I'm in the mood for some Say Anything.
I actually don't normally listen to this band much, but Is A Real Boy is the exception (specifically the original, most of the songs on the extended edition don't fit the original album concept and flow). Somehow this album only had 20k sales, but it perfectly captures the mental struggles Max Bemis was going through at the time(undiagnosed bipolar disorder, literally had a mental breakdown and got institutionalized writing it). Unlike 99% of the mid-2000s "emo" trend, this album is genuinely introspective and not just sad or rebellious for the sake of selling to teenagers.