The entire "Pretty Hate Machine" album from Nine Inch Nails is associated with my last year of high school, and attached to a hot but abusive relationship I was in.
The Eagle's "Hotel California" is associated with me being stuck in the psych ward for a bit, it constantly played on the radio (one of the very few sources of entertainment) and it felt like the universe giving me a fuck you.
Somehow I do not hate any of these songs or feel too bad about anything while listening to them, thankfully, because it's good music.
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