This is a way I gauge if I can get along with a person or not. They MUST have this in their collection or I get a strong feeling that I'm not going to end up liking this so-called music fan. Without further ado...Neutral Milk Hotel-In The Aeroplane Over The Sea.
I know where you can get a nice pair of blinders custom made to your size so you don't even have to be distracted by the site of those people ;-)
That particular CD has been recommended to me so many times that now I'm gonna' have to get a copy just to see if I can be your pal.
Another one that comes to mind, given that recommendation, is Bright Eyes (Conner Oberst). I suspect, like Neutral Milk Hotel, this may be an acquired taste, and is certainly not for everyone. I'd suggest checking out the album, "Lifted or The Story Is in the Soil, Keep Your Ear to the Ground", to see if you might be a fan. There is one tune of his that you can download for free on iTunes - "When the President Talks to God". It's not particularly typical of Oberst, but might give you taste of what he's about in one sense. This is a pretty conventional composition, whereas his albums tend to be more layered, complex and musically creative.
Marco