The movie features the first known recordings of Grammy award winners Steve Earle and Rodney Crowell who were quite young at the time and appear to be students of mentor Guy Clark.

The filmmaker goes to Austin and visits Townes Van Zandt at his trailer (at what is now 11th and Charlotte in the Clarksville neighborhood of downtown Austin) and his girlfriend Cindy, his dog Geraldine, Rex "Wrecks" Bell, and Uncle Seymour Washington at the home of Washington, who is also called "The Walking Blacksmith," and who gives his great worldly advice to the viewers and represents a very important aspect of the atmosphere that these songwriters living in the South are surrounded by and involved in.

These songs include, "Mercenary Song," "Elijah's Church," and "Darling Commit Me" by Steve Earle, Earle and Crowell covering "Stay a Little Longer" by Bob Wills, "Desperados Waiting for a Train," "Ballad of Laverne and Captain Flint," and "Country Morning Music" by Guy Clark, and "For Ever, For Always, For Certain" and "Hard by the Highway" by Richard Dobson.

Pauline Kael wrote highly of the film and its lyricism, but lamented the loose structure and lack of contextualizing information: Szalapski is an attentive and scrupulous cinematographer; he loves his subjects, and the imagery is so warm and finely detailed that I had a hard time believing I was seeing a blow-up from 16-mm.

[3]Janet Maslin also noted the unfocused ambience: The camera periodically (and somewhat unpredictably) drops in on a tavern where the regulars play pool and grouse about what country music is coming to.

[4]Contemporary critics, such as Doug Freeman, see the lack of structure as a strength: Yet in many ways, Heartworn Highways refuses that historicizing assessment, even resists it.