The Best, Most Depressing Songs

There is no shortage of sad music in the world. Just reference most love songs, a substantial chunk of country music, and the entire genre known as “the blues”. But there’s sad and then there’s DEPRESSING and that’s the bit we seek to dive into with this episode. We talked to three top music critics: Steven Hyden of Uproxx, Craig Jenkins of Vulture, and Ann Powers of NPR and asked them to provide their picks for those songs that are relentlessly depressing but yet have the surprising power to make the listener feel better or at least more understood. Our playlist of dark hits features many feel-terrible classic, a depression-makes-me-feel-nothing jam, and one song so relentlessly happy that it might make you feel genuinely upset. Join us on this emotional and musical rollercoaster.

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