I thought I'd do a couple of recs, but instead of fic recs I'll do actual book recs. And the theme is "books that make me cry". Please note that this is a selective list and doesn't include every book that ever made me cry. (The Stand did. The Outsiders used to, but doesn't anymore.)
My Nightingale is Singing by Astrid Lindgren
Yes, I'm the one who wrote the review at amazon.com. What can I say, it's a good book and people deserve to know.
Astrid Lindgren is mostly known for her Pippi Longstocking books. This story is not like them, and it's best to be prepared for that. Instead of humour and rebellion, we have the bleak life of an orphaned, penniless child in 19th century Sweden. Malin/Maria wants to have something that's beautiful, and at long last she manages to get it, but her sacrifice is very dear. For her, it's a happy ending; for everyone else it's a cry-your-eyes-out.
The Emperor of Portugallia by Selma Lagerlöf
Continuing with another Swedish book, this one is a little bit harder to get hold of (it wasn't available at amazon.com), but it shouldn't be impossible - large libraries will certainly have it.
The book tells a story of (paternal) love and of madness. A father can't stand it when he finds out that his beloved daughter is a prostitute, and goes mad, convincing himself that she's an empress in disguise. It's told entirely from his perspective, which might be jarring for some, and even more if you're not used to the magical realism of the old Swedish countryside (the existence of trolls and fairies are taken for granted). But it's a truly fabulous story and it gets me in tears every time.
The Emigrants (with sequels) by Vilhelm Moberg
Yes, yet another Swedish book. This is the last one, I promise!
Actually, I'm cheating, because this is not a book but a series of four books, each one pretty thick. But if you like to weep and like epic stories, this is a given. It's the story of a few Swedish families emigrating to America, and it shows all their joys and hardships during the years. Reasons to cry will come in all the books, but perhaps above all the third and fourth ones. Things are better for them in America, but that doesn't mean they're good.
In Sweden, these books are so classic they're cliché, and they have also been made into two movies and a musical (by Björn & Benny from ABBA). So reading them is not only a joy for the wannabe weeper, it's culturally enhancing as well.
Pinquo by Colin Thiele
Finally leaving Sweden and heading for Australia, this is the tearjerker for me. Granted, I was seven when I first read it, but for a long time it was the only book that made me cry, and that means something. (And for some bizarre reason, Amazon doesn't have it, though it's available in other places. Again, try a library.)
Like "Love Story", this book explains right from the beginning that the main character is going to die by the end, and yet makes you cry once it happens. Of course, it helps that the main character in this book is a penguin - I've always loved penguins. And no, this isn't a story of anthropomorphic talking animals. It's about ordinary penguins, and sadly their circumstances are far too ordinary as well.
And finally, there's
Seven Little Australians by Ethel Turner.
It's sentimental. It's old-fashioned. It's just the slightest bit silly. But for being what it is, it's very charming. The siblings are drawn very realistically compared to many other books of the time. And the high-spirited Judy is quite wonderful.
As a child, I lived with these children, and there's one chapter that can still make me cry even if I just open the book and read that one chapter without reading the stuff that comes before and after.
This one isn't available through Amazon either, except in what appears to be an extremely shortened version, but it is available as a download, so you have no excuse not to read it. Go click on the link. Pretend it's fanfic. :-)