40 Saddest Country Songs of All Time
Cry, Cry, Cry: From George Jones to Brad Paisley, the biggest weepers ever


GAB Archive/Redferns/Getty Images; Mark Humphrey; Michael Ochs Archives/Getty Images
From the hillbilly music of the 1920s and the honky-tonk of the Forties and Fifties, to the Bakersfield movement of the Sixties and the Outlaw country of the Seventies, country music has always done a fine job of breaking our hearts. It’s a trend that continues well into today, even as the genre gets glossier and incorporates new sounds. These are the 40 saddest country songs ever written — each of them an entry that will put a tear in your beer.Â
Editor’s note: a version of this list was originally published in 2014.