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Nice - I wish our archives were better, I know I've written volume in years past on Tori. My crash course:
Her first three albums - Little Earthquakes, Under the Pink, and Boys for Pele - were what made Tori into Tori. They're still remarkable and I would start there. Little Earthquakes is more direct and is just a powerhouse of songwriting and performance, voice and piano and lyrics all in full force. Under the Pink finds her expanding her palette a lot in terms of both songwriting and sound/instrumentation - it's a pretty sprawling record (though it's only about an hour long) and is probably my favorite from the period. Boys for Pele is when she really begins to stretch, bringing in the harpsichord and just an all around fuller and heavier sound. It's too long and a bit bloated in one or two points but still great. It's really hard for me to pick a favorite though there's admittedly some nostalgia going on - they're formative records for me both personally and musically. They released a live @ Montreaux show from the Little Earthquakes period that helps capture her live sound from that period, too - definitely worth a listen.
Her b-sides from this period were a big part of her career, too. They're more scattered across compilations at this point but it's worth checking out the last disc of compilation "A Piano: The Collection" -- there are some other bsides, I think, on the earlier discs on that set but most of them are on the last one. (I think that's on Spotify/Apple Music but could be wrong.) There were a *lot* of tracks from that period that could easily have been on an album and were cult faves among fans.
So I'd start with all of that. From the Choirgirl Hotel is excellent and should definitely be heard, imo, but it is often marked as the big shift in her career for sonic reasons. Less piano, more guitars, synths, etc., so I'd save that for after the early trilogy of records. Those four, I think, are the mandatory part of her catalog, along with the bsides.
Personally, several of the records following Choirgirl are still top-notch (especially the studio side of To Venus and Back and substantial portions of Beekeeper). But somewhere around then she lost the ability to edit: her records are just too big, too many songs, and they grow unwieldy. And by American Doll Posse (2007?), her songwriting is getting stale. She still shows glimmers of greatness in stuff from the last decade or so but a lot of it is tough listening (although I admittedly haven't paid them the attention they're probably due).
Would love to hear what you think of those early records especially - Apple and AMos share a common musical ancestor in Laura Nyro (among others) and I think those records are where it's most apparent.
-thebigfunk
~ i could still snort you under the table ~
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