Inspired (probably obviously) by the “movies that make you cry” thread.
For me it’s A Christmas Story by Truman Capote:
Makes me cry every time I read it. And I don’t mean just tear up, I mean bawl.
Your picks?
Edith Wharton’s False Dawn every time I read it, and The Old Maid sometimes, if I’m in the right mood for it.
The Little Match Girl, Hans Christian Anderson. 
Every year I read the book “Walk Two Moons” to my fifth graders and every time I read the part about Sal’s stillborn baby sister, I can barely get through it. Last year, one of my students asked if I wanted him to that part to the class for me.
I bought “The Yearling” last week thinking my sister could read it to my nephew. However he’s only 5 and this book is a tearjerker of such magnitude it makes “Old Yeller” look like a laugh riot, so I guess he won’t be getting a copy for a few more years.
“Charlotte’s Web” was the first fictional work of any kind that ever made me cry. Obviously as a child, I cried for just about any reason.
But when Charlotte said goodbye to Wilber, this 6-year old had to run for Mommy and cry for a good 20 minutes.
In contemporary times, there are two films which always make me cry: “The Joy Luck Club” and “A League of Their Own”. Mainly because both involve the death of a woman who was about the same age as my mother.
And the all time weeper in any situation, and it’s come up on threads like this before, is the Japanese anime “Grave of the Fireflies.” If you can watch that without crying, you need to see a psychiatrist for treatment.
~ Philip Pullman (as if you didn’t know).
I bawled like a little child. There is also The Fionavar Tapestry, which turns me into a soggy rag.
Most embarassingly, [spoiler] there are a few of the Buffy franchise books that have made me cry, especially Child Of The Hunt and the story Again from Tales Of The Slayers, Vol. II.
The worst offender was Blood and Fog though, which made a fool out of me because I was reading it in public. I’m putting this in a spoiler box because it’s embarassing.
[/spoiler]
I haven’t cried at a book or story in years. But I remember whenever I read Where the Red Fern Grows, I just lost it.
Bridge To Terabithia and Where the Red Fern Grows.
Thirding Where the Red Fern Grows, and adding A Time for Dancing.
The Last Unicorn and Black Beauty. sniffle
The Martian Chronicles, by Rad Bradbury.
A Wind in the Door, by Madeleine L’Engle.
Wow is it only children’s stories that make us cry? 
The first time I ever cried from reading was Gary Paulsen’s “Winterkill”…I don’t even remember what it was about anymore, really. I just remember feeling really weird that a book made me cry. And I CRIED HARD.
Now I have to go find it and read it again
Gardens of Stone.
The movie sucked big donkey cock. The book, though. . . the bit where the girl knew that letting him go was likely to mean his death? Yeah. Cry like a baby every time I get to that.
The Abandoned (aka* Jenny*), by Paul Gallico
I cried at the end of Watership Down. Stupid rabbits.
I also got a bit weepy at the end of Stephen King’s Bag of Bones. The little girl in the story reminded me of my niece for some reason, so the ending hit me pretty hard.
Where Late the Sweet Birds Sang by Kate Wilhelm. It’s a Hugo Award-winning (1977) post-apocalyptic SF novel that left me in a funk for days afterwards. Which is probably why it isn’t more widely read. It’s very well written, incredibly poignant, and has been a major influence on my views about humanity and our role in the Earth’s ecology. I have yet to be convinced that Wilhelm’s scenario isn’t going to happen.
“The Swan” by Roald Dahl.
I cry every time I read it.
"Stones for Ibarra" by Harriet Doerr.
This short novel is a series of interconnected stories about the experiences of a married couple from San Francisco who go to Mexico to manage a silver mine that the husband has inherited. After settling there, the husband discovers he is dying of cancer, and the wife learns to cope from what she has learned from the people of the village.
There was a TV movie made with Glenn Close and Keith Carradine, but none of the poignancy of the novel made it to screen.
"JT" by Jane Wagner
I posted this on another thread. This is a children’s story about a troubled young African-American boy who starts caring for an injured cat. His mother has almost given up on him because he’s started stealing, and he’s harassed at school, but he starts to lavish the love missing from his life onto this cat, making a nest for it in an abandoned oven, and stealing cans of tuna fish to feed it.
One day, when he is visiting his cat, the two boys find him, and scare the cat into the street, where it is run over and killed. Instead of making him bitter and angry, he starts to take control of his life, and those around him begin to pay attention and care for him more. The grocer who he stole from gives him a kitten for Christmas
Just remembering the part where his grandmother asks “What you want for Christmas, boy?” “A cat. I want me this cat I found,” has made me well up.