The thing that has always struck me about In The Aeroplane Over The Sea is that it takes something familiar looking and retro (it looks kind of late 19th century/early 20th century to me) and gives it a bizarre twist. Like, what's the fucking deal with that chick?? Why is her face some kind of tambourine/coconut cut in half/whatever??
In the same way, the music takes something familiar sounding and gives it a bizarre twist. Whenever I try to explain the album to people, I always grasp for straws like "it's singer/songwritery, but weird" or "it's sorta like the Microphones if what's his face only released only one brilliant album instead of a bunch of pretty good ones and his voice was irritating at first but slowly you love it."