Listen to this track by St. Catharines Ontario favourite son and effortlessly awesome singer-songwriter Ron Sexsmith, with his former collective known as The Uncool – Steve Charles on bass, and Don Kerr on drums and backing vocals. It’s “Don’t Mind Losing”, a jubilant Moondance-era Van The Man style acoustic soul-pop gem as taken from his 1991 independently released album Grand Opera Lane.

The song, and the album off of which it comes exists as something of a prequel to his major label debut Ron Sexsmith in 1995. You can hear the decidedly different tone and approach to presentation and style characterized by more overt soul and rockabilly references.

Ron Sexsmith had spent some time living in rural Quebec, letting his dream of becoming a songwriter steep while mapping out how he was going to pay for his life in the meantime. While working out how to bring his talent to the table of the music industry, he had a wife and newborn son in tow, with a daughter soon to join them by the end of the 1980s. So, in returning to St Catharines, and then to Toronto, he had to secure a day job as a courier, wondering if his real calling as a songwriter and musician would ever really come to fruition.

It’s a pretty common tale, many versions of which we’ll never get to hear from songwriters who never found their path.

With that in mind, never has a song about feeling set upon by circumstance and existential despair sounded so bright and bouncy, gleaming with horns, a seriously groovy bassline, and ecstatic backing vocals.  But, in all of that aural joy, where does it connect with where Sexsmith was going as a professional musician?

While working full-time, and maintaining family life as best he could, Sexsmith became involved in the vibrant open-stage community in Toronto, including Fat Albert’s where I myself attended shows in the early ’90s when I was a student, since they were free and I had no money. On hand on that scene was Bob Wiseman, who also was the keyboardist for major label outfit and Alt-Country forseers Blue Rodeo, and with whom Sexsmith would work on sessions for a record.

Illustration: John Gushue Dot Dot Dot (click to read his post)

At this point in the early ’90s before the age of streaming and the Internet, the way indie musicians got their music out other than through rigourous live playing, was in the production of cheaply made cassettes that were distributed on a sort of guerrilla marketing level. International chart botherers Barenaked Ladies who came out of similar origins in Toronto began in this very vein around that same time, with their celebrated “yellow tape” EP. Grand Opera Lane was Sexsmith’s answer to that strategy.

In working with Bob Wiseman who served as producer, and in having Blue Rodeo singer, guitarist, and songwriter Greg Keelor as a guest on one song (“Gonna Get What’s Mine”), it was hoped that the record would gain the attention of the majors. But, it wouldn’t happen – at least not with Grand Opera Lane. Even if wider recognition would be delayed, Sexsmith would still proceed to reveal his talent for compelling lyrical ideas and catchy melodies on this album. And “Don’t Mind Losing” is a prime example.

The song’s lyrics are decidedly downbeat. Yet, the music is defiantly contrary, a party tune with sadness and frustration hidden away behind a smile. It’s no wonder Elvis Costello, among others, would become a fan. And even if Sexsmith was working in a more straight-ahead rock ‘n’ roll vein on this song, and on many of the other songs on the album, songs like “Trains”, and of course an early version of “Speaking With the Angel” would point in the direction that was calling him to become recognized as one of the most gifted songwriters our country has yet produced.

For more information about this song and the other songs on the album, check out the excellent short sleeve notes on Grand Opera Lane, written by Ron Sexsmith himself.

And just as we wished David Bowie a happy birthday this past January 8th, we wish the same for Ron, who was also born on that date (along with Elvis Presley, no less).

Enjoy!

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