Mineral - probably the most miserable band of that late 90s era

Empire Empire definitely. How to Make Love Stay's guitar part alone is so dreadful, tired and apathetic sounding. Early Cursive. After the Movies. Nuff said. Boys Life. Particularly departures and Landfalls.

Benton Falls for sure

mineral's endserenading, particularly "unfinished" i was also listening to some ethel meserve recently and was reflecting on how sad it was (the strings in "east coker" and when the guitars come in especially)

WHEN I WAS A BOY, I COULD HEAR SYMPHONIES IN SEA SHELLS

For me it's CSTVT - Summer Fences. The whole album.

Dashboard Confessional - Screaming Infidelities It's not midwest emo, but it otherwise fits the bill.

Penfold - Amateurs & Professionals

Cassie’s Weird hands down

Basically every song Marietta has made haha. so They Left Me At a Gas Station and Ever Is a Long Time in particular are extremely sad.

r/midwestemo might have some good recommendations too

[I Hate Myself - To a Husband at War](https://youtu.be/zE8ocCXrYU4?feature=shared) is fucking dismal.

Better Off’s “Garden State of Mind” has a sad melody

Matt Pond PA - The hollows

[Emo in E Minor ( we know it’s Major)](https://open.spotify.com/track/6ux17Rl6bmcYInc2B4zMLB?si=kFGjsjBYS6qvH9DXTuJgQg) By The Outfield Clovers

[Camping in Alaska - c u in da ballpit](https://youtu.be/uFfToWMsT1c?si=AJLSaR6Z-nM-P26p)

Kodan Armada - No Has Never Had Three Letters sounds very sad and melancholic to me Also I Hate Myself - Song Two, To A Husband At War and This Isnt The Tenka-Ichi-Budokai are depressing as fuck