Ano Hana sadest anime i've ever seen cried like a bitc.h
Tengen Toppa Gurren Lagann
Gosick and Toradora at parts
That's all that comes to mind.
Ergo Proxy, a personal favorite, is just a real downer show. 80% of the show is the main characters riding around in this post-apocalyptic, barren landscape that's simply depressing. 1 of them is always moody and kind of schizophrenic, the other is bossy, arrogant, and aloof, and the third is unsettlingly cheerful.
It creates a great atmosphere in this way and really take advantage of it.
The ending's pretty darn sad (man tears). I dunno...it got me kind of in a bad mood for a few weeks, but I absolutely loved it...the show, that is. I'd say check it out.
Link to the synopsis/reviews: http://www.anime-planet.com/anime/ergo-proxy
You should check out Clannad: Another World, Tomoyo Chapter and Clannad: Another World, Kyou Chapter.
They're one episode alternative time-lines, one where he's with Tomoyo and one where he's with Kyou rather than Nagisa.
Other than Clannad, 5 centimetres per second is my second favourite anime and is emotional.
Another emotional one I would recommendfor your tastes is Ano Hi Mita Hana no Namae o Bokutachi wa Mada Shiranai,Also known as anohana: The Flower We Saw That Day
Gosick doesn't have drama as it's main theme but towards the end and during certain scenes it can be sad.
Welcome to the NHK is also a sad anime but not in the same way Clannad is, it's more depressing rather than sad.
I feel like I'm repeating things people say, but Air, Kanon and Clannad are all really sad. Spice and Wolf have it's moments, too, along with Angel Beats! and Elfen Lied (Elfen Lied is more depressing then sad). Out of all of those, definitely go with Kanon. Saddest anime I've ever seen, but it's so good!
5 Centimeters Per Second will bring tears to anyone's eyes, not only that, the animation is absolutely stunning.. It's real life anime, drama/romance..
kanon in 06 trust me its super sad
I think it really depends on what makes you sad/cry.
Personally, I loved Clannad and Clannad After Story, but it didn't make me cry at any point.
I cried at Naruto Shippuuden, but I think that is because I have been following it for so long that I feel emotionally attached to the characters.
I cried when Ouran ended too, but they were happy tears! :)
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Also, Death Note made me cry for obvious reasons that I will not state in case anyone is planning on watching it xD
definately grave of fireflies and fruit basket
Angel beats is pretty sad it made me tear up but it's pretty sad itself
I'm not one of those people who cries a lot, but Elfin Lied sure did it
Only things not listed that I can think of are Saikano and My self Your self.
Clannad!!!! It's a beautiful Anime =)
Fantastic Children is a sad anime (Sci Fi, Mystery, Melancholy, Suspense)
try it for a change..
Mononoke-hime makes me sad ;_; cant think of anything else that others havent mentioned.