I must say, there are a LOT of fanworks that are massive tearjerkers in this fandom. Fanart especially! As for fanfics, the four Skydancer mentioned of course. Especially Bittersweet and Party Hasn't Ended. As for the show itself, ^ this, as well as the ending of Cutie Mark Chronicles. I am a sucker for heartwarming friendshippy stuff, and the whole Spoiler: (spoiler'd in the very unlikely case nobrony has seen that episode yet) Rainbow Dash's first sonic rainboom gave the other five Elements of Harmony their cutie marks, linking them together for all those years ...manly tears, everypony. Manly. Tears.
MAJOR SPOILERS FOR MASS EFFECT 2 INCOMING... OR when Shepard dies at the end if you were a complete *** to your squad? I cried, even though I intentionally let that happen. I've never felt so sad to have such a bad-flank die on my watch. I'm never going for that ending again.
I grew up with parents that felt crying wasn't the adult thing to do. So, I tend to automatically fight any tears that start to spring up, at least for the first couple of decades of my life. In the last ten or fifteen years, I've been fighting that urge, and allowing myself to cry when I felt like it. I haven't cried over any MLP episodes, even on the third watching, but some of the stories, and pictures, and videos (in particular, the "I am a Brony" video, or whatever it's called) have moved me in that direction. Non-pony thing: The last thing I cried over was the death of Snape - both in the book and when I watched the movie.
I'm going to have to go with these guys. At the ends of both games, I got a bit emotional. It was just so well written, the fall of the Protheans, your crew's fate, it was all just so powerful, escpecially considering how much you affected the outcome. All of my crew survived (I'm always the super good guy in games), but I have seen alternate endings on YouTube, and even the paragon ending was a real tear jerker. I didn't cry myself, but as I've said before, I never seem to cry, no matter how sad I am. SO while there were no tears in my eyes, my God was I sobbing on the inside. Most of the pony stuff has yet to make me feel this way, although there have been one or two little fan fics that have been rather emotional. One that sticks in the mind is one where an age old Spike, who has protected Ponyville for centuries, reminisces about life with his friends, before joining them in heaven. I can't find the story, but I'll go hunting later. It was beautiful. ONly short, but beautiful.
Oh man, same with me. I was in the movie theater watching it. That scene was my most anticipated, so I tensed up when it got closer. I was praying that the director didn't do something dumb and change it in some way. How they did Snape's memories was so perfect that I teared up bad. The emotion in that whole scene hit me like a brick, it actually started to hurt. As for Mass Effect, I was playing the last bit of the second one. I already lost Jack to a bunch of bugs, but I didn't care about her. It was after that scene that I saw that Grunt was dying. He told me that "it was a good fight". I let out a big NOOOOOO.....
I forgot to put down a couple non-pony related things that made me a little sad, yet not teary-eyed. There both related to Pokemon actually: 1.) In the fifth Pokemon movie (Heroes: Latios & Latias), when Latios gives his life to save Alto Mare, and Latias is left all alone without her brother. My heart was in my throat at that part! 2.) In the eighth one (Lucario and the mystery of Mew), (sort of) similar situation: Lucario sacrifices himself to be with his master (sir Aaron was his name, I believe?). Again: heart in throat!
Just throwing this into the mix of "sad MLP stuff": this thing. I'd read the comic that vid is based on beforehand without crying. I felt like I was going to break down sobbing at the end of the vid. There's also Dinky Doesn't Go to School. I was crying for a good while after I had finished it. Every once in a while I thought I'd recovered, and then my brain would just yank me back in. And there was a certain, very short fan-fic posted on /co/ aeons ago that involved Pinkie Pie taking care of a deathly sick Applebloom. That was just...good lord. Personally, I'd like to go back and read it, because...for some reason, I enjoy crying (I seek out sadfics for that purpose). And that fic sure as hell made me cry. As far as inshow moments go? ...I've teared up at the second Sonic Rainboom (during the titular episode), but never the first. And that was mostly just holy expletive she did it and they're all so happy d'aaaw. And that's about it. For non-Pony related moments, there is no hell like watching the opening of Up! while trying not to cry. Which is probably why that video was so effective, given how it uses the same music.
Just search for 'Time Inception' in another tab or window. I did, and clicked on the first one. I clicked play on Time, then went to that video and clicked play, then... well, then ze magiks happened, as a certain pony would say.
I don't cry very easily, unless I'm heavily attached to the show... While watching Pokemon, I cry when I watch the episode when Ash thinks that Pikachu would be better off with the others in the forest. (the show was way better then, in my opinion) I also cried at the part in Marley and Me where ________ died. (no need for spoilers, though it's no longer new) I can't think of a sad enough moment in Friendship is Magic to make me cry yet, though... but some fan-made music videos come close to making me cry. (I, Brony and Zephyr Wind's theme are examples)
Ok. I've never really cried during a movie, but I got VERY close to shedding some manly tears in the end of Toy Story 3 and the beginning of Up. You want some movies that will tear you up? Try almost every animated Don Bluth movie and pretty much all the old school Disney Movies. The episode of Pokemon where Ash tries to release Pikachu was a tear jerker, but it was also the first episode I've ever seen. As for Marley and Me, ....I need a minute. X'( As for MLP:FIM, there are a couple of scenes that got me choked up. -When Celescia and Luna were re-united -when Pinkie's hair deflated -but for me, the one what got to me the most was at the end of the Owl episode where Twilight told Spike that he could never be replaced. I don't know why, but ever since that scene, I loved reading fanfics based on the relationship between Twilight and Spike. In fact, if I may, I'd like to post two fanfics I've read that get me choked up every time I read them based on these two.
Even though I've seen some heartwarming moments like the ones in my last post, I've honestly never started to shed tears. However, I do get lumps in my throat from time to time.