This came out in 2003 – or at least that’s when I got it. Here’s what I said about it back then (with some minor editing):
Townes Van Zandt. Guy Clark. Rodney Crowell. John Hiatt. If these legendary singer-songwriters mean anything to you, Heartworn Highways is a film that will very likely mean a lot to you.
This intimate 80-minute documentary was shot back in 1975, and captures the maverick troubadours above (and plenty more) as they play, sing, work, party — and, in the process, reinvent country and roots music for the post-hippie generation. Heartworn Highways isn’t perfect — there’s a lot of skippable footage of amateur-hour roadhouse shows and forgotten pickers like Larry Jon Wilson and Gamble Rogers. But there’s more than enough amazingly cool footage to make up for it — like Van Zandt singing Waitin’ Around To Die in his kitchen (and wandering around his backyard with a bottle and an air rifle), David Allen Coe performing in prison, and a drunken Christmas Eve jam around Clark’s dining room table. Even cooler: Nearly an hour of extra footage that didn’t make the initial cut, including a bunch of tunes sung by some skinny-assed, 20-year-old nobody named Steve Earle. Essential for roots fans.