Baltimore is definately one of the goofiest, most terriblist songs ever. But it was the 80s hair phase, before her rebirth, so I’ll forgive her.
Little Earthquakes actually has he most accesible lyrics. They may not seem that way at first, but most of the songs have a very discernible idea/story to them. Even the really out there stuff refers to intelligible things. If you don’t know what “Neil and the Dream King” refers to, that’s your loss. 
Under the Pink is a fabulous album, but it’s lyrics are a little more obscure and very surreal. I really, really like the music on this one.
Boys for Pele is also fantastic, but even more hard to discern. At this stage, she’s gotten into really almost nonsense lyrics, but the thing is, if you’ve listened to the first two, you can sort of make sense out of the sort of emotions each line is trying to convey, even if they don’t seem to make sense individually.
Choirgirl is where, for me, she lost something. Still some great stuff, but the lyrics just don’t work as well for me, and some are rather grating. I think Scarlett’s walk is much better than the three albums before it, though I wish she’d rock a little more: it’s hard to get people into it when it feels so easy listening.
The thing about Tori’s best lyrics is that they jumble all sorts of images and ideas and stream of consciousness stuff together: but then one really killer line suddenly pulls it all together. Tear in My Hand is a good example: seems aimless enough at first, but that “maybe she’s just pieces of me you’ve never seen” line really drives it home. A great great lyric, and the kind she doesn’t pull off enough in her middle years.
I think the most fun thing about her, though is the… what do you call it? its a p word having to do with mishearing a lyric. There are tons of lyrics I thought were totally different before reading the liner notes. For instance:
Honey
I heard “you’re just to used to mourning” and “you always let your babies die” (an eerie and sad mishear in retrospect)
the real lyric “you’re just to used to my honey now” and “you always like your babies tight”
Taxicab song
I heard: “I bring you a message”
the real lyric: “I’m glad I’m on your side”
I always loved Take to the Sky. It was one of the first songs she wrote when starting over, and it’s a great rocking introduction. Too bad it’s a B side.
