‘Sexsmith at Sixty’: The singer-songwriter has never had a top 40 hit, but he’s earned the admiration of some of the biggest names in the music business.

by Nick Krewen

Special to the Star

Even Ron Sexsmith would admit he’s a bit of an anomaly.

On Thursday, as he performs his career retrospective “Sexsmith at Sixty” while headlining Massey Hall for the sixth time, it’s worth noting that the mellifluously voiced St. Catharines-born singer/songwriter has overcome seemingly insurmountable odds to prosper in this complicated profession known as the music business.

For instance, although his sweetly melodic and life-profound fan favourites, like “Secret Heart,” “Strawberry Blonde” and “Gold in Them Hills,” usually clock in under four minutes, he rarely gets any radio airplay and has never had a Top 40 hit.

And while he’s churned out 17 albums for various record companies since releasing his self-titled non-independent debut in 1995, Sexsmith has never come close to selling the oodles of long-players such corporations ultimately desire of their signings.

But he has won the admiration of his peers, with some of the biggest, most respected superstars in the business publicly offering their acclaim: Paul McCartney, Elton John, Bob Dylan, Elvis Costello, Paul Simon, Ray Davies, Steve Earle, Pete Townshend, Chris Martin … not only does the list go on, many of them have worked with him, either as special onstage guests or in the studio.

And many more have covered his songs: Michael Bublé, Rod Stewart, k.d. lang, Emmylou Harris, Feist and Lucinda Williams.

Those endorsements have built Sexsmith a fandom that has enabled him to tour the world and amass a Spotify following that currently sits at 142,000 monthly listeners.

Sexsmith, who was weaned largely on British pop and rock, is grateful for the high profile support of some of the artists he’d always fantasized about meeting but never thought he would.

“I’ve been really fortunate to have met some of my biggest heroes,” he said during an early February phone interview. “Ray Davies, for one: I sang with him a couple times. I worked with him at the studio one day, at Konk Studios in London: that was just surreal.

“Obviously, there’s the famous Paul McCartney story and that was a pinch-me moment, where I got to have breakfast with him and we jammed a little bit. And Elton John’s been very nice to me: we went to see him on the first round of the Farewell Yellow Brick Road tour and he gave me a shout-out and brought us backstage to see him after. 

“It’s crazy — I was a kid with my wall-to-wall Elton John posters in my bedroom and a member of his fan club. So all of these have been really unexpected highlights.”

His biggest highlight?

“That I actually got in the door,” Sexsmith said.

“I was pushing 30 when I got my record deal and there were many people in my life telling me to pack it in, you know?         

“Because I had kids, people said, ‘Maybe you should get a job at the post office or something.’ I’m just really glad I hung in there and I’m still sort of hanging in there.”

The secret of his success can be attributed in small part to manifesting his own destiny.

“It might be a cliché but, like most people who set out to do this, I was a dreamer,” Sexsmith explained. “Since I was nine or 10, I was thinking, ‘This is what I want to do.’ I wanted to write songs and make records. Well, actually, at first I just wanted to sing.

“So it’s amazing; it’s like you send this desire out to the universe and, if you never stray from that, all of a sudden the door opens and it kind of happened for me.

“And I was just so grateful. I really felt like it was meant to be. And I can’t believe where it’s taken me: I had never been on a plane before I had my record deal and now I’m playing all over the world, and I have this body of work that I’m really proud of.”

The former courier has more than earned his flowers as a type of songwriting preservationist, which is why he has attracted adoration from so many famous song architects.

“I think these guys recognized that I have so much respect for what they did and that I was trying to follow in their footsteps,” Sexsmith said. “Randy Newman once said he liked my stuff because I do the work and that was the biggest compliment because I do do the work: I think about it; I pull my hair out over the lyrics and the structure of the song and all that kind of stuff.

“It’s just amazing that they’ve heard of me and they know who I am, really. When I was at Paul McCartney’s house, we played some songs and I was too afraid to play him one of mine, so I played him one of his. I mean, these guys wrote the book and I’ve just been a really good student.”

Yet, Sexsmith is concerned that his methodology might be fading from practice, losing ground to committee-driven studio production techniques.

“Maybe that’s how it should be,” he reasoned. “A few years ago, I was watching the Junos and looking at the songwriter category, and pretty much every nominee for song of the year was written by about six people.

“I’m kind of a purist. I don’t really co-write for my own albums. I used to love to look on the back of an album where it would say, ‘all songs written by Gordon Lightfoot,’ or a songwriting team like Elton and Bernie (Taupin).

“I feel there’s a lot of affectation these days: it sort of supersedes actual melody. (Artists) just do something with their voice over whatever the track is and that’s a song.

“But I try to write songs that can exist whether I’m singing them or not. They have a really definite melody and a structure, and you can change the key. You can take a Hank Williams song and add jazz chords to it, but it’s still a Hank Williams song, right?

“So that’s where I’m coming from. I don’t know if a lot of the newer songwriters are coming from the same place or not.”

His relocation from Toronto to Stratford with his wife, Colleen, played an important role in his last two efforts, 2020’s Hermitage and 2023’s The Vivian Line.

“I think they are very reflective of this new life I have in Stratford,” he said. “There’s a feeling of peace. I walk around the river downtown and there’s swans and everything, whereas in Toronto I was dodging cars and carrying coffee around. It was the stress of surviving.

“I think Colleen and I have found ourselves in this new situation that’s been very inspiring.”

Although his upcoming “Sexsmith at Sixty” date suggests a birthday celebration, the singer says he had a completely different motive in mind for the show.

“I wanted to do this show because I’m proud of the contribution that I’ve made to the Canadian songbook,” he said. “But I don’t always feel that it’s valued here in my own country. So I just really wanted to do something to say, ‘Hey, everybody, I’m here, this is what I’ve been up to for all these years,’ and just stand up for myself, really.

“That’s what the concert is about … not celebrating my birthday, because I wasn’t happy about turning 60.”

And for this one-off show — which will consist of two full sets with intermission — Sexsmith said Massey Hall was the only venue he considered.

“Originally, Massey Hall was a lifelong dream just to play there,” he said. “When I was a courier, I used to walk by Massey Hall all the time and I felt like I was stalking it: ‘I’m going to get in there one of these days.’

“And I think about a time when I used to go there for concerts. I couldn’t afford to get in and I’d listen to the whole show by the stage door, and then wait for them to come out and maybe get their autograph or something.

“Anyway, I’ve headlined Royal Albert Hall, which is one of the top venues in the world. But Massey Hall even tops that for me.

“If I did have a birthday wish, yeah, I would love to fill Massey Hall. I don’t know if that’s realistic, but I’ve put that out to the universe to see how it flies.”