Listers have put out dark country music, but No. 1 on this list is a deep cut you might have never heard before.

Some of the best sad music comes from 90s country songs. Sometimes we can all use a good cry to let out our emotions. And what better way than listening to some songs that make you cry? Take yourself ...

I know what you're thinking: Every Radiohead song is sad. Well you're wrong! Data scientist Charlie Thompson has mapped out every Radiohead song by how sad each song sounds (and how sad the lyrics are ...

It's totally normal to need a good cry sometimes, and there's nothing that does the trick quite like the best sad songs can. Hearing your favorite artists of all time singing the saddest lyrics and ...

Are we intentionally making ourselves feel worse by listening to sad music? Studies show that the reason we always go back to ...

Don’t believe the hype: Love stinks, and no day reminds you of its follies quite like Valentine’s Day, as marketers fall over themselves to remind you you’re really on your own. To make the occasion, ...

Country music star Chris Stapleton is known for writing some real tear-jerkers. These three songs aren’t the only heartbreaking tunes that Stapleton has penned and produced, but they’re three songs ...

Heartbreak was already a big country music trend by the time the 1970s rolled around: Check out this gallery of great '60s sad songs for proof. But with a new decade came along a whole new crop of ...

This song from Swift's debut album first introduced us to her incredible songwriting. The comparison of a cold-hearted person to the cold, dreary weather will absolutely give you chills every single ...

One of the 1990s’ most prolific singer-songwriters was celebrated for their emotional, raw, and deeply personal storytelling. It’s no surprise, then, that their saddest song has become a viral ...

“Goodbye May Seem Forever” would be higher if The Fox and the Hound was a better movie. Overall, it’s mediocre, but this song hits the emotional target. After Amos Slade threatens to kill Tod, Widow ...

Delirium is a really upbeat album, and it’s seemingly different from your previous records. Is there a misconception of you not being happy in your older songs? I think they’re right. Lights was a ...