“Charlotte’s Web” and “Where the Red Fern Grows” (I’m an adult, I still can’t re-read that book…I’m such a wimp) obviously.
Guy Gavriel Kay (I didn’t know he was writing something new) tears me up.
But, and I’m ashamed to admit it, the last book that had me crying was “The Lion, The Witch, and The Wardrobe.” I broke up completely at the stone table.
I’m sure there are more, they’re just not coming to mind right now.
The Diary of Anne Frank. Read it when I was about 12. It left a very powerful impression on me.
Flowers for Algernon. Read this one maybe at age 16. Another one that has left a very strong impression. The question of what just makes you you still gets me thinking at night.
Any number of books I’ve read in the intervening years have made me think, but only those two have ever made me cry.
Now, if you want to talk movies, that’s a whole other subject! 
I think the only book that’s actually produced water from my eyes, ever, is Watership Downs, largely because I read it in two sittings because it was assigned for a class and I thought it was going to be as silly as the premise until I actually got around to reading it. I was vaguely attached to the characters after I took a nap after the first 300 or so pages and thought on it for a while, and then I almost felt as though I’d known them for years, being literally incapable of putting it down for up until the last three pages, where my eyes watered hard enough that I couldn’t make out the words. I knew it was exactly the perfect ending for the book and it’s what the main character would be happoest with, but I felt a part of me trying to kill itself as I read that.
On the list of “I just thought like I should feel something” afterwards, there’s…
The Remains of the Day by K. Ishiguro
The adopted daughter chapter from RAH’s Time Enough for Love and (to a lesser extent) his The Moon is a Harsh Mistress. Dementia, vegetative states, and otherwise being crippled have always made more of an effect on me than death, oddly enough.
Ursula K. LeGuin’s The Left Hand of Darkness had one of those few characters I actually related to (it’s impossible not to after all those ice chapters). The Suicide struck right to my heart.
The transition between the second and third books in Walter M. Miller’s A Canticle for Leibowitz made me feel pride in humanity, but the third book’s later reference to The Poet made me go through the anger stage of coping with sadness (which feels distinctly different from any other type of anger).
Mysteriously, my sixth-grade US history book killed me at what they presented as positive in their modern section. This was a rather poor district with books from the 50’s, you see…
Of course, anyone who’s not affected by reading the short Flowers for Algernon shouldn’t bother to pretend that they’re a human being.
I cried at the end of I Know This Much Is True by Wally Lamb. I didn’t have tears in my eyes; I was bawling. The twinship stuff and the schizo brother hit close to home.
I know this doesn’t count, but in my ninth grade English class we watched A Raisin in the Sun, the one with Ruby Dee and Sidney Poitier. I started howling when Willy ripped off Walter Lee. The teacher actually yelled at me to shut up. That scene–the one where he falls to his knees and yells “WILLY!”–still gets to me.
I can’t believe I’d blocked out my reaction to Harry Potters 3 and 5. OotP for the reasons spoiler boxed by Draelin and the third one (title of which I am too lazy to look up) when Harry is so close to getting to live in a happy home with Sirius, but it’s snatched away when Sirius has to go into hiding. Of course, the reasons for Harry having to live with the wretched Dursleys are made clear in book 5, but it was just too horrible in book 3. I’m convinced, however, that Sirius will be making a return somehow. Remember, he only fell through the curtain; he wasn’t beheaded or anything. His character was just too jaggedy – it felt incomplete. He has to come back. Or JKR is a worse author than that guy who wrote The Eye of Argon.
I think I just hijacked my own thread.
The end of Douglas Coupland’s Life After God hit me pretty hard.
Heinlein’s Podkayne of Mars. I have no idea why, but something about the ending just got to me the first time I read it, and every time since. It’s been years since I’ve read it; I’ll have to dig out my copy and see if it still affects me the same way.
I also remember once getting misty-eyed after reading his short story The Menace from Earth.
Those are two that come to mind. I’m sure there are more.
Oh WHY did you have to remind me about that one. The dog’s name was Amber, and he raves about what a beautiful dog she had been, and Herriot goes on and on about the poor nun who had been treating her all that time … <wanders off to have a good cry>
I never could finish The Plague Dogs.
Another weepy for me (at least when I was a kid, and I refuse to re-read it as an adult lest it provoke the same reaction): Tuck Everlasting
I forgot… there was this incredibly powerful short story I read when I was probably 13 that made me cry. I can’t remember where I read it or what it is called… it might have been called simply “Rose”.
It was about this girl that woke up with no memory and nothing but a rose tattoo on her behind and the nurses called her Rose. So she went to a tattoo parlor to see if they could tell her about herself. The man working there ends up tattooing her entire body, and everything he draws makes her remember something about her incredibly sad life.
In the end she pulls off her skin of all the tattoos she had done and leaves them behind as if leaving her old life there, and walks out with just her rose tattoo. This was such a moving story I cried terribly hard, even though I usually didn’t at 13.
Does anyone know this story?
Merla
I’ll second Night. It’s very powerfully written, but it’s the unflinching nature of the story that left me in ashes.
This didn’t make me cry, but I do think it’s sad: a Bradbury story, I think it’s called And there will come silent rains. Or maybe that line is just mentioned in the story somewhere.
The one about the automated house diligently caring for a family that was vaporized by a nuclear weapon years ago.
The Sound and the Fury by Faulkner
I don’t tend to cry much, but of those I can think of right now, I was choked up by Garp, the ending of *The Sirens of Titan * and some parts of Timequake.
The title is There Will Come Soft Rains. The story can be read here. The title comes from this poem.
Oh, gosh, I’m a terrible sap when it comes to books. LotR, definitely – it hasn’t gotten mentioned much in this thread. The ending of The Once and Future King really gets to me, as does Les Miserables. I’ve been known to get teary at Watership Down, and as I recall parts of A Canticle for Leibowitz, and I actually cried through the last few chapters of The Man in the Iron Mask.
If we can include poetry, then Robinson’s “Ben Jonson Entertains a Man From Stratford” always reduces me to tears – though this is a very personal reaction; it’s not exactly a sad poem per se. Wilfred Owen’s poetry induces the same reaction for a very different reason. And I once got weepy in class, rather embarrassingly, when the prof read Milton’s Lycidas to us…
And I know there’s plenty more. As I said, I’m a sap. 
Just remembered another one: The night I had my dog Axel put to sleep, I got drunk and re-read Harlan Ellisons’ “The Deathbird,” and cried harder than I ever had before in my adult life. But there were some special circumstances going on there. Didn’t make me cry the first time I read it, when my dog was still alive.
Just to let you know, there is an alternate ending to Podkayne. I won’t give it away (not even in a spoiler box), but you can find it in the book Requiem, along with some previously unreprinted material.
Glad to see there are others out there that feel as I do about Heinlein. Someone else seconded my vote for The Tale of the Adopted Daughter section from Time Enough For Love. One more story would be The Long Watch. Tears of pride on that one.
Huh? More than fifty replies without anybody mentioning Love Story by Erich Segal?
Me, the big sissy or what?
Amen.
This is the most incredibly visual, fast paced, bleak, desolate, grim book I’ve ever encountered. When they leave their concentration camp to march day and night in freezing weather with bare feet and the ragged clothes on their back and endure Jehovah Knows What during this forced march, and when they at last arrive at their new concentration camp, * and were happy to at last arrive there* I threw down the book and sobbed my eyes out for a good ten minutes.
Another book at the polar opposite is Harry Potter and the Goblet of Fire. The scene of holding off Voldemort with his wand and out of the want comes all the dead people he knows…and when his parents emerge I just lose it.
Some scenes in ** Donbas** leave me sniffling like crazy. Not as dark, but totally mesmerizing. If you like Night for all the grimness and startling power of the human spirit, I highly recommend Donbas. by Jacque Sandelescu. (sp?)
I had forgotten about that. I have a copy of Requiem somewhere, and now I remember reading the alternate ending, but I can’t remember it. (They say the first sign of old age is losing your memory; I can’t remember the second. )
The Brothers K by David James Duncan - bawled like a baby, then laughed out loud within several pages. INCREDIBLE book!!
Angela’s Ashes by Frank McCourt