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 ...

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 ...

Each year I’m devastated anew by Vince Guaraldi’s maudlin piano plinking softly under the opening line of “A Charlie Brown ...

Each one of country music's 50 saddest songs is unique, but they all have one important thing in common: They all tell a powerful, tear-jerking story. Some of those stories are on topics that don't ...

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 ...

Amy Winehouse performs during the 46664 concert in celebration of Nelson Mandela's life at Hyde Park on June 27, 2008 in London. Sadness takes on different forms, from regret to depression to loss; ...