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Tear Jerker: Redwall
The series in general / Meta examples
Author Existence Failure left dozens of people across the internet weeping, even those who hadn't read the books in years.
There's a subdued one in this book where Martin and company find a dead, elderly searat near his camp on the beach. Their first response is to speak to him respectfully while trying to help him; after they realize he's gone, they give him a proper burial before making use of his shelter and supplies. This is very sad in its own right, but when one takes into account the later books' stock response to a vermin death — save your tears, that one won't be hurting anyone else — it's absolutely heartwrenching.
The hares of the Long Patrol have a heroic last stand to help the prisoners they've rescued from sea rats escape. Even if Hon Rosie survives, it's still heart wrenching: "My running days are over." "Hate to remind you, old thing, but we didn't come here to run."
Spriggat the hedgehog's death. Especially what Samkin says: "He told me he was going to find a green forest filed with flying insects and then he smiled and... oh, my poor old friend...!"
Urthstripe's entire life story. First his parents are killed and he is separated from his brother at birth, then his stepdaughter runs away leaving him thinking she hated him, then just as he is about to be reunited with his family he kills himself along with the Big Bad Feragho.
Burrley the mole's death, his nephew's reaction, and Thrugann's subsequent words of comfort — "There there. Hushabye, mole. Nuncle Burrley's gone away, but you'll see him again some sunny season." It's both heart-breaking and completely heart-warming.
"Whurr be moi ol' nuncle Burrley? Burrhurrhurrhurr..."
Really, Salamandastron is in many ways the saddest book in the entire series. More named characters die in it than in probably any other book.
Also, think about it: Polleekin knew. She said that a bad fate would befall them if they were to return to Marshank, but she refused to say what in case she was wrong. Still, they left with every intention of going back there, and that makes Rose's last song to Polleekin especially sad.
Goodbye, my friend, and thank you, thank you, thank you It makes me sad to leave you upon this summer day. Don't shed a tear or cry now, goodbye now, goodbye now, I'm sure I'll see you somehow if I pass by this way. For the seasons don't fortell Who must stay or say farewell And I must find out what lies beyond this place. But I know deep in my heart We are never far apart While I have a memory of your smiling face. Goodbye, my friend, and thank you, thank you, thank you Your kindness guides me ever as I go on my way.
Felldoh's death. He goes down fighting, beating Badrang up first, and then after Badrang calls upon a dozen of his horde to help, Felldoh takes several with him. After he dies, his friends honor him yet at the same time admit what he did was foolish. Though if Badrang had kept his promise to fight him one-on-one, Felldoh would have easily killed him and ended the book 10 chapters early.
The orphans on the island in The Bellmaker, the two youngest still waiting for their caregiver to Please Wake Up.
Mellus' funeral and Blaggut's return immediately thereafter.
Finbarr sails off on the calm sea...
Outcast of Redwall
Skarlath's death, full stop. For bonus points, there's an excruciatingly long build-up as Nightshade prepares to shoot him.
Then there's the bit where Sunflash has to explain to his adoptive family that Skarlath won't be coming home.
Veil's storyline in general is tragic. His mother is dead, his father abandoned him in a ditch, and most at Redwall write him off as a lost cause from the moment he arrives. His reaction to his banishment is especially saddening: "I've got no family, I'm alone. What will I do?" He did bring it on himself, but given his life, he's still pitiable. There's also the way he adopts "the Outcast" as his title, as if it was his destiny.
And then of course, there's his Redemption Equals Death moment. "Go away... let me sleep!" Between this moment and the aforementioned death, the climax of Outcast is one big Tear Jerker.
The Pearls of Lutra
When Piknim is brutally murdered by jackdaws. Even worse since she wasn't a warrior, just a simple mousemaid, and Jacques spent a lot of time fleshing her character out and making the reader love her, which makes the event itself all the more saddening.
Legend of Luke
Part 2. Possibly the only real tragedy in the series.
Martin speaking to his deceased father.
Cregga's death, especially coupled with the dying visions she has of her old Long Patrol and the song of a triumphant, long-gone battle that's being sung at the time.
Rillflag's death and Deyna's kidnapping. this was just outright tragic. Imagine you just met your baby brother, your father takes him into the woods. Never returns, you assume both are dead (For the equivalent of 15 years) The fact that Mhera and Filorn cried for a week straight. You would have to have a heart made of solid ice not to cry reading those chapters.
Shogg's death. Made worse by the fact that he died trying to kill an adder that Triss or Sagax could've easily defeated on their own...
Bragoon and Saro'sHeroic Sacrifice. Even more depressing by the fact the quest they died for was completely pointless at the end
Globby's death. Brat or no, he was basically just a messed up, hungry kid. After his failed escape attempt leaves him cornered in the attic, terrified of the Redwallers who've been beating and threatening him, he breaks down and sobs. After dying gruesomely, he goes completely unmourned.