This is my favorite song off Elliott Smith's comeback album, which became his posthumous album, From a Basement On the Hill...
Smith had been stuck in a long period of drug abuse and depression leading up to this final creative effort. His last few albums had begun to suffer, as his negative tendencies appeared to send his life into malaise. With From a Basement On the Hill, I still don't think he fully emerged back to greatness, but the effort of the comeback was so beautiful and (in hindsight) so doomed that it's crushing.
While I don't think the entire album is as strong as his first few, I don't think there can be much argument that "Pretty (Ugly Before)" is great. It was actually a single released ahead of his final album, included posthumously in the album to enhance it, but it was clearly part of the entire new creative effort he mounted to right his life, and so it belongs.
Elliott Smith was a confessional writer who did not spare us from his struggles and insecure thoughts. The painful frailty in this song, describing his fears of "ugliness," is conveyed in a heart-breakingly direct way.
Beyond the lyrics and all those difficult ideas, there is a music of peak Elliott Smith delicacy and brilliance. The verses are really only two chords with a nice defending cadence between them, but the cadence is a great orchestration, and the two-chord sequence ends with a quintessential Elliott Smith chromatic guitar run. Creative use of chromatics were a natural part of all his melodic ideas.
The choruses begin with a short introduction allowing a cool little vocal run. The main chorus takes excellent steps downward until the key resolution of the whole song, this drop into the F chord, beginning a cadence into A minor. It's the song's actual heart breaking.
The piano and guitar instrumental at the midpoint is enthralling.
The power of the song almost escaped me at first. It kind of came off as just a song. Then it would come on in my rotation, and my brain would tell me that I was happy. The song became more and more welcome each time it appeared. I found myself waiting for that eventual, heavy drop to the F chord, all the lament thrown into that moment of musical expression. In that moment, my empathy and appreciation go out simultaneously to this lost musical soul.