(2) Concrete Blonde, "Joey"
“Joey” remains my favorite song from my high school self’s favorite album, Concrete Blonde’s Bloodletting. Yes, it’s kinda about vampires, but it’s mostly about loving doomed people. And Joey is the most doomed, “somewhere drunk / and passed out on the floor.” Joey offers no endearments or excuses, he’s not even really present in the song, which, despite the video, feels like a song sung in lead singer’s Johnette Napolitano’s head to an absent lover (Napolitano later confirmed that the song is about Marc Moreland of Wall of Voodoo, who eventually died of liver failure). She offers him money, forgiveness, and love, but the song’s last lines “Oh / Joey, I’m not angry anymore” feel more like resignation than hope. The song was the last one recorded for Bloodletting, because Napolitano didn’t want to sing it.
(15) Psychedelic Furs, "Heartbreak Beat"
Not to get meta, but “Heartbreak Beat” is not a sad song so much as it is a song about sad songs. It’s about wishing you felt more, but knowing that the world’s endless soundtrack of love songs are not about you, that in your relationship “...the world don’t stop / Every time that you call.” So maybe you end that relationship and go looking for that “perfect kiss, somewhere out in the dark.” But then! “Heartbreak Beat” comes on the jukebox just when you catch a glimpse of your ex across the bar. For a second, it feels like love, but then you remember. You brace yourself for the sadness, but instead you feel nothing. Which is sad, no?