Secret Base ~Kimi ga Kureta Mono~, from AnoHana. I can't bear to listen to this damn song without wanting to cry.
Sis Puella Magi, from Mahou Shoujo Madoka Magica. When I listen to it, all I can think about are the sad moments from the anime.
All of the Higurashi openings are really emotional, too...
And,of course, Elfen Lied's Lilium.
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The opening from Kanon 2006, it gives me chills everytime I hear it, because everytime I hear it my brain just connects it to all the sadness and crying I had/did during the series. I almost cry just from hearing the song, makes me think of Makoto etc. :'( So sad...
Elfen lord's Lilium (especially the musicbox version)
Higurashi's You (visual novel)
Most of clannad's songs, the one that played during the tomoyo-ushio scene ;-;
Ending of toradora (orange?)
Beck's moon on the water
AnoHana's ending, secret base.
nana's ending, a little pain
Dango Daikazoku from Clannad is one of my tear-trigger songs so I would vote it as the most emotional anime song I have heard yet. Kanon opening is also a pretty emotional song too, heard it way before I watched the series but since I finished watching it has taken on a new level for me.
I posted my songs here, but then I heard new songs. They were sadder, more emotional, yet they didn't break me down like ones I posted.
Well it also depends on the anime. They can make saddest song ever and play it with some stupid scene so it will not make you cry or feel sad at all. Or sometimes they can give you very,very sad scene and a song which is not that sad, but to you it will be most emotional song ever.
For me that's the case with Angel Beats OP My Soul, Your Beats... Just because anime is able to make you sad song sounds even sadder.
Also Continued Song, which is undoubtedly sad, is not that sad, but with that final scene (death and last scene with cart driver) it is amazing and you wanna cry your eyes out. On the other hand we have Innocent Days which is sadder, and music is more depressing, yet I never cried like I cried on Continued Story.