were i still in high school, i would spend *a lot* of my free time crying 
to laura holloway from the 80s jem cartoon singing "alone again"[1]. i 
still do tear up a bit upon hearing it (high-pitched voices do that to me all 
the time), but i can safely say i relate to laura's problems of being alone 
and not liking herself a bit less nowadays.

"nightmare" sung by jem[2] in the same cartoon episode is also pretty sad, 
especially with the trippy visuals accompanying the lyrics about being 
lost and confused amidst the cruelties of the world. the whole episode 
(titled, unsurprisingly, "alone again") itself is quite upsetting 
with its theme of depression resulting in drug addiction, yet still an 
interesting watch, albeit somewhat creepy at times (because drugs, DUUH). 
(it's also definitely better than those many episodes with cultural 
appropriation moments and that one ep where jem sings about how she can 
enjoy freedom in america after the usa government stole/confiscated and 
almost destroyed her very important and top secret hologram-making machine aka 
synergy, that's for sure)

alas, i fail to acknowledge how "look inside yourself"[3], the song from 
the end of the very same episode, is supposed to help me with my 
self-esteem issues and social anxiety (this can be said about a lot of jem 
and the holograms' inspirational and motivational songs for me, actually). if 
anything, i feel better about myself when singing the misfits' "universal 
appeal" or "designing woman". meeehh, let's count this one sad as well. 

why am i writing about this, you may ask? i've recently found myself on a 
hunt for depressing songs, so if you'd like to listen to something sad, 
these are my recommendations for you. i could also recommend you the music 
of teen suicide the band, though it's a bit more mainstream sound of 
sadness, in my opinion.

...alone again, in gopherspace
   alone again, in this nice yet lonely place...

-----
[1] - https://youtu.be/-alJe-7Upcw
[2] - https://youtu.be/8QTM-ticThQ
[3] - https://youtu.be/lDxpHNdltS8