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. 

Editor’s note: a version of this list was originally published in 2014.