When asked why all his songs were sad, Texas troubadour Townes Van Zandt replied, "They're not all sad; some of them are hopeless." That was in 1995, two years before his death.

Van Zandt did not lead a happy life. Born of a rich family, he jumped off a fourth-floor balcony in his mid-20s "just to see what it would feel like." His parents then shunted him off to an asylum for insulin shock treatments. When he got out, he hitchhiked all over the country, writing songs and playing dead-end rooms before holing up in a Tennessee cabin without electricity or running water for much of the '70s. He got drunk, got sober, got strung out, got married, got divorced, got drunk, and so on.

And why should you care? Well, because Townes Van Zandt wrote and sang some of the most heartbreakingly beautiful songs you've ever—or never—heard. Maybe it's the crack in his voice, or his wry gallows humor, or maybe it's an unnamable something that makes you want to jump off a fourth-floor balcony with the man. Just to see what it feels like.

Van Zandt's recordings are uneven, as might be expected from someone who led such a troubled life. But in 1973, in a series of shows at the 60-person-capacity Old Quarter in Houston, Van Zandt seems to have had a few moments of clarity. The magnificent double CD Live at the Old Quarter was patched together out of the best of those moments.

"Pancho and Lefty" opens the show, Van Zandt's arid voice and spare picking giving the song a spectral feel. Although he was little known during his life, his songs have been covered by the likes of Steve Earle (who proclaimed Van Zandt a better songwriter than Dylan), the Cowboy Junkies, the Walkabouts, Emmylou Harris, and Willie Nelson, who made "Pancho and Lefty" famous. In these Old Quarter shows, Van Zandt stands alone onstage, backed only by his acoustic guitar. The sound is warm and intimate, as though he were playing for his closest friends. Other standout tracks include the poker ballad "Mr. Mudd and Mr. Gold," the stubbornly hopeful "If I Needed You," and the stark, bitter "Waitin' Round to Die," the first song Van Zandt ever wrote.

Tragically, the album has been in and out of print, so you may have to dig a while to find it. Other worthy introductions to his plaintive, lonesome work are his first, self-titled album, and the follow-up, Our Mother the Mountain. But dig a bit for this one first; it's worth it.