All of the songs Lou Barlow wrote on Sebadoh's "Bubble & Scrape" LP are immensely sad.
He had just broken up with (what I think might have been his first ever serious) girlfriend (and he's got a reputation as emotionally unstable in the first place), so he's whining and ranting and tearfully wanking himself to sleep all alone, no holds barred going through all the stages of pain & grief & separation. Remarkable spleen-venting songwriting.
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