6. Tepid Peppermint Wonderland by The Brian Jonestown Massacre
I sort of love The Brian Jonestown Massacre. Their blend of psychedelia is particularly witchy. They sound like The Velvet Underground and The Seeds but also totally original. Admittedly, this isn’t the most depressing record on the list—some songs will even make you dance/sway—but it’s dark in the sense that you know the band is on A LOT of drugs. The lead singer sounds tortured and sad even if the music itself sounds uplifting. This album was sort of my go-to whenever I would take drugs. Listening to it high made you really “get” the music. Now that I’ve listened to it sober, I realize that kind of thinking is, well, stupid.
7. Suburban Light by The Clientele
The Clientele made some really stellar dreamy records in the early ’00s. Now, they’ve gone in a more polished pop direction and aren’t as good, in my opinion. But Suburban Light was a perfect nighttime record soaked in reverb. The jangly guitars, lazy and distant vocals, and delicate drumming made their sound positively precious. Songs like “If We Could Walk Together” and “Five Day Morning” make me tear up every time and I’m not even sure why. This is purely a nocturnal record though. Play it on a rainy night in your bedroom and get blissed out.
8. Pink Moon by Nick Drake
I know you’re probably like “WTF” about me posting the VW commercial featuring “Pink Moon”, but it actually accurately sums up my feelings about the record. It’s late at night and you’re feeling something with your friends, you’re having a moment. The music has put you in a cocoon and you don’t want it to burst so you just keep driving in silence and feeling thoughtful. I don’t know. That’s what this record feels like to me. It’s also a nocturnal record, it’s sad, it’s pensive. Bummer Nick Drake killed himself but also not surprising.
9. The Greatest Hits by Simon & Garfunkel
I included their greatest hits because I didn’t want to limit myself to just one record. Simon & Garfunkel makes me feel SO emotional. Songs like “Bookends” and “Kathy’s Song” always cause me to tear up. They were the musicians who wore their hearts on their sleeves and weren’t afraid to look uncool. They weren’t interested in making sexy rock and roll songs like Led Zeppelin or The Doors. They just wanted to make something pure and honest, and they succeeded.
10. Singles by The Smiths
I couldn’t ignore Morrissey especially since his music sort of changed my life in high school. I remember the first song I heard from them was “That Joke Isn’t Funny Anymore” and having my mind just flood with emotion. Singles is a great introduction to the mopefest that is The Smiths. You get all of their poppy radio stuff as well as their more melancholy tracks. Being sad felt so good when you were listening to them. Their willingness to go there and be depressed in the eighties was admirable, considering that everyone else was doing coke and dancing to The Go-Gos.