Seegers isn’t sold on his initial commercial success. Not by a longshot. But he also can’t deny the strides he made in carving out the career he had sought for decades. He doesn’t depend on panhandling for money anymore: he earned a cool six-figure sum, before expenses, in 2014. That’s more than he’s seen in years. Perhaps ever.

The overseas success hasn’t translated back at home. In early October, he released “Going Down to the River” domestically on Rounder Records. The record has sold nearly 6,000 copies in the United States and Canada. He admits that American audiences have presented more of a “rocky road” than Sweden. Lamb thinks the domestic response has moved in the right direction. She points to positive coverage from Rolling Stone, National Public Radio and other national outlets. Gershon isn’t phased by the early numbers, considering how much time Seegers spent touring in Sweden compared to the states.

“Everybody expects this to be a slow build,” Gershon says. “People just don't know about him yet. He's a word-of-mouth artist. And it just really hasn't been here that long to get it out yet.”

Seegers’ biggest challenge remains in Nashville, a city that bills itself as the home of country music, but where writers of traditional country songs now struggle to reach a wider audience. Like many talented local songwriters, the 63-year-old artist faces a tough predicament: How do you land a traditional country song on mainstream country radio? In a perfect world, Seegers would contend for airtime. You’d be hard-pressed right now to find someone who writes with more authenticity than Seegers. And you must be doing something right if your songs are receiving regular comparisons to the Singing Kid.

“He’s too country for country radio,” Gershon says. “Hank Williams today wouldn't get played on country radio. ... It's just semantics: He's a country singer, but he's not mainstream country.”

You can’t dismiss the semantics at this point. They’re forcing Seegers to look elsewhere — folk and festival circuits — for more work. None of that, of course, really matters to the Music Row execs who control the airwaves these days. Beer-guzzling anthems take priority over redemption songs from a man who’s kicked the bottle. In fact, mainstream country has embraced drinking songs so much, arguably more than ever, that it prompted one Billboard writer earlier this year to ask the question: “Does country music need an alcohol intervention?” Maybe mainstream country can someday get back on track. For now, though, it needs a cab ride home.

Yet Seegers can’t abandon the country road that led him to Sweden. That’s why he’ll make a duets record with Johnson sometime early next year. The record, marking their first true collaboration, will likely lead to another Swedish tour next year. Johnson says she’s excited to make a “real” country record for the first time in her lengthy career. Seeger is just as excited

“It will be a real meeting with a real country dude,” Johnson says. “Really mature, deep, soulful country.”

Seegers ultimately hopes he can move past his personal and professional struggles to make further inroads with American country fans. He recently finished a short tour opening for Texas country singer Clint Black, who, granted, is playing in much smaller towns than he did during his platinum-selling days 25 years ago, and has received year-end accolades from NPR Music and the Philadelphia Inquirer.

This Friday night, Dec. 19, he’ll make his Grand Ole Opry debut at the Ryman Auditorium. It’s a short performance, two songs at most, between more established artists. But it’s a major chance for a couple thousand country fans finally to hear his songs in person. Depending on the turnout, the single crowd could very well be larger than the total number of people who ever watched him play outside Goodwill.

It’s not hard to see why Seegers’ “Cinderella story” resonates with a growing numbers of supporters. How can you root against a 63-year-old man who has finally started to fulfill his lifelong country dreams? I couldn’t. But after spending a weekend with Seegers, one thing became apparent: He hasn’t found complete freedom through his recent success, at least not by conventional Nashville standards. He acknowledges his newfound financial security. He’s also grateful to have a stable music career. But if it all came to an end, he would gladly return to busking.

“My biggest joy right now is going out playing on the streets,” he says.

That statement initially surprised me. Most country artists will do anything to perform onstage instead of on the streets. But then again, Seegers is unlike other artists. The arduous path he’s traveled has given him an unique outlook on his music, his hometown, and his life. From where he stands, Nashville’s skyline looks different than it does to the rest of us.