The first episode of an audio adaptation of the Pony POV Series manages to make Applejack's Discording (from her perspective) even more of a Tear Jerker thanks to the music and just how absolutely broken the voice actress makes her sound!
The Eventual Goodbye. Basically in a nutshell, Twilight believes that all will last forever with Spike and then she thinks on it some more as Spike starts to grow into an adult dragon and in turn, Twilight has to say goodbye to him forever. Sure it's all sketches, but it's nicely done that will leave many manly tears behind at the sentimental value of what could possibly happen in the end. And the music that's played the entire time doesn't help matters either. Very sad indeed.
This flash video starring a down on her luck Trixie who has essentially hit rock bottom. The music goes perfectly with the video as well. Though it ends on a Heartwarming Moment, thanks to what seems to be Luna.
Derpy's Censored. Part of it is the actress' very real sorrow, and part of it is thanks to a spot-on Meaningful Echo: "I just don't know what went wrong..." Added to how it's performed by who is considered to be the de facto Fanon!Derpy voice actress!
It's funny how peple considered the character so very insulting and upsetting because of how her name could be interpreted, yet none of these people seem to notice how a lot of her fans were choosing to interpret it. Say what you like about the reactions to the changes (like all fandoms, we have our own bucket full of crazy who went over the top about it), but the fans weren't using the word 'Derp' as an insult. Balddumborat's pain is as real as any of the insulted parties. Not only did we have a chance to portray a disabled character in the media instead of locking them away like disability is shameful, but we had a chance to completely change the meaning of a word amongst a huge circle of people, and make it so that when people heard the word 'derp' they thought of something cute and friendly and kind rather than something hurtful. There's another Tear Jerker right there.
Now is animated to be even more gut wrenching! Especially when you listen closely, and in the background is the music from the Dead Island premiere trailer.
"The First of a Thousand Lonely Winters" Really drives home how painful it was for Celestia to banish Luna, even for the sake of Equestria. The abrupt end of the flashback, timed with the music, is particularly heart-breaking.
This PMV. Seeing ponies attempting and failing to face their greatest fears is just heartbreaking.
This video which acts as an origin story for King Sombra. In that video, he once started out as a kind-hearted unicorn who gave into the darkness in his heart. To make it worse, he had a friend whom he enslaved.
This crossover with Amnesia: The Dark Descent has a mix of this and Nightmare Fuel when Twilight wanders through a mansion and hears Fluttershy crying. She looks for her and asks if something's wrong. As Fluttershy reveals herself, she shows Twilight that something is wrong...very, VERY wrong. Twilight's reaction is heartbreaking.