1. Tara Maclay (Buffy the Vampire Slayer) 20th Television "Your shirt." It's hard to believe a witch as powerful as Tara would have such meaningless final words. And yet, when Warren fires shots at Buffy, killing Willow's girlfriend in the process, Tara has no time to register her injury before she's gone. 2. Jason Todd (Batman: A Death in the Family) DC The cruelest thing about the death of Jason Todd, Batman's then Robin? It was voted on by fans. There was actually a 900 number where readers could vote for or against Jason's death — and we know how that turned out. 3. Jin-Soo Kwon and Sun-Hwa Kwon (Lost) ABC There were so many deaths on Lost it's hard to pinpoint the most heartbreaking. But Jin and Sun are top contenders — finally reunited after so much time apart, they drown together, holding hands until the very last moment. 4. Boromir (The Lord of the Rings) New Line Cinema Boromir doesn't exactly end on a high note, as he fights with Frodo for the one ring. But his heart is in the right place, and the rest of the fellowship mourn their former companion's death after he's struck repeatedly with arrows. 5. Optimus Prime (The Transformers: The Movie) Long before the Michael Bay movies sullied the franchise, the original 1986 Transformers traumatized kids everywhere when it killed off everyone's favorite character Optimus Prime. But he's wounded in battle against Megatron, so at least he dies a hero. 6. Fred Weasley (Harry Potter and the Deathly Hallows) Warner Bros. Harry Potter fans stayed up all night reading the final installment of J.K. Rowling's series, hoping that their favorite characters would survive the final battle. Alas, the good guys soon dropped like flies, and Fred left his poor twin brother behind. 7. Yoda (Star Wars Episode VI: Return of the Jedi) 20th Century Fox After being such a pivotal figure in The Empire Strikes Back, Yoda dies rather quietly in Return of the Jedi. It's not a tragic death in the sense that he seems to have chosen it for himself, but it also feels sudden — and Luke has more to learn. 8. Alexandra DeWitt (Green Lantern) DC Alex's death isn't pretty — strangled by Major Force and stuffed in a refrigerator. In fact, the brutality of her murder, coupled with the treatment of other female characters in comics, inspired the phrase Women in Refrigerators. 9. Rue (The Hunger Games) Lionsgate A whole lot of kids die in The Hunger Games — it's pretty awful all-around. Still, there's something particularly heartbreaking about Rue's death. She's such an innocent that it's inevitable, but that doesn't make it sting any less. 10. Captain America (The Death of Captain America) DC Is anyone in comics ever really dead? And yet, Captain America's assassination resonates for quite some time, as Tony Stark and Black Widow go off in search of their friend's killer, and Bucky Barnes plans his revenge on Tony Stark for the Civil War. 11. Fred Burkle (Angel) 20th Television Famous (and horrible) last words: "Why can't I stay?" If Angel had continued past its fifth season, they might have found a way to bring Fred back. Illyria did retain her memories, after all. As it stands, her death in Wesley's arms feels final. 12. Jake Chambers (The Dark Tower) As if dying once weren't bad enough. When Jake fell, uttering the iconic "Go then, there are other worlds than these," it was clear he'd be back. And he did last for a while, eventually sacrificing himself to save Stephen King. (Yes, the very author who chose to kill him off.) 13. Artax (The Neverending Story) Warner Bros. How many childhoods were destroyed when Atreyu's loyal horse Artax succumbed to despair in the Swamps of Sadness? It's almost too painful to think about. Just try to look at that horse's face without breaking into Bastian-like sobs. 14. Boy Blue (Fables) Vertigo One of the saddest things about Boy Blue's death is that he's ostensibly not coming back — unlike the other fairy tale characters in Fables, he's just not popular enough among the mainstream to live on. And that's tragic, because he proved himself to be a noble hero in the end. 15. Ned Stark (Game of Thrones) HBO After Joffrey promises mercy, Sansa has to watch her future husband order the beheading of her father. The Starks don't have the best of luck, as it turns out. And if you think Ned's death is awful, remember the Red Wedding. 16. Seymour (Futurama) 20th Television Look, it's just sadder when dogs die. Especially a dog like Seymour, who waits for Fry for years after his disappearance. Their near-reunion is aborted at the last minute — and the less said about it the better, unless everyone wants to start crying. 17. Spock (Star Trek II: The Wrath of Khan) Paramount Pictures Star Trek III: The Search for Spock kind of spoils the fact that Spock's death isn't permanent, but it's still hard to watch. With his best friend Kirk watching, Spock sacrifices himself by enduring deadly levels of radiation. "Live long and prosper" never felt so melancholy. 18. Ianto Jones (Torchwood) BBC As sad as Ianto's death is on its own, it's even sadder for the way it breaks up the Jack/Ianto relationship. And the shippers were not happy about it, especially since there are so few good (and yes, hot) LGBT pairings on TV. 19. Wash (Serenity) Universal Pictures Damn you, Joss Whedon. How many deaths on this list fall squarely on your shoulders! Like so many Whedon casualties, Wash's departure was nasty, brutish, and short. It was so fast that we were forced to mourn later, in the privacy of our homes. 20. Rorschach (Watchmen) DC Rorschach isn't an easy character to like, and yet, his death makes an impression. Perhaps it's the fact that the secret of Ozymandias' plot dies with him — he dies because he's unable to sacrifice his ideals, while the others move on with their lives. 21. Data (Star Trek: Nemesis) Paramount Pictures A character as iconic as Data deserves a better exit than this — though since Brent Spiner is credited with writing this story, that must be the way he wanted it. And yes, some form of Data returns with B-4, but it's just not the same. 22. Agent 355 (Y: The Last Man) Vertigo Few comic series pack the emotional punch that Y: The Last Man does. And of course, it's when Yorick and Agent 355 finally confess their feelings for one another that she gets killed by Alter. These deaths always happen when they hurt us the most. 23. Alaric Saltzman (The Vampire Diaries) The CW He's evil and then he's not evil and then he's dead. It's a lot to process. And in typical Vampire Diaries fashion, Alaric still pops up from time to time to remind us how much we miss him — and how much Damon needs him — before spiriting away again. 24. Newt and Corporal Dwayne Hicks (Alien 3) 20th Century Fox We don't see Newt and Hicks die, but that's a small consolation. Two of the most principle characters in Aliens — including the girl Ripley spent most of the film trying to protect — are dead before the third movie even begins. It's just cruel. 25. Gwen Stacy (Spider-Man) Marvel And this is why you should never date a superhero. Gwen Stacy's death is common knowledge among comic fans. Casual moviegoers will likely soon learn of her fate, as it looks like The Amazing Spider-Man 2 is headed in that direction.