The intro track to Pain Esquire, the solo debut from Ryan David Roberts, doesn’t sound like a real song. That’s what a friend told him, anyway — and Roberts didn’t accept the suggestion to flesh it out a bit more. In fact, he declined to change it at all. 

“I'm just trying to write the song the way the song needs to be written,” he says.  

That’s generally how the making of Pain Esquire went: Roberts uncompromisingly followed his gut. Tersely punk in length and akin to experimental folk in lyrical delivery, the songs of Pain Esquire are subtly unusual. They’re peppered with invented words, unexpected vocal techniques and metaphors that, to anyone but Roberts, don’t make sense outright. 

But Pain Esquire is no paracosm; it’s not a fantasy world. The EP is a direct reflection of how Roberts’ experiences life. 

“This stuff feels authentic to me. I don't feel like I'm doing one thing or another. It's just kind of what felt right or what sounded right at the time,” Roberts says.

Originally from Atlanta, Roberts then relocated to NYC for about a decade. Since 2014, however, he’s lived on the outskirts of Winnipeg. A lifelong band player, it’s because he was — at the time — somewhat disconnected from collaborative possibilities that he moved forward alone, save for the help from producer Adam Fuhr of House of Wonders. 

It was a formative shift. Roberts now knows the satisfaction of music-making directed solely by his own intuition. 

The EP’s most straightforward listen is “Really Won’t Come Back,” a melodically catching study of loss and grief in both past and present tense. “Reaper” too is an earworm, and this time, Roberts offers a comprehensive narrative. 

Elsewhere, Roberts is less accommodating. However, despite his embrace of the off-kilter, rather than the traditional,  the rest of Pain Esquire is also affecting. These tracks are compelling, yet puzzling. They resonate — and it’s up to the listener to figure out why. 

The ‘60s experimentations of poets Amiri Baraka and Bob Kaufman run deep in Roberts’ influences for Pain Esquire. Modern-day artist R.A.P. Ferreira is in there, too. Amid the seriousness and sincerity of their work, there is a sense of humor. Roberts operates similarly. 

Some of Pain Esquire was long-clogged in the songwriting pipelines. It didn’t fit with his previous bands, wherein strategic packaging regularly shifted downtrodden songs into happier moods. This time, the necessary compromise of creating in collaboration isn’t a factor. 

Roberts leaned into himself fully on Pain Esquire. He confronts his own contradictions, lays wide open his laments and regrets. There’s hope though, too.  

Pain Esquire is a mollusk without a shell. It may feel a little strange at first, to see it so exposed. But the closer you look, the more interesting it becomes.

04 REAPER

Ryan David Roberts

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