The two I can think of are:

  • It’s Not Unusual
  • Escape (The Piña Colada Song)
  • zlatiah@lemmy.world
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    15 days ago

    Someone else mentioned this too, but if anyone is into Japanese songs: I think there are probably more songs (especially Vocaloid ones) with extremely messed-up (and convoluted) lyrics than those that do not… I don’t think most of them are well-known outside anime/vocaloid circles though. Trying to think about the more “cute and depressing” ones I could find:

    NSFL

    These are just what I could think of for now… A lot of songs with mentions of depression, suicide, etc… Other forms of messup, Telecaster B Boy is about being trans & not fitting in society I believe (song is a banger)

    And this one is not “depressing” as-is, but Senbonzakura (that super famous Japan-esque song sung by Hatsune Miku that everyone has heard of) is about Imperial/WWII Japan sooo… take that as you will