playing for about 5,000 people or something. Leonard, you know, he said he didn’t want to sing, but I could tell that he wanted to sing. So when we got up there, you could actually see this on YouTube. We start playing So Long, Marianne, I sing the first verse, and out of the corner of my eye, I see Leonard there. I said to myself, ‘Well, nobody wants to hear me singing a song.’

WATCH | Ron Sexsmith sings with Leonard Cohen

So I whispered the first line into Leonard’s ear, and he got up and sang and everybody went nuts. And so if you see it at the beginning of every verse, I go whisper in his ear because it had been so long since he’d done that. 

Q&A edited for clarity and length. Interview produced by Laurie Allan.