Hazbin Hotel/Tear Jerker

Charlie dialing Lilith to ask for some help and motherly support. She has to convey her fears and worries in a single voicemail. And The Reveal in the season finale makes it so much worse.

Season One

The story of Lucifer and the apple; he fell in love with Lilith, who chose him over Adam, and wanted to spread knowledge. So he gave Eve the fruit -- didn't tempt her, gave it to her-- so that she and Adam would have free will. Instead, free will led to humanity making terrible choices, and Heaven cast both Lucifer and Lilith into hell for introducing evil into this new world. Lucifer was so horrified by this that he sank into a Heroic BSOD for millennia, unwilling to rule Hell.

Charlie attempts to help Angel get more time off, only for her to set Valentino's studio on fire. She offers to repair it, and rages when Valentino uses her mistake to torture Angel in front of her. Angel shouts at her to go, and she leaves while miserably slumped.
The song "Poison" as Angel hides how absolutely miserable he is to do Valentino's bidding as a porn star and sex slave. He pretends that he enjoys all the attention, but his voice breaks near the end.
Angel admitting to Husk that part of the reason he destroys his body with drugs and meaningless sex escapades is that he hopes that one day Valentino will find him too damaged to torment.

Lucifer's depression has been ongoing since the beginning of time, but Lilith vanishing made it even worse. He spends his time talking to rubber ducks and only snaps out of his funk when Charlie calls him. And Lucifer knows he is a mess, and fears that if Charlie tries negotiating with the angels, they'll break her too.

Charlie's Heroic BSOD where, just as it seems that the angels are arguing about the purges and they may make changes, Adam breaks her by revealing that Vaggie is a Fallen Angel like him. Also, she was once an exterminator who led the purges.
The reason why Charlie loses: Sera goes Because I Said So despite Emily pointing out that Angel Dust changed for the better and met Adam's criteria to improve himself. Adam rubs it in by saying the Hotel is the next target for the purges.
Emily is utterly betrayed when Adam opens his big mouth about the purges. She questions Sera for approving them and calls her out for permanently killing souls in Hell. Sera tries to placate Emily by saying that Hell was planning an uprising, giving her a motherly kiss on the forehead. It also comes with the warning that if you start asking questions, you will fall like Lucifer.
The fact that Lucifer was right: you can't reason with the angels. He warned Charlie, but she felt she had to try. Instead, Charlie painted a target on her friends' backs.

Vaggie is swimming in guilt that it's indirectly her fault Charlie lost. If she had told Charlie before about being a Fallen Angel, they might have still lost but Adam wouldn't have ambushed them.
Charlie starts the episode sobbing in bed, as Razzle and Dazzle tend to her. As Husk puts it bluntly, she made things worse for Hell by trying to reason with heaven. She even tells Alastor to fuck off, alerting Alastor that something is really wrong.
As Charlie tells Alastor and later Rosie, the issue isn't that Vaggie used to be an Angel. She understands that Vaggie is not the Exterminator she used to be. It's that Vaggie lied to her by omission, when Charlie has been completely honest with her about everything, including her most embarrassing secrets.

When Adam starts attacking the hotel residents, Charlie briefly worries that Alastor is dead. You can tell she truly cares about him and is relieved when he reappears at the end.
Sir Pentious's Heroic Sacrifice which at first seems senseless. He kisses Cherri Bomb and says he loves her before taking most of the Egg Boiz up in his airship, preparing to fire a Death Ray on Adam. Sir Pentious knows that it was a longshot, and is proven right when Adam sees the attack and incinerates them, airship and all. He still tried to at least give his friends a chance of surviving.
- The Hotel residents' reactions. Charlie screams, and Angel Dust can only say while crying, "Fuck, you did good, buddy."
- Happy tears ensue when we find out that Sir Pentious's self-sacrifice leads to him entering heaven.
Adam's attempt to use the same attack on Lucifer slices the hotel in half, destroying it down to the foundation. When the dust settles, Charlie manages all the damage.

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