Any fan of John Prine is a friend of mine.

That means, then, that Ed Romanoff and I could be good buddies. I count Prine as my all time favorite songwriter. Years ago, Prine’s work inspired Romanoff to learn to play the guitar, and it was Prine’s depressingly romantic “Hello In There” that he counts as the first song he mastered.

A listening party might be in the offing.

This month, the award winning Romanoff is releasing his second record, The Orphan King, as the follow up to his critically lauded 2012 eponymous debut.

Romanoff’s work reminds me a lot of Prine’s; somber and contemplative, rich with insight and introspection. The new record features a bevy of guests, including famed guitarist Larry Campbell, who has worked with Bob Dylan and The Band, and was produced by Simone Felice.

I recently caught up with Romanoff to chat about the new record, odd jobs, and our shared love of the singing mailman.

BRO – You are celebrating the release of your second record. Which one was the bigger challenge? This one or the first one?

ER – I think this one was a little more fun because I’d done it once before. The first record was something I never thought I’d live to see, so that seemed like a pretty tall mountain to climb. That said, I really wanted to top what we’d done and that challenge was always at the front of my mind for this one.

BRO – Your working life outside of music has included some interesting trades. What job might our readers be most surprised to hear that you have done?

ER – Baking Teflon onto pots in a factory in New Haven, staking hundreds of toilet bowls in Winston-Salem, or jackhammering a shuffleboard court on a ranch in Wyoming. Which do you think is weirdest?

BRO – I am a longtime fan of Simone Felice’s work. How did he influence the crafting of this record?

ER – Oh, man. Simone is a sly genius. He created a dark and magical space to record everything live and he was very open to all ideas. He was particularly great at capturing our vocal takes, and also the song doctoring. Plus, he knew Larry Campbell. Everything got better with his help.

BRO – We are featuring “Less Broken Now” on this month’s Trail Mix. What’s the story behind the song?

ER – Having gone through a pretty debilitating depression after learning my father wasn’t my father, through a DNA test, in 2010, I also got dinged in a few relationships. After that, I finally rediscovered my footing and met somebody new. So, it kind of sums up leaving a sad chapter behind and moving forward with a little bit of grace.

BRO – I read that it was a John Prine record that inspired you to learn the guitar. If you could meet a character from one of his songs, which one would it be?

ER – Just one? That’s tough. Either Sabu, the elephant boy, or the wise poet in “Bruised Orange (Chain of Sorrow), who knows how brutal the world can be, but even so, reminds us that anger is a useless prison.

For the record, I think that stacking toilet bowls is the weirdest of those jobs listed above. Thankfully, it’s a guitar in Ed’s hands now, and not potties, and you can catch him at Rockwood Music Hall in NYC next weekend.

For more information on Ed Romanoff, his touring schedule, or how you can get a copy of his new record, check out his website.

And be sure to listen to “Less Broken Now,” along with new tracks from Wild Child, Lowpines, and Jim White on this month’s Trail Mix.