5 Stellar Heartbreak Songs From Townes Van Zandt

It’s difficult to imagine the modern Americana ballad without the examples provided time and again by the legendary Townes Van Zandt. The Texan combined his knack for poetic eloquence with lived-in realism to offer some of the best sad slow ones ever released.

If you’re looking to wallow a bit over love gone wrong, choosing Van Zandt as your delivery system will never lead you wrong. Here are five of his best, to use one of his own phrases, lonesome tunes.

“Fare Thee Well, Miss Carousel” from Townes Van Zandt (1969)

The best Townes Van Zandt album? We’d have to go with his self-titled third release, which arrived in 1969. Van Zandt rerecorded four songs that had been released on his debut album For the Sake of the Song, one he thought was failed by overbaked production. He also was at the top of the game in the new songs he penned, with “Fare Thee Well, Miss Carousel” standing out as a particularly impressive flex. The length (six verbose verses) and the narrator’s combination of admiration and frustration for the title character is somewhat reminiscent of Dylan. But Van Zandt’s wondrous wordplay is all his own.

“None but the Rain” from Townes Van Zandt (1969)

There are certain Van Zandt songs where just the title alone is a pretty good indication you’re in for something special. “None but the Rain” immediately hints at a sad farewell before you’ve even heard a note. He doesn’t get enough credit for the beauty of melodies such as this one, which gets a boost from the subtle woodwinds added to the track. Van Zandt had a knack for writing songs like this, where the separation is already a foregone conclusion. The important thing is the aftermath, and how the parties involved can ever possibly move forward without breaking completely.

“Only Him or Me” from Delta Momma Blues (1971)

Van Zandt’s recording career was a series of varied experiments, in terms of the types of backing, the people with whom he worked, and the production strategies. For the 1971 album Delta Momma Blues, he tried working in New York City. But no matter what surrounded him, it was impossible for any circumstances to diminish the brilliance of songs like “Only Him or Me.” Here he’s singing to console someone he’s about to leave behind. Underneath that, there’s also a sense of sadness that emanates from the narrator’s own subtle resignation he might never find another like her.

“Tower Song” from Delta Momma Blues (1971)

The sorrowful part of this song from Delta Momma Blues is there should be some hope for the relationship at the heart of it. But the girl that the narrator’s beseeching refuses to fight for it, lest she feel the pain that could be forthcoming. At this point, he’s caught somewhere between making one last plea and simply giving up. Sadly, by song’s end, we know how he’s chosen: The end is coming soon, it’s plain. Sadder still, he likely will be long gone by the time her defensive tower finally does come crashing down, if it ever does.

“Catfish Song” from At My Window (1987)

Van Zandt’s personal demons, coupled with an industry that didn’t quite know what to do with his songwriting genius, caused him to record sporadically over the last few decades of his life. In 1987, he released At My Window, his first new studio album in a nine-year stretch. The wear and tear on his vocals, compared to his previous outing, was noticeable. But that weathered vibe only played into the regretful tone of the lovely, heartbreaking “The Catfish Song.” Van Zandt sings of his wasted youth from the perspective of someone who knows his romantic mistakes but can’t go back to correct them.

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Photo by Frans Schellekens/Redferns