And I once heard a drunk guy sing Irene goodnight in a way that made me wanna die on the barroom floor

But when I turn my radio on and hear them billion dollar songs I wanna die in a different way for sure

— Conor Ryan Hennessy, “If”

I was sitting at the bar at The Midway in Jamaica Plane last month when I first heard that song. I wasn’t feeling great, only there because I was playing after him, but hearing that song and a few others he played gave me a new energy for that night. I’d seen him play a few times before — at parties held by Sonny Jim Clifford of flying circus fame and at the Devlin’s open mic — but that night was when I realized he was probably the best folkie I’ve seen in this town.

Conor’s a humble gentleman, telling me during an interview, “I didn’t realize I don’t like talking about myself.” An engineer by trade, he’s currently working as “a technical writer, which means I technically write.” He struggles to answer simple questions about his art, giving the impression he doesn’t think about what he’s doing, he just does it. When pressed on his influences, he discusses–besides the obvious of Dylan and Guthrie–Big Bill Broonzy, Mississippi John Hurt, and the Irish folk scene of the ‘60s like Lonnie Drew and Luke Kelly. Influences he wears on his sleeve, since he sounds like he’d be right at home in the Greenwich Village folk scene of the 1960s. But no artist is definitively his muse. What really drives his songwriting is “things I’ve noticed or don’t understand about society in general–or a punchline I’ve thought of and write a song about it.”

There’s a duality to his music. While he might write a goofy tune like “Millennial Mesmerism,” a critique of commercial mysticism, he’ll also write a down to earth working class lament like “My People Look Tired.” He describes this duality as a necessity. “I noticed I had to make songs funnier ‘cause — the shows you and I play, sometimes a person will play great songs, but they’re so spirit crushing, you gotta mix it up. Sometimes you can get your point across better if you can get people to laugh,” and tells a story about having to change his setlist playing a song circle at Club Passim because everyone else’s songs were such downers, he needed to be comic relief. He cites as comic inspirations Mitch Hedberg and Norm MacDonald. All his jokes ultimately have a point and pack a punch, such as “If,” where he writes, “Well people think I’m joking when I’m singing/But in between these punchlines there’s a truth.”

Perhaps most surprising about Conor is that, despite his mastery of the written and sung word, literature wasn’t second nature to him. He discussed with me how he didn’t read much until a few years ago, and he feels like he’s still playing catch up. He loves the old Russian writers like Dostoyevsky and Checkov, but he doesn’t profess to be terribly well read. He picked up his poetry chops from listening to old bluesmen and folkies, and it seems that was more than enough to make him a great poet.

When asked where he’s heading, Conor doesn’t indicate any desire to change styles. He’s satisfied with what he’s doing and just wants it to keep improving. He discusses how his early stuff was “based in ballads that are well known or old country-blues songs I really liked. Lately I haven’t been using the crutch of folk music so much. I hope I get more original…I hope I stick at it and get better at it.”

Conor currently has four albums available on his bandcamp and three on Spotify.


Elizabeth von Teig is a musician and author living in Brighton, Massachusetts. Her expertise is classic rock, folk punk, and the blues.