Lyric discussion by wonderousone 

Cover art for Grey Street lyrics by Dave Matthews Band

I saw an interview with dave and this song represents depression, thinking and listening wondering how did i get stuck here, and is it up to me to get myself out of this and everything being grey, and stuck on grey street, the other version of lyrics saying how she would use colors bold and bright, it a magnificent song, and from what he said if you ever been depressed you know exactly where grey street is, i believe it was on a an E entertainment show or VH1

That's the sense I get from it. When you are depressed, no matter where you go, no matter who you meet, no matter what you TRY, everything is effected by the same bleakness. Someone can give you the most beautiful advice on life, and they can seem crazy because it cannot apply to you because you are stuck "on a dead end street at the end of the world." Given humans' tendency to confabulate their own version of truths so there is no dissonance with what they are experiencing, I think that someone gave the character in this song good advice,...