50 Songs That Are Guaranteed to Make You Cry

Strip away the creeping pumpkinspicization of fall, and there’s something somber and inherently melancholy about this time of the year. It’s when the days get shorter, the leaves fall off the trees, the skies are gray, and the air is cold enough to demand scarves and hats. And it’s also the time to huddle up by the open fire, drink tea, and listen to sad music! With that in mind, here’s a playlist inspired by our recent list of heart-wrenching movies — an epic selection of songs guaranteed to make you cry, from the tear-jerkingly forlorn to the moving and beautiful.

Big Star — “Holocaust”

We might as well start with what’s perhaps the bleakest song ever written, hey? This lyric is one of the saddest in rock’s canon, cataloging the slow disintegration of its subject and culminating in the lines, “You’re a wasted face/ You’re a sad-eyed lie/ You’re a holocaust.” The instrumentation — ghostly echoes of slide guitar and a distant piano — only make the whole thing even more distressing.