Off the top of my head I have a few random references for a variety of sad listeners. Whether you're dumped, cheated on, lost, doing hard drugs, isolated, or just seasonally moody I believe I have you covered. I'll come back if I think of anything else.
(Radiohead) Radiohead - There, There (The Boney King of Nothing)
(Early 00s Mildly Poppy Indie) Hot Rod Circuit - At Nature's Mercy
(Late 90s Sad Math Rock) Braid - Forever Got Shorter
(Folk Emo) Owen - A Bird In Hand (OR American Football - The Summer Ends)
(Relevant Shoegaze) Whirr - Formulas and Frequencies
(Surprisingly Miserable Melodic Club Music) RAC - If You Forget Me
(70s Sad Holiday) Joni Mitchell - River
(00s Mainstream Punk) Sum 41 Pieces
(Contemporary Lo-Fi Dream Pop/16 Candles on Prozac) Procession - Spring Thaw
(Late 90s drop-tuned misery) Deftones - Digital Bath
(00s indie/emo boiz) The Early November - Everything's too cold, but you're so hot
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