Well the first album I ever got new was Scarlet's Walk, so I'm ranking on connection from when I first heard them:
1. Under The Pink (PGY was the first song I ever heard and the song that made me a fan)
2. Choirgirl
3. Scarlet's Walk
4. Venus
5. Little Earthquakes
6. Native Invader (Reindeer King on it's own ranks higher)
7. ADP (loved it when it came out and played it to death - it hasn't aged well)
8. Unrepentant Geraldines
9. Pele (took me the longest time to get into this one, hence the lower ranking)
10. The Beekeeper (I adore it now, hated it at the time)
11. AATS (still hit and miss with this one. I'm a lyrics boy and whilst the music is good on this one, the lyrics still don't grab me)
12. SLG (me on first listening: THESE ARE NOT TORI AMOS SONGS)
13. Midwinter Graces (I fucking hate Christmas)