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(the playlists do just consist of one specific song exactly 100 times btw)

I feel like those song titles / pictures are weirder than listening to songs on loop

Try getting obsessed with long songs so you don't need to replay them constantly, once at it choose better your music. Try Wagner.

@Manko-sensei - I have two copies of the entire Ring on LP, including Solti's version, but I'd be inclined to suggest something along the lines of German symphony cycles (Brahms [4], Mendelssohn [5], Beethoven [9], Schubert [10, depending how you count], Mahler [10], Mozart [41-ish], or Haydn [104]).

@Angry_Panda of course, one of the reasons I suggested that is because it's one of those works that people only know partially (The Valkyries in this case, I use that as an alarm). You can't go wrong with those!