Season three (Tamers) was made by the same person who did Serial Experiments Lain, which might explain the fucked-up-ed-ness.

And also why it's the best season of Digimon.

Tamers was fun in the beginning, surprisingly bold in the middle, and Dark as hell in the end. It's no wonder i loved it so much as a kid. I really wish it was followed up instead of being a one-off season like most every other Digimon series because the characters in it were actually interesting and worth a damn.