These three country songs, all released in 1989, are among the saddest country songs that have ever been released.

The 2000s delivered some of country music's stone-cold saddest songs, ever. Want proof? Brad Paisley and Alison Krauss' "Whiskey Lullaby" — one of country music's defining heartbreak ballads, and a ...

We’re starting our list of somber ’00s country songs with Rascal Flatts’ “Skin (Sarabeth).” This ballad about childhood cancer is almost too much to bear. Reading the lyrics alone is enough to start ...

The 1990s just might be the definitive era of sad country music. For starters, some of the genre's all-time best storytellers and vocalists were at the top of their game during this period. Acts like ...