Heartworn Highways: A Reckoning with the Soul of Outlaw Country

By Danny Gonzalez | April 22, 2025
Heartworn Highways: A Reckoning with the Soul of Outlaw Country

 

Released in 1976, Heartworn Highways offers an intimate portrait of the American singer-songwriter scene at a pivotal moment in the history of country music. Directed by James Szalapski, this gritty and honest documentary drifts the way its characters do – free, like outlaws.

Heartworn Highways utilizes a freeform style that allows the music that would come to be known as “outlaw country” and the rare performances its camera captures to unfold organically. At the heart of the film is a sense of rebellion, authenticity, and emotion. You see performers like Townes Van Zandt, Guy Clark, Steve Young, and Charlie Daniels – songwriters who bled into their music, not for fame or for money, but because that’s who they were. Szalapski captures them in their element, allowing these artists and their environment to speak for themselves.

The film transitions naturally from moments of quiet intimacy to ones filled with the energy of a live performance. We watch as Steve Young plays a song with an intensity that feels spontaneous, and a moment later we’re back at a quiet gathering, sharing a drink and a song with the artists in their homes.

At the end of the day, Heartworn Highways is all about the music. The songs performed in the film are steeped in the American experience. From quiet front-porch singalongs to rowdy nights where music is the only thing holding people together, Heartworn Highways doesn’t separate the art from the artist. It shows it all. Every note and every lyric matters. Songs about love, loss, and trying to make peace with a life that never quite made sense – you’ll hear it all, and if you’ve ever lost something or someone, you’ll feel it too.

The film documents a scene that was both rebellious and introspective. It shines a light on the artistic and creative process of these iconic musicians. By focusing on their lives and their music in such an intimate and personal way, the film allows us to appreciate the essence of their work.

Why You Should Watch Heartworn Highways

Heartworn Highways is a rare, unfiltered look into the world of outlaw country and folk music at its peak. This documentary isn’t just about the artists it features, but also the spirit of a time and place that doesn’t exist anymore. 

For anyone interested in understanding the roots of modern Americana and alt-country, Heartworn Highways is an honest, soulful tribute to musicians whose influence can still be felt today. This documentary is a love letter, but not the kind you write. The kind you live. And once you’ve seen it, it doesn't leave you.

Heartworn Highways is returning to theaters for select screenings nationwide in celebration of its 50th anniversary and is also available to stream on Kino Film Collection.