Hmmm... Gonna be a tough list for me... To keep short!
First movie I ever cried over: Baby, Secret of the Lost Legend. I was probably 5 or 6 when I watched it with my sister. The scene where they shot the mommy dinosaur. I ran up stairs to my mom screaming and bawling my eyes out. My sister got yelled out cuz of it. She was like, "What the fuck was I supposed to do? How was I supposed to know he'd act like that?" I remember that pretty well.
Most of my crying movies were tears of joy, so it makes it hard to list. I'm super emotional though.
42 was the most recent. The Jackie Robinson movie that just came out. I didn't expect to get so emotional from it, but I did.
Wreck-It Ralph.
Up.
Toy Story 3.
Wall-E. (not sad tears, cute tears)
An American Tail.
The Land Before Time.
All Dogs Go To Heaven.
Plague Dogs.
When The Wind Blows.
Children Who Chase Lost Voices.
Voices of a Distant Star.
5cm per Second. (although it's too boring to watch again)
The Girl Who Leapt Through Time.
Pan's Labyrinth.
Edward Scissorhands. (still to this day)
The Lion King.
Dumbo. (no Bambi on this list, I don't even remember that movie)
Casper.
Flight of the Navigator.
Old Yeller.
Grave of the Fireflies.
Pom Poko.
Whispers of the Heart.
Princess Mononoke.
Forrest Gump. (that ending... omg that ending)
Finding Neverland.
Seven Samurai.
Ikiru. (Akira Kurosawa film about an old man with stomach cancer)
Titanic.
Batteries Not Included.
Short Circuit.
Bridge to Terabithia.
Little Women.
Jack.
Patch Adams.
Empire of the Sun.
Inception. (omg that movie fucked me up for a week hardcore)
Eternal Sunshine of the Sleepless Mind.
City of Angels.
The Crucible. (that ending was so depressing)
Slayers The Motion Picture (one of the tears of joy cases)
Super Ultra Brothers 8 (another joy one, tinged with nostalgia)
Magical Twilight. (yes, I included hentai in this list)
Rurouni Kenshin. (the first OVA)
Pokemon The First Movie. (pika...
)
Then there are the TV shows. Far too many to count for me.
Ultraman Tiga (Obiko, and the episode where Garote kills the nurse's fiance)
Ultraman Mebius (the episode Mirai says goodbye, and Ultraman 80's cameo)
Full Metal Alchemist.
Ayakashi & Mononoke (both bakeneko episodes, especially Mononoke's)
Angelic Layer.
Magic Knight Rayearth.
Card Captor Sakura.
Irresponsible Captain Tylor (omg the episode when the retired admiral dies had me bawling)
Great Teacher Onizuka. (the live action)
Serial Experiment Lain (fucking depressed the shit out of me)
Vampire Princess Miyu.
Bokurano.
Cowboy Bebop.
Chobits. (the book with the bunny)
Mr. Belvedere. (the episode where the old man dies on the Boardwalk)
Punky Brewster (can't remember the episode)
Children's Toy.
Chrono Crusade. (disliked the show, but wow that ending...)
Rurouni Kenshin. (the show)
And a couple games.
Shining Holy Ark.
GeGeGe no Kitaro GBA. (the ending is kinda sad)
Final Fantasy VI.
Terranigma.
Grandia.
Sakura Wars. (I think it made me cry)
True Love. (yes, I included a hentai game too)
And the only books to ever really make me cry:
The Velveteen Rabbit.
Of Mice And Men.
Tortilla Flat.
The Pearl.
I know there's something I'm missing. Really missing. I have some things on my CDRs that I kept because they made me cry so much. But what also makes it hard for me to list things is some just make me cry because they make me so nostalgic -- it's not the movies or shows themselves, but the memories associated with them. One of my former coworkers told me I should see Amelie, but I haven't gotten around to it yet.