The 50 best sad songs ever written

Sometimes, a bad day calls for a shoulder to cry on. Others call for a stiff drink. And some days, you just need to throw on your headphones, crank up the volume and wallow in your own sorrow to the soundtrack of an emotionally devastating song that seems written exclusively for you. 

Sad songs come in all flavors, from breakup anthems to 12-bar blues. But if you’re just looking for a soundtrack calibrated to general malaise, this list is for you. And don’t worry… once you’re done (or just out of ice cream), we’ve got a stack of extremely happy songs to get you back on your feet. 

Best sad songs

Image: Ensign

1. “Nothing Compares 2 U” by Sinéad O’Connor

The original version of “Nothing Compares 2 U,” tossed off by Prince in the mid-’80s and released by the purple one’s protégés The Family, is a straight-up (and pretty forgettable) break-up song. But O’Connor’s version dialled the sad factor to 11, channeling the singer’s very real grief from the death of her mother five years previously. A superb vocal performance – the sound of naked sorrow – plus layers of weeping synth strings and an iconic, tear-streaked music video added up to one of the most successful sad songs in musical history. Pop music doesn’t get much closer to the bone.

"Hurt" by Johnny Cash

Image: Universal