The Nashville Ramblers - "The Trains" (1983)

To be perfectly honest, I know almost nothing about this band. A quick google search could probably change that, but I don't want to ruin the mystique of this song by knowing too much about it. What I do know is that this is quite possibly the best song ever written.
From what I understand, the Nashville Ramblers were both a San Francisco and San Diego band. It's likely that they have recorded more songs, although long standing legend has it that this is the only one. The title of the song is apparently a reference to San Francisco's muni cars, which adds an amazing amount of romance to what is other wise a standard power-pop broken heart story. There is more amazing emotion and palpable heartbreak in the vocals of this song than nearly any other I can think of. I really, really hope you enjoy this. It is very truly one of my favorite songs of all time.

The Smiths - "Still Ill" (1984)

"Still Ill" is a song I simultaneously wish I could relate to, but am glad that I don't. Over the the course of about three and a half minutes it almost perfectly sums up what Morrissey is about. A mission statement in a way. This is a song about self loathing, inexplicable narcissism, inappropriate condescension, the hatred of work, bizarre references to violence, tongue in cheek jokes and beautiful romantic moments with people who disgust you. The one major Morrisseyism that it's lacking is the glorification of criminals.