Hmm, the thing about Van Zandt's music is that, for me, it hasn't really dated. His best songs already seem timeless. Most of the studio albums are dated, but that's mainly due to questionable production values.
Whenever people ask me what I think the saddest song ever is, I have to tell them that it's the version of Tecumseh Valley on Rear View Mirror. Owen Cody's fiddle playing is one of the most stunningly haunting instrumental performances I've ever heard.
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