Kanon 2006, << Too forced.
Shigurui, << Nope
Saikano, << Sad, but not saddest.
Here and There, Now and Then, << Close contender for #1
The Girl Who Leapt Through Time, << Quite sad, but not saddest.
bokurano, << Depressing, but not sad.
Clannad, << Forced sadness is forced.
Air(The movie), << A little bit.
Grave of the fireflies. << More depressing than sad.