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Windaria

Alt titles: Once Upon A Time

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In a land filled with magic and mystery, two rival kingdoms are readying for war: Isa, the beautiful water-laden city, and Paro, the industrialized wasteland. Windaria follows the tale of two sets of lovers: Marin and Izu, a young pair of farmers who are devoted to one another, and Ahanas and Jill, princess and prince of the rival kingdoms. With war approaching, these star-crossed lovers will experience the true depth of tragedy as they struggle to survive.

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Nausicaa Of The Valley Of The Wind

Alt titles: Kaze no Tani no Nausicaa

Nausicaa Of The Valley Of The Wind main image

One thousand years after the Giant Warriors caused an apocalyptic event known as the seven days of fire, humans are living in constant fear of the Toxic Jungle. This ever-spreading forest is filled with poisonous plants and gigantic monstrous insects; even the very air is deadly. Nausicaa is the kind and wise princess of a small, peaceful country known as the Valley of the Wind, which has so far avoided the spread of the forest. One night a large airship containing one of the Giant Warriors crashes into the valley. The following day soldiers from the powerful nation of Tolmekia invade the Valley of the Wind to reclaim and revive the warrior. As the only one who truly believes that there is a way for humans to live alongside the insects, Nausicaa must find a way to stop the war that now threatens her people and protect the Toxic Jungle before the Tolmekians burn it to the ground.

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sothis
Nausicaa and Windaria definitely have a different feel (Nausicaa being a tad bit more light hearted, Windaria being an extreme tragedy), but for some reason I got a similar feel from watching each of these. Nausicaa was the first thing that came to mind when watching Windaria, perhaps for its animation style, or fantasy themes.
Rar
Nausicaa seems to have been an important influence on Windaria, with similar themes and appearance, and the same techno-fantasy setting. Despite being an earlier film, if anything the animation is better, and takes a slightly more subtle approach to delivering its message of conservation and peace. Finally, Nausicaa is more light hearted and optimistic, so will cheer you up after the heavy tragedy of Windaria.
Dragonstar
WINDARIA, and the even poorer hatchet job ONCE UPON A TIME, are direct ripoffs of NAUSICAA. WINDARIA was, in fact, created solely to bring Miyazaki's story to America at a time when direct Japanese exports were harder to accomplish. The comparison between the two is so obvious that it barely needs support; this recommendation exists only to point you towards the superior NAUSICAA, on the off chance that you aren't familiar with it.

Now and Then, Here and There

Alt titles: Ima, Soko ni Iru Boku

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Amidst a beautiful sunset, Shu is violently whisked away to a grim future devoid of water, and empty of hope; a place where children are forced to become soldiers, and kill countless others in the name of King Hamdo. Shu's companion is a mysterious girl named La La Ru, who may hold the key to survival. Now, he must concentrate on the only things that matter: escaping Hellywood, and finding a way home.

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sothis
Not only do NTHT and Windaria both deal with the grim effects of war, but they both are extremely depressing and sobering because of it. I highly enjoyed both, and think you would too. (Though Windaria does have a lot more fantasy in it)

Battle Angel Alita

Battle Angel Alita main image

Among the garbage dumped down from the mysterious aerial city of Zalem, a new life is found. Restored by a brilliant cyberneticist, a young girl named Gally struggles to find her own place in the world, to learn the extent of her own deadly abilities and to discover that which makes her truly human: love.

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valondar

Both of these anime are ultimately about people who place hopeless ambition over remaining with one's loved ones. And though Battle Angel Alita is cyberpunk and Windaria is fantasy, something about their standard, old anime look is rather similar. Windaria is the more tragic of the two, and Alita has a greater reliance on action, but I think a fan of one will appreciate the other. 

Princess Tutu

Princess Tutu main image

Once there lived an eccentric author called Drosselmeyer who wrote grand tragedies - one of them was the tale of a prince who sealed away an evil raven by breaking his own heart into tiny pieces. However, before the story could be completed, the author died and the tale took on a life of its own. Now, in a town where fiction and reality meet, the story continues on its tragic course with Ahiru, a duck who transforms into the beautiful Princess Tutu in order to restore the prince's heart. But will Ahiru's act of love be enough to defy the story's terrible destiny and lead to a happy ending?

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NoSanninWa
Windaria and Princess Tutu are both fairy tale tragedies full of darkness which explore the true nature of the human soul.

Saikano

Saikano main image

In the not-so-distant future, mankind is at war with itself. The lives of Chise and Shuu are torn apart when Chise is chosen to become the ultimate weapon to fight for Japan against their enemies. Death, sadness, and the hardships of love accompany Sai Kano in its grim look at war and its consequences.

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Bateau
If you love films about tragedy and sorrow, then these two are a must see!!!!!!. Both are simply spectacular!!!