40 Saddest Country Songs of All Time

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

9

Lefty Frizzell, "Long Black Veil"

Recorded during the dawn of the highly stylized Nashville Sound era, "Long Black Veil" was a musical departure for honky-tonk singer Lefty Frizzell. Amid a weeping slide guitar and soft, shuffling rhythms, Frizzell tells the tale of a man falsely accused of murder: Our hero can't provide an alibi — to do so would expose the affair he had been having with his best friend's wife — so he ends up executed for the crime, literally taking his secret to the grave. The saddest moment, however, is reserved for his lover, wailing under cover of the night winds. "Nobody knows but me," Frizzell sadly sings with his deep, gentle twang. "The Long Black Veil" was written by Danny Dill and Marijohn Wilkin, who say part of the inspiration for the song was based on a mysterious veiled woman who often visited the grave of Rudolph Valentino. 

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