Such a big part of the series is the tragedy that occurs from simple human foolishness, and as such there are many moments sure to tug on the heartstrings.
Novel-specific entries go on their respective trope pages.
- Kiril's rendition of "Recollective Music-Box." It's easy to tell how broken he is as he describes what happened. The original detached look at Elluka's backstory is tweaked just enough to give it a very personal twist.
- Made even worse if you consider the black box at the end of Recollective Music Box and the one at the beginning of Master of the Hellish Yard to be the same as that implies Kiril crossed the Despair Event Horizon into Woobie, Destroyer of Worlds.
- At the end of the official PV for "Survival MA", he has a resigned look on his face as he prepares to kill his own sister to avenge Elluka.
- In "Whereabouts of the Miracle -Catastrophe-" Elluka wakes up to find everyone she ever knew was killed/gone.
- Meta's attempt to find redemption as a mother after a life of hurting people and being unloved in "Escape of Salmhofer the Witch," knowing that Eve Moonlit is going to screw it up.
- In fact, her entire life can be considered one big Tear Jerker. She grew up alone, without parents, fell in love with a murderer and worked for him too, then got caught when she was momentarily distracted by Eve lamenting her children's death. The man she loved made no attempts to break her out. After giving birth to the twins in Seth's experiment, she realises she was an artificial human as well and grew to love her children, hiding with them in a forest... the very forest Eve and Adam were hiding in as well.
- Despite all his crimes, many found Venomania's death, in which he struggles and fails to confess his love to Gumina in his final moments, to be very sad.
- Gumina's feelings for Venomania are further explored in her Day in the Limelight song, "The Portrait Glassred Drew", where she reveals she knew Sateriasis was really Cherubim when the spell broke. She now paints his true face just to keep remembering him, and says he'll still live in her paintings even if it's not with the appearance he'd like. She also remarks how neither she nor Cherubim realized that she loved him for who he truly was, and didn't care about his deformity. It really makes you think about what she went through—she fell in love with a dear friend, was defiled by them, and saw them die, all started by her poorly thought out plan.
- Most of the Story of Evil
Mariam: Ah, one of the Three Heroes, Mariam Phutapie, is dying betrayed by everybody.
- The separation of Riliane and Allen as children in "Servant of Evil" due to the politics of their elders, and their reunion years later.
- Allen's Twin Switch at the climax of "Servant of Evil", sacrificing himself to save Riliane from the guillotine. Even worse, the Velvet Mix PV shows her having to watch it.
- Want to make it worse? Remember, Riliane doesn't remember she has a twin when the war breaks out. The line where Allen says "It'll be fine, nobody will notice, we're twins after all" is literally the moment she realizes just who her trusted servant was... only, she has to run away right then or the plan won't work.
- Clarith's loneliness and desperation to have a friend can be pretty heartbreaking, both in the songs and in the novels.
- The ending to the song "The Maiden of the Tree ~Millennium Wiegenlied~"; Michaela dies alone, unable to confess her love to Clarith.
- The entirety of "Regret Message"
- Mariam Phutapie's death in "Retrouver of Silver." mothy even claimed he found her one of the more pitiful characters in her fate.
- Chartette's death. At this point an old woman, she confronts Abyss I.R. to take back Germaine's body, only to be swiftly defeated and burnt to a crisp. The only person who even witnessed her death was Sickle.
- In "The Daughter of Evil's" manga adaptation, we see Elluka breaking down after Annes death. Seeing Riliane cry at her mother's funeral, as well, was also quite sad.
- Ney's entire character is tragic, demonstrated by her breakdown in Praefacio. From birth she was brainwashed, experimented on and unloved, and it cracked her psyche. Exemplified by the "Story of One Girl" in the Guidebook, a small reflection on the things she could have had or been. The word "one" in the title can also be translated as "lonely."
- Gast's backstory detailed in "Daughter of Fog" too, abused by the Elphes because of his heritage and losing his little sister to poverty. This persecution led to his hatred of the Levin Church, which makes it even sadder that he was buried in a Levin graveyard. It's a Tearjerker in-universe for Yvette.
- The ending of "The Adventure of a Boy and a Girl", a poetic illustration story in the Daughter of Evil Worldguide. Most of it is happy and light, Allen and Germaine going off to rescue Chartette from bandits, bonding by talking in the forest, and Allen throwing a fit because of how easy it was. Then it suddenly flashes forward several years to the ending of Cloture Of Yellow, where Allen is on the scaffold and Germaine is the one responsible for his execution. The narrative wonders if those innocent days they had together could ever come back.
- The Master of the Courts devotion to her father. She has absolutely no idea of what she's doing and only does what her father used to do. She's naïve and has absolutely no sense of right or wrong, or even what goes on in the outside world. Even if she thinks she's heartless or lifeless, her love to her father is nothing but that, even if she's aware that she's not his true daughter and is just a doll. It's both tragic and beautiful.
- Many have found "Miniature Garden Girl" to be tearjerking for this and the ending, where the mansion burns down.
- "The Muzzle of Nemesis"; Nemesis looking back on the death of her lover.
- The entirety of "The Last Revolver" is this for the same reason, seeing Nemesis struggle with her orders and then at the last moment carry them out to extreme and instantaneous guilt.
- Somehow, the remix released for the "Muzzle of Nemesis" album makes it even sadder.
- As if Nemesis wasn't sad enough already, "And then the Girl Went Mad -End of a Moonlit Night-" is her singing about her Sanity Slippage from being abandoned, begging for the door of her house to be unlocked, and in the end wondering if her madness was her mother's intent. With only the mocking voices of Hansel and Gretel to keep her company.
- The parallels of "And then the Girl Went Mad" to "Abandoned on a moonlit night". Nemesis has nobody alive around, only the ghosts of Hansel and Gretel who haunt the house, whereas the twins at least had each other for support, and she notes how not even the moon shines on her, where the moonlight was bright enough for Hansel and Gretel that they could see the path.
- Seven Crimes And Punishments' remix of "Gift" adds a spoken line to the end, and it really illustrates that in the end, Margarita was a tragic figure who truly wanted to be loved."Come now, my prince! Let us kiss in the forest!"
- Canon or not, "The Letter She Kept Waiting For" is an emotionally grueling song, to the point that the opening instrumental alone is melancholy sounding. It depicts what mothy once planned to be the last moments of Riliane in the monastery, waiting for a sign that her sins had been forgiven and that Allen received the message she sent in "Regret Message." The orphan narrating sings about how she'll be waiting for that response until the day she dies. This does later segue into a Heartwarming Moment, however.
"We only realized her sin
- The last line of the song, due to being a Call-Back to "Regret Message":
When everything already ended..."
- The song generally considered its replacement, "Blink", is a short but poignant song depicting Riliane thinking about the future. The fact that she's worrying if her sins will ever be forgiven and that she already considers herself a monster is truly heartbreaking.
- The revelation from the very prologue of the "Seven Crimes and Punishments" album, which shows Punishment succeeded in wiping out Evillious, and now the entire Third Period is merging with the Hellish Yard. The story hasn't ended there so it's not a "Shaggy Dog" Story, but it is a hell of a punch to the reader to know that the land and its people, which we've been following since the beginning are going to come to an abrupt end someday.
- In the story itself, there's Allen breakdown in the Greed chapter, when Gallerian plans to have him relive his execution on the guillotine. He can only tremble in fear as he inwardly monologues about how scary it is and begging someone, anyone to help him. There's also how, during that time, he starts beating himself up for being so scared, saying that he hadn't changed from his days as a servant.
- The song "Drug of Gold". The fact that Carlos considers himself cowardly and blames himself for Banica's possession is just heartbreaking. Then there's also Banica's tragic childhood being mentioned in the song, and the tie-in with Banica's line towards the end: "You're running away and leaving me alone."
- Consider that Carlos said his and her feelings didn't factor at all in the decision to get them engaged, it was all the family's doing. This means that breaking off the engagement was ultimately not Carlos' decision either, and even him begging wouldn't have changed anything. In other words, Carlos is wrong when he thinks he could have changed it all if only he could have accepted Conchita back then.
- In Seven Crimes and Punishments, it's confirmed that no one who has contracted with a Demon of Sin can enter the Heavenly Yard. Consider Riliane, who repented of her ways and became devoted to the church of Levin instead. It's entirely possible that she will never see her loved ones again.
- An understated one, but in "Heartbeat Clocktower", Gear mentions the Waiter "indulging in selfishness whilst showing sadness at the loss of her 'other half'".
- In a way, the otherwise Nightmare Fuel song "Full Moon Laboratory" qualifies. All the singer wants is to bring back her creator, who abandoned her in the lab.
- The death of Ma in the end - not that she didn't deserve to be punished, but in the end, the audience and the cast learns that all Ma really wanted was to exist, and to confirm her own existence like literally everyone else in the world could. Ultimately she's denied her wish, as her process for confirming her own existence meant the world would end. It's even more bittersweet when she dies because, as she was in Nemesis' body, her death means the extinction of the (living) human race. Her status as the sole member of the cast to cease to exist upon death instead of passing on to the afterlife or being reincarnated can earn her some pity as well.
- The Court Ending. Irina, Adam, Eve, and even Gammon are caught in its reformatting, and are forced to replay the whole Evillious timeline in a repeating loop, forever. Not only that, Irina incarnates as Maria Moonlit/Alice Merry-Go-Round, and gives birth to twins, but a virgin pregnancy is seen as suspicious by the Senate, so she puts them in a river, but one of them dies. All because Irina wanted kids.
- Michelle's fate. After dying, she makes a contract with Eve Moonlit to work together with Gallerian to create a utopia. Acting with Eve's personality, Michelle often forgot who she was, and her Gift was sometimes too strong that she almost lost her heart to Eve multiple times. Then, she is sucked into the Clockworker's Doll by Hansel, then released to help Gallerian in the Hellish Yard. Michelle from then on is treated as the Sloth Sinner. It's a sharp contrast to the bright and kind young girl in Judgment.
- Irina's fate as a whole can also be counted as this. She was one of Ma's three souls, then incarnated as the "Doll Director" (later becoming the Master of the Court). She couldn't do much under Gallerian's care, entirely reliant on him to even move. She seems to be happy to have him as a father, but it's clear she's aware he only loves her because he thinks she's Michelle. After being taken to the theater to be safe, she's summoned by Adam back to Gallerian's mansion during their argument, and as a result not only has to watch Gallerian die but also gets burned by building burning down. Ma herself notes that Irina's devotion to her "friends" in the theater is a result of terrible loneliness, and the fact that she gives birth to the Irregular twins right before the world ends doesn't help. She tries to revive the world after the fact, but as a result is reformatted into the Court Ending as Maria Moonlit, being forced to go through the entire Evillious timeline forever. This is a very, very sharp contrast to what she was able to do as the "Red Cat Mage," being able to orchestrate the Venomania Event AND the whole of Story of Evil. Karma bit her very, very hard.
- When Nemesis fires at the Black Box in the song version of master of the heavenly yard, the song wonders who she's "thinking of" as she watches the fireworks produced from the explosion. We, of course, realize that she's thinking of Nyoze, a callback to The Last Revolver. For bonus points, the image of Nemesis shooting the Black Box has her surrounded by sakura petals, like how she met Nyoze under the sakura tree.
- Though Kiril ultimately regains his sanity and is reunited with the real Elluka, he still ends up losing Irina.
- The ending to this MMD version of "Servant of Evil". At the execution, Allen looks out to the crowd to see Riliane. She looks at him and then puts on a happy face, just so that Allen can see her smile one last time. He smiles back just before the blade descends on his neck.
- This fanmade PV for "Regret Message" has a moment from 2:30 to 2:46 showing a montage of characters' losses. Clarith loses Michaela, Elluka loses Leonhart and Mariam, Germaine loses Leonhart and Riliane loses Allen.
- Then there's this one fandub video for "Regret Message." Listening to Riliane sobbing helplessly as she begs God to give her and her brother one more chance to be happy together in another life, now that she's finally realized what a horrible monster she's been, just... Gah.