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 ...

Why do we enjoy songs that make us cry? It seems like the more heartbreaking the song, the more we love it. Even if a song could win the prize for Most Annoying Musical Endeavor Ever, (“Having My Baby ...

Is Christmas really the saddest day of the year? There’s a whole history of holiday music that explores what it’s like to be down-and-out during the season. Are you mourning absent family members?

Need a good cry? In the mood to revel in your own misery? There are plenty of songs that make such an experience even worse! Though, we won’t judge you for indulging in a few heartbreaking songs if ...

The 2020s may only be halfway over, but already, this decade has produced a bumper crop of heartbreak songs and tear-jerkers. Some artists opened up about their mental health struggles and childhood ...

In honor of National Grief Awareness Day on Aug. 30, I listened to some of the saddest songs ever written and recorded, trying to pick out the saddest ones of all. I’ve experienced my own share of ...

The list of country songs with heartbreaking lyrics could go on for days. There are plenty of sad songs with lines that push them over the top. Then, there are songs that seem like sweet love songs in ...