Ron Sexsmith’s Memorable Encounters: From Massey Hall to a Basement with Leonard Cohen

As Canadian singer-songwriter Ron Sexsmith celebrates his 60th birthday, he reflects on his storied career and the diverse collaborations that have shaped his musical journey. From headlining iconic venues like Massey Hall to impromptu performances with legends like Leonard Cohen, Sexsmith’s anecdotes offer a glimpse into the rich tapestry of his experiences.

Sexsmith’s upcoming concert at Massey Hall holds special significance, not only as a milestone celebration but also as a nod to his longstanding admiration for fellow Canadian musician Gordon Lightfoot. Reflecting on his humble beginnings as a courier listening to Lightfoot’s performances from the venue’s stage door, Sexsmith acknowledges the profound impact Massey Hall has had on his career trajectory.

In conversation, Sexsmith delves into the introspection that comes with reaching the age of 60, noting his initial apprehension about the milestone and his eventual embrace of it. He shares insights into his decision to commemorate the occasion with a retrospective concert, highlighting the significance of reuniting with his band for the first time since 2018.

Acknowledging his role in the Canadian songbook, Sexsmith humbly reflects on his contributions to the music landscape. Despite accolades from enthusiasts and critics alike, he remains modest about his place in the canon of Canadian songwriters, emphasizing his dedication to crafting meaningful music and building a diverse body of work.

Among the highlights of Sexsmith’s career are his collaborations with esteemed musicians like Nick Lowe, Coldplay, The Kinks, and John Prine. However, one particular moment stands out: a serendipitous encounter with Leonard Cohen in the basement of an Indigo bookstore.

Recalling the intimate gathering where Cohen invited him to join a circle of musicians, Sexsmith recounts the surreal experience of performing alongside the legendary songwriter. From singing obscure Leonard Cohen songs to sharing the stage with him in front of thousands, Sexsmith cherishes the memory as a testament to Cohen’s generosity and camaraderie.

Embedded within the narrative is a video capturing the magic of that moment, a poignant reminder of the profound connections forged through music. As Sexsmith continues to navigate his musical journey, his encounters with icons like Cohen serve as enduring reminders of the transformative power of song.