40 Saddest Country Songs of All Time

Cry, Cry, Cry: From George Jones to Brad Paisley, the biggest weepers ever

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31. Townes Van Zandt, "Waiting Around to Die"

"This is the first serious song I ever wrote," Van Zandt told the audience before introducing this somber tune on his 1973 record Live at the Old Quarter. Originally released on 1968's For the Sake of the Song, it's the solemn story of a boozy rambler struggling to see the point of a fruitless existence that precedes eternal silence, ending with this tragic couplet: "His name's Codeine, he's the nicest thing I've seen/Together we're going to wait around and die." It's delicately heartbreaking and eerily prophetic to Van Zandt's early demise at 52 from alcoholism. Still, he was hesitant to play it at concerts since, as he said, "Nobody wants to hear blues on blues on blues." Turns out, they sure do. "That's what music's all about, when you hear something and you don't really have a choice," said Alex Turner of Arctic Monkeys of Van Zandt's work, "but to think, 'Oh fuck, all right, I'm going there.'"

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