Black Butler is filled with tearjerking moments and downer scenes.
[[folder:Red Butler Arc]]
* Madame Red's death at the chainsaw of Grell, and Ciel's reaction. "Red is... your favorite color".
** Bonus in that Grell killed her because she refused to kill her beloved nephew.
** Her horrific backstory as well. Yikes.
** From the Alice in Wonderland OVA, Madam Red played the Queen of Hearts and after the trial Sebastian saves Ciel from being beheaded. Suddenly, Madam Red is wearing her normal clothes and smiles sadly. And then, to twist the knife further, she says this:
-->"So, you're going home. I hope we can meet again in another dream."
* Madame Red's funeral. Ciel placing the dress on her corpse is an "aww" moment.
* It could be considered a borderline tearjerker when Agni refers to Sebastian as his friend. His genuine surprise that he would label him as such may indicate that Sebastian has never had a friend before (his being a demon aside) and is happy to be considered one. Life as a demon may be lonely for Sebastian.
* In the manga, "Would you like an orange, sir?" said the poor little girl with freckles. After a particularly nasty moment, Ciel's grasps at redemption were hopelessly despairing to see.
* The ''entirety'' of the story revolving around the Noah's Arc Circus. Especially [[spoiler: Doll's death.]]
** Special mentioning should go to Snake. He spent his young life being used as a sideshow attraction and mocked for his appearance. One day, the circus troupe found him and took him in, treating him like family. Then during one mission, they all go missing and never come back. Snake searches for weeks, and finally finds Ciel, who he correctly deduces was involve with their disappearance. [[BlatantLies Ciel tells him he had nothing to do with it, and will help Snake find them.]] He takes Snake on as his new footman, and the other staff gladly take him in. After a while, Snake is as loyal to Ciel as the others.
*** It might not be as bad for those who believe the theory that Ciel lied and took Snake in because he was still torn up inside with guilt over [[spoiler: killing Doll/Freckles]].
[[folder:Phantomhive Manor Murders Arc]]
* The scene in Chapter 41 where Ciel straddles Sebastian's supposedly dead body, buries his face in Sebastian's throat and insists his butler was never to leave his side is comparable to a boy mourning his beloved dead dog. [[spoiler: Negated in that he knew Sebastian was alive and was just passing along orders for their plan.]]
* In chapter 44, watching Mey-Rin and Finnian's breakdowns after it seems to seriously and completely dawn on them that Sebastian is dead is utterly shattering Luckily, Sebastian is not really dead.
[[folder:Luxury Liner Arc]]
* Chapter 57. Elizabeth is about to be seemingly killed by a horde of zombies. "I wanted you to think I was cute, up until the end..." Cut to shot of Ciel's anguished face.
* Elizabeth's backstory in chapter 58. At first, we see her as a genius at fencing, but Ciel doesn't know that and is happy to marry just plain sweet Elizabeth, and she promises to be a wife he can protect. Then when Ciel returns with Sebastian and she realizes she's now taller than him, she wishes to be a wife to protect him.
* During Elizabeth's flashbacks in [[http://www.kuroshitsujimanga.com/58/08/ chapter 58]], her mother slaps her when she complains about having to fence wasn't "cute". Cue a combination between a tearjerking and heartwarming moment between mother and daughter. It goes to show that Francis, despite all of her cold aloofness towards her family, she truly does care for them and seems to want to protect her daughter and Ciel in any way possible given the Phantomhives' unfortunate profession.
--->Elizabeth: I don't want to practice the sword anymore! Swords aren't cute at all!
--->Francis: I know it's hard, but it's for his sake and yours. You understand, don't you?
* Chapter 61. When Sebastian is stabbed by the Undertaker; especially when Sebastian reaches out to grab Ciel's hand, but then gets a giant death scythe through his body. Cue the beginning of a dramatic flashback.
* Depending on your point of view, any scene which shows the deep trust and appreciation the servants of the Phantomhive household have for Sebastian (or Ciel, again depending on your point of view) can be soul wrenching to know that the person/people they care about is nothing more then an illusion created to manipulate them. The same goes for anybody who befriends Ciel while he's undercover- namely Doll, since she trusted him deeply and learns the truth in the worst way possible.
** One chapter revealed that after Sebastian saved Ciel from the kidnappers, they arrived at the hospital Tanaka happened to be at for his stab wounds. Tanaka, at the sight of Ciel, stands up ''out of his wheelchair'' because he's so happy to see him alive. That, and the end of the murder mystery arc when Tanaka gives Sebastian the pin back, saying he is the rightful bearer of it. If only he knew...
[[folder:Emerald Witch Arc]]
* The end of Chapter 91: Ciel sobbing his eyes out and telling Finnian he isn't worth protecting.
* Crosses with NightmareFuel, but the cliffhanger of Ch. 94 when Sebastian is about to devour Ciel's soul while he was in the middle of a HeroicBSOD, complete with him pretty much calling the boy a waste of time. He didn't since Ciel snapped out in time, but this still serves as a grave reminder that Sebastian only sees Ciel as a meal and of what could easily happen if the boy either gives up on his revenge or even changes in a way Sebastian does not like.
* For all of the things that happened, you have to feel at least a little sorry for Wolfram when he sees that Sieglinde hates him after she found out the truth. Just look at his expression when she calls him a liar! Anybody can see that he truly does care for Sieglinde, down to being shameful and repentant for having to break her legs himself, most likely against his will. However, Hilde Dickhaut (who's actually the Major of her troupe) reminds him that he has his "duties" - To kill Sieglinde if she ever found the truth and tried to run away. Wow...that's hard. But seeing all of his time together with Sieglinde, not to mention traces of hesitation towards his colleagues, one might bet that he would eventually go against her and join Ciel's group.
** There's good news and bad news: Wolfram was able to save Sieglinde by shooting down Grethe before she could kill her/the other servants, but he was ultimately killed by a shot in the back by Hilda. Judging by Sieglinde's reaction, she most likely accepted his apology or at least still has some non-hateful feelings left for him intact.
** However, the next chapter reveals he was saved because Ciel needed someone to look after Sieglinde.
* Put yourself in Sieglinde's shoes for a second...Actually, don't. She has lived her whole life with the women of the village within the forest,only for everything to be a lie because her mother, the old and disfigured women, saw that she was a child genius. She had her feet bound and worked meticulously on the magic to rid the village of the werewolves, all because her mother wanted her daughter to develop the poison. The old woman had isolated Sieglinde from the world, took away entertainment, and created an imaginary world, all simply because Sieglinde had happened to be born a child prodigy. Ciel's reaction in chapter 98 says it best:
---> Ciel: You ruin a child's feet and threaten her to develop a weapon...Is that what a mother would do? Children are not their parents' tools!
** And to top it off, after everything has crashed all around her, the boy that she viewed as her first outside friend basically tells her that her life is worthless, it will never get better, and that she should just die...while holding a gun to her forehead, no less. And even though the following chapter shows that he was really convincing her to live rather than accept death, the only reason he did that was because he was given an order to bring her to a monarch who could very well be planning on using her for reasons similar to her mother.
* Chapter 105 drops a major one for the Shinigami in general. As it turns out, all of the Shinigami were once regular humans who were DrivenToSuicide and are now being punished by being forced to face death daily by reaping souls until they have been forgiven. It also gets worse; considering that the German reaper Sascha is noticeably younger than the other reapers, it's implied that this fate also applies to young teens/children who killed themselves.
* Undertaker crying over Vincent Phantomhive's death, along with the implication that Diederich began overeating/no longer visited England because Vincent is gone.
* Even though it was probably for the best, Ciel telling Sieglinde to view everyone and himself as the enemy out to use her and that she must use others to survive has a tinge of sadness to it.
** In the same chapter there is Victoria's comment to Ciel on how he is becoming so much like Vincent along with how Ciel momentarily reacted to it, though this also crosses into NightmareFuel for those who saw this as Victoria threatening Ciel...
[[folder:Blue Cult Arc]]
* Lizzie's words to a sleeping Ciel in Ch. 113:
--->'''Lizzie:''' I'm sorry...[[spoiler:''I can't save you.'']]
** Lizzie's current situation: [[spoiler: she has become involved with Bravat's cult after he gave her some sort of information regarding Ciel. Even after Sebastian was able to bring her home (knocking her out after she attacked him) she wound up escaping and returning. Also, ever since joining the cult she has been portrayed as solemn and nearly broken, a complete 180 from who she used to be.]]
* Ciel coldly admitting that he never viewed Soma as a friend and instead just a simple piece to utilize just like everyone else, adding that if Agni refuses to let Ciel use Soma the Indian duo should leave since they have no further business in England.
* Ch.127 continues from the previous chapter of [[spoiler: Soma and Agni being ambushed from a mysterious attacker. After being wounded multiple times, Agni throws Soma into a room and [[HeroicSacrifice holds the door locked as he is stabbed to death.]] ]]
** What makes this all the more heart-wrenching is that [[spoiler: despite bleeding and having lost his right eye, Agni still has the strength to place Soma in a room to be safe, all while giving a thank you for Soma in his mind and hopes that Soma could always be the same sun that shone for him, smiles at him despite the fact that he knows he's going to die, and the final page with them depicts Soma screaming and crying for Agni, and Agni holding onto the door resigned to his fate. When Sebastian and Ciel show up scenes later, they find Agni still at the door ''seven knives'' stabbing him through the back, but his hand still gripped on the door all while Soma is crying.]] Someone ''please'' give this Indian prince a hug.
* Ch. 128, continues from the previous chapter when Ciel approach traumatized Soma, [[spoiler:He punched Ciel in a tearful blinded by rage toward him.]] You can tell Soma is suffering afterwards. [[spoiler: It implied that he blames him for Agni's death.]]
** Ciel [[spoiler: putting the blame for Agni's death on Soma since he wouldn't stay out of his business,]] all the while it looks like he's either about to cry or panic.
* Also in 128, how Grell [[spoiler: confirms Agni's death]] has a very rubbing-salt-in-the-wounds vibe to it, especially given her smug demeanor, dismissal of his remarks, and reminding the viewers that, as said earlier, we were going to see her soon.
* Ch. 130, as has been long suspected it was confirmed that [[spoiler: the Two Ciels Theory was correct and Our Ciel has a twin brother who is the real Ciel Phantomhive. Our Ciel's reaction is quite upsetting as he hardly speaks at all (quite uncharacteristic for him) whilst his brother speaks down to him.]]
** This is made worse by [[spoiler: Our Ciel referring to himself as an "extra", less important than his brother.]]
* As heartwarming as it is, Ch. 131 and onward that depicts [[spoiler: the Phantomhive twins as happy and loving toward each other]] doubles as this ''big time'' of the HarsherInHindsight variety.
* In the anime, Ciel appears downright cruel and malicious at times, although in the manga, he is simply bitingly icy and elitist. It's eventually revealed that he was a happy, loving and carefree child, though sickly and shy. Then his parents (and pet) were murdered, their mansion set on fire, and he was kidnapped. He was locked in a cage with other children his age to be a child sacrifice until he called upon a demon in his desperation to live. He shortly after unleashes terrible revenge on those who he felt wronged and humiliated him. ''All before turning eleven.''
** A particular moment in the manga triggers Ciel to suffer an intensely brutal [[http://en.wikipedia.org/wiki/Posttraumatic_stress_disorder PTSD]] attack. Heartbreaking stuff.
* The deaths of Lau and Abberline in episode 20. Though Lau comes back somehow in the second season.
** Maria, Abberline's to-be wife, reads about his death and receives merely a handful of toys as compensation.
* Finnian's very harsh backstory. It depicts him in a room with a barred window with sunlight and a little bird chirping before flying off..cue him on a dissection table with a syringe going in him as he screams and cries and ''begs'' for the people to not hurt him. Then he runs off and bumps into Sebastian and he, for the first time in his life, is actually surprised that him rushing into Sebastian didn't hurt him. Even if he doesn't know that Sebastian is a demon, he looks so relieved that he's not considered a monster for those horrible treatments.
* The house servants having to put down poor Pluto.
* Episode's 7 and 8 of the second season in which Alois, who before seemed like a complete jackass, is stabbed and ignored by Claude for a bit who's busy practically orgasming over the taste of Ciel's blood. Alois's tearful response "Oh, you look like you've seen a bunch of maggots squirming in a dung pile" to Claude's indifference towards him, we learn his backstory where his little brother died and left him alone, and he practically confesses his love for Claude, telling him he's the only one he has left in the world, before Claude tenderly holds his face and stabs him to death.
** Made even worse due to the ending song for episode eight, Kagayaku Sora no Shijima ni wa. If the song itself isn't sad enough, there are always the visuals. Remember the shot of Luka running to hug Alois from behind?
* In Episode 11 of second season, Alois (in Ciel's Body) asks Hannah to tell him that she loves him and give him a hug, which he's ALWAYS NEEDED. She does both, which prompts him to cry tears of joy and say "Love is...warm, isn't it?" Pass the tissues please.
* The final episode of anime season 2 which is either a BittersweetEnding or an outright DownerEnding, possibly both.
* From the live-action movie:
** Ciel lost his parents at the age of 10. Shiori watched her parents die at the age of SEVEN and then who knows what happened to her before she made the contract. And the aunt who raised Shiori? She helped the perpetrators and even watched as the event occurred.
*** Said aunt was driven to that action because of a situation that mirrors Madam Red's but manages to be worse. Hanae was married to Shiori's father until she got into an accident that caused a miscarriage/rendered her barren. However, not only does he coldly divorced her for it, he then goes on to marry her own sister/Shiori's mother.
** If the movie is considered as canon and if what Hanae says is true, then since Ciel, there's been an ongoing curse-like cycle where every head of the Phantomhive/Genpo family, possibly including Shiori's father, has been in similar tragic situations where they were pretty much forced to sell their soul to Sebastian. The fact that Ciel was driven that far into despair is sad enough; but just the idea that every generation after him will suffer heavily and fall right into his exact position [[FromBadToWorse is downright horrific.]]
** At some point of the movie, Shiori tells Sebastian something in the lines of she feels relief during her nightmares solely because she doesn't have to see his face during them, leading to Sebastian calling her a "rotten ass brat" for it behind her back. This was most likely PlayedForLaughs, but there is still something sad to it if it implies that Shiori would rather deal with nightmares than have to face the demon who will one day devour her soul/most likely manipulating her 24/7.
* The end of the second musical. Eric's willingness to do anything to save Alan in itself is pretty tear-inducing, but it gets even worse when Eric ends up not only failing, but also being the one who kills his friend, shortly before he is killed by Sebastian.
** Cue emotional music as Sebastian and Ciel comments on the snow-like souls being released from Eric's body, and states how "there is no meaning in life and death, however beautiful things... are simply beautiful." as Alan and Eric stands up and walks together to the back of the stage.
* Alois's character song: [[http://www.youtube.com/watch?v=HaJjOxDXxmg The Slightly Chipped Full Moon]].
** Though Ciel does not really have a character song, the lyrics and melody capture his character turning his back on the good and light for the dark, and inevitable tragic end that awaits him when he accomplishes his goal. [[https://www.youtube.com/watch?v=V4-tn_7CHvw]].
* In the last scene of the seiyuu event, [[http://www.youtube.com/watch?v=2bFHJxmvs7Q Kuroshitsuji Red Valentine]], we're treated to [[BittersweetEnding what would have occurred had the second season never happened]]. [[spoiler: Sebastian, with the contract ended, has eaten Ciel's soul, but he's not happy as one may think- he quite obviously misses his young master. The scene opens on Sebastian having made a cake for the now dead Ciel, and carries through him coming to grips with the fact that there's no manor for him to protect, no young master to serve, there's nothing left for him.]] This apparently takes place [[spoiler: only a day after the end of the contract, as Sebastian says, despite in the past having seen a hundred years as no more than the blink of an eye, a single day can seem like an incredibly long period of time as well.]] It ends with Sebastian's famous [[CatchPhrase "I'm merely a butler/I'm a devil of a butler"]] being twisted into "I'm merely... alone/I'm a lonely devil".
-->'''Sebastian''': Like falling snow... Everything disappears, before you can savor it.