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 ...

These sad country songs are stone-cold classics. In the 1960s, heartbreak looked a little different than it does today: There were no breakups over text or email, no obsessively scrolling through your ...

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 ...

Raise your hand if you often find yourself in need of a good cry. Okay, all of us? Now raise it even higher if you like to lean into those feelings by throwing on a masterfully crafted playlist full ...