Playing to the converted is easy, as is building a fan base on the back of a smash radio hit or prime soundtrack placement in a popular TV show. Winning over crowds through good old-fashioned sweat and charisma is, however, a considerably more daunting task.

Reached at a tour stop in North Dakota, Hamilton-born, Halifax-based singer Ben Caplan professes to be more than up to the job of rolling into a town cold and then making the curious feel like they’ve just discovered their new favourite artist. Part of the appeal is borderline-theatrical songs that put the freak back into junkyard-blues folk. It probably doesn’t hurt, either, that Caplan sports the kind of beards-gone-wild facial hair that would impress Sam Beam, William Fitzsimmons, and Rick Rubin. Based on his appearance alone, he’s impossible to ignore.

“In Canada, we’ve been doing well over the last couple of years, so we show up pretty much anywhere we go and we’ve got some people who are pretty excited to see us,” Caplan says, speaking on his cell. “Last night in North Dakota, I’d never been to that part of the States before, so I had the vibe by song two or three that no one had any idea what to expect. It was like, ‘Everyone’s here to see a show, not necessarily my show.’ By the end of it they were just thrilled. Afterwards, I was doing some signing at the merch table and hanging out with the crowd and people told me they were just flabbergasted. It was great to see people who had no idea who we were and what we were about come away from it as hard-core fans.”

What the singer and showman is all about on his second full-length, Birds With Broken Wings, is excess, which we mean as the highest of compliments. Although Caplan plays live with a stripped-down cast of hired guns called the Casual Smokers, the record features contributions from 27 backing musicians, with everything from cellos and violas to darbukas and cimbaloms thrown into the mix. The result is everything from Gypsy ragtime (“Birds With Broken Wings”) to dive-bar country (“Belly of the Worm”) to nicotine-yellowed jazz (“Deliver Me”). Through it all, Caplan sings like a man raised in skid-row diners on cheap gin and filterless cigarettes.

Often beautiful despite its rough edges, Birds With Broken Wings wasn’t an effortless affair.

“I was hoping this record would be a two- or three-week project, and then it turned into a nine-month project,” Caplan says. “It took a long time to make, and probably cost double what I intended to spend. But once I got into it I felt the need to keep doubling down. I felt that the songs had so much potential, and the project had potential that, when we ran out of money and I had new ideas on how to refine things, I just went and found some more.”

Despite its audacity, Birds With Broken Wings is a record with a serious message, even if the songs are often left purposefully open-ended. Lines like “I have seen with my eyes images I wish I could erase,” from “40 Days & 40 Nights”, are powerful, but it’s up to the listener to decide what Caplan is singing about.

“My mind is often in different spots in each song, but if I could generalize I’d say I’ve spent the past few years meditating on what is going wrong in the world,” he offers. “I believe strongly in looking for social justice, searching for environmental justice, and trying to live in a just world while creating a just society.”

That doesn’t mean, however, that he’s not up for having a blast on-stage, especially on nights when he’s got the element of surprise working in his favour.

“We’ve been on the road now for quite a few weeks,” Caplan says. “As a band, we’ve been playing together for a few years, and we put a lot of work into this record, so we’ve got a pretty tight ship. The sound on-stage and in the room is the best it’s ever been in my career. Some people in places like North Dakota come to the show expecting a mid-level band playing some songs. But we really put on a performance. I hope it doesn’t sound egotistical to say so, but people tell us that we really kill.”

Ben Caplan and the Casual Smokers play the Biltmore Cabaret on Monday (October 26).