What are the five most heartbreaking things that have ever happened in your fandom(s)?
1. The death of Anakin Skywalker. Yeah, I know, watched the movie a jillion times. Silly movie, silly ending, cheesy spectacular, yadda yadda yadda. It still catches me off guard sometimes, and I'll find myself with tears in my eyes while I'm either watching the movie or listening to the music. (Have you ever really listened to the music in that death scene? Very wow.)
2. The death of Chewbacca. That's not the only heartbreaking thing about it, though. It was also the way Han pushed Anakin almost completely out of his life afterwards. Chewie's death led directly to...
3. The death of Anakin Solo. Let's face it, Troy Denning didn't have the chops for writing SW, until he wrote Star by Star. This was the book that started to change that. He got a grasp on writing really emotionally draining scenes--not just Anakin's death, but Leia's reaction (and Han's reaction to Leia's reaction!). I cannot read either of those scenes without bawling.
4. The death of Jacen Solo. Yes. I'm weird. I know it. I accept it. I am one of the few EU fans who utterly, completely, absolutely, without any second thoughts, adores Jacen Solo. I mean, he's an introverted animal lover as a kid, who later turns into a free-thinking Jedi philosophy geek. (This is why I love Jacen Solo--he's me!) And then he goes and lets himself be caught, hook-line-sinker, by a two-bit wannabe Sith whore. I get why, that the whole Embrace of Pain (and everything else that happened while in Yuuzhan Vong custody) did irreparable mental damage to him. But I don't have to like it. [insert Darth Sulky temper tantrum here] This is the real tragedy, to me--that they had the chance to have a prime vector (sorry) for some pretty deep Force philosophy, and they killed him off. Jerks.
5. Darman and Etain. 'Nuff said.
(Yeah, I know, I left Mara Jade out. But I actually rather half-orphan Ben. I loved Mara, but not like I loved Jacen.)