Black Butler (manga)/Tear Jerker

Freckles. Freckles, Freckles, Freckles. Dear God. Freckles. After that particular piece of nastiness, Ciel's grasps at redemption were pretty sad to see. "Would you like an orange, sir?"
The whole end of the circus arc was this.
In chapter 44, watching Maylene and Finnian's breakdown after it seems to seriously and completely dawn on them that Sebastian is dead is utterly heartbreaking. Luckily, Sebastian is not really dead.
The final episode of anime season 2 which is either a Bittersweet Ending or an outright Downer Ending.
Madame Red's death at the chainsaw of Grell, and Ciel's reaction. "Red is... your favorite color". SOB.
Madame Red's funeral. The red dress and the rose petals... good God! *sniffle*
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 absolutely heartbreaking shot of Ciel's 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.
Chapter 61. When Sebastian gets 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.
In the anime, Ciel appears downright cruel at times, although in the manga, he is simply just icy and elitist. It's eventually revealed that he was a happy, loving, carefree child before his tenth birthday. Then his parents were murdered, the mansion set on fire, and he was kidnapped. He was locked in a cage with other children his age and eventually was to be a child sacrifice until he called upon a demon in his desperation to live.
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.
- I know! Seeing Ciel break down over Sebastian's body made me think "He really does have some kind of heart" because he's always been a jerk. Then we find out Sebastian dying was all and act by Ciel anyway, which totally crushed my hope.

The Musicals

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.
Go listen to Unmei from the musical. I'll wait.

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