As the title says, I'm looking for either something really deep and depressing or a tear jerking tragedy. I prefer that it's either shoujo or shounen but it's fine if it isn't. I'm not sure where this helps much but I'm also looking for series similar to Orange (TAKANO Ichigo). Sorry that this is quite vague and thanks in advance!

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Deep Love - Ayu no Monogatari & Deep Love - Reina no Unmei beware: mature topics
Hajimari no Niina

in need of romance?
uncommon, sad, sweet

Toki wo Kakeru Shoujo - Tokikake

If you want something really deep, you should go with seinen/ josei, you'll find more titles than in shounen/shoujo.

These mostly seinen:
Oyasumi Punpun and other works of Asano Inio, he tends to write melancholy, depressing stories.
Arigatou
Planetes: not depressing, but I found this has some deep thoughts
Real: again, not depressing, but definitely deep.
Watashitachi no Shiawase na Jikan: a bit tear-jerking
Death Sweeper: only 2 chapters scanlated, but I think it has potential to be a deep story.
Saikyou Densetsu Kurosawa

And seconded Deep Love series.

art thou open for animes?
if yes then I recommend Hotaru no Haka
for manga I have no clue, sad manga stories anger me instead of making me sad.

[img]http://oi44.tinypic.com/1z37xvk.jpg[/img]

Recently there have been a few topics quite similar to this one, so maybe those will be worth a look...

Dark Undertone/Unexpected
Tragic Shoujo/Josei and/or comedy shounen request (Weird, no?)
Desperate Main Characters
Good Tragedy (is there such a thing...)
Tragedies with a satisfying ending
Heart wrenching with excellent character development
... ^^"

"It's like love is a bonus in your life. Even without it, I'm just fine. I don't feel like pointlessly searching for it. You don't have to make yourself unhappy." (Ookami Shoujo to Kuro Ouji)

"Why does it rain?" - "To create drama." (Drops (Andou Yuki))

Um, assuming that you're fine with non-romance series...

Bokurano
Vampire Juujikai
Alive - The Final Evolution
Clover (Clamp)
Tokyo Babylon
Gunslinger Girl

Peach Girl (although you probably have read this already)
Confidential Confessions
Full Moon o Sagashite
Kimi no Sei
Terra E
Vampire Knight I guess it's thought provoking? It's not as good in my mind though... >.<

[img]http://i305.photobucket.com/albums/nn232/laurelkath/Random%20shit/loreal.jpg[/img]

Deep Love - Ayu no Monogatari comes to mind. If this manga had used puppies to club baby seals, it would have had a more cheerful ending.

The whole series is sad. I stop reading it after the first one.

You are now inside my Tsukuyomi. For the next 72 hours... I will slap you with this trout...

Resistance is amusing...

The best tearjerker is Twin Spica.

[img]http://oi50.tinypic.com/1p7xj6.jpg[/img]

Hardly anything makes me cry anymore, but some things do manage to evoke emotion.

Air Actually, I think the anime is more successful in making a person tear. After seeing this, I wanted to take on the world's pain.

Clannad I never watched or read this all the way. After seeing the sad scenes, I never had the desire. Anime is better in my opinion.

Fruits Basket The manga only.

WATASE Yuu This woman doesn't want anyone to be happy. I'd you specific titles, but I want to ruin your world. JK?

Chrono Crusade Terms of crying, the manga might be better.

Fullmetal alchemist can do this to some whatever the version. Though if you really want to stab someone in the heart, watch the first anime (which after a few episodes was nothing like the manga). It's a mixture of a mind screw and a tragedy.

I second Full Moon o Sagashite and Oyasumi Punpun.

I like my men androgynous.
I like my women androgynous.

Natsume's Book of Friends

totally second/third the Deep Love series.

[img]http://img267.imageshack.us/img267/4466/princesswallpaper2560x1.jpg[/img]

"In a world where most people would be crazy, then it would be normal to be crazy and crazy to be normal... but then again, if you were normal, then you would be crazy... isn't it crazy what a paradox a little craziness can create?"

Full Moon wo Sagashite -->First anime ever to make me cry! seriously total tear jearker!

Flower that blooms in you ( Third oneshot) --->http://www.mangaupdates.com/series.html?id=12093 --> Wow first manga to ever make me cry !! 😃 😃

Rec - Kimi ga Naita Hi