"Alas poor Chalice, I knew her well."
- The whole situation with Cuphead’s soul debt from Mugman’s side during seasons one and two.
- His brother’s recklessness has gotten him in trouble with the actual Devil, who is now hunting after Cuphead’s soul. Sure, the brothers have managed to evade the Devil from collecting, but they haven’t yet found a permanent solution to this problem (prior to the reveal in season 2’s finale). The fact that Cuphead is so dismissive of the issue of his life being at stake and Mugman having to save him from several close calls as a result can’t be easy on him.
- There’s also the fact that Cuphead only lost his winning streak at the Soul Ball game due to Mugman accidentally making him miss when trying to warn him of the Devil’s arrival. One has to wonder if Mugman carries any guilt himself towards the situation for his (accidental) part in his brother’s soul debt.
- From Cuphead's perspective as well. Unlike in the game, he didn't know that he was betting his soul. All he wanted was to play a carnival game and now he has a soul debt on his head, which, despite insisting otherwise, he's clearly very worried about.
- Cuphead’s nightmare in “Sweater Off Dead” showcases in no uncertain detail that for all of Cuphead’s bravado, deep down, he’s a still a scared kid with a debt to pay to the Devil who will stop at nothing to collect. Moreover, it’s not just himself he’s worried about. He’s terrified at the prospect of his brother and Elder Kettle getting caught in the crossfire of his mess with the soul debt. According to Mugman, Cuphead’s been having these nightmares for a while. How many nights has Cuphead woken up screaming from his nightmares and how many times has Mugman listened to his brother still insist he’s fine when he clearly isn’t before finally putting his foot down to do something more proactive about the situation?
- The misunderstanding in “Dirt Nap” from Elder Kettle’s perspective. Imagine overhearing that the two boys you've raised with love and have always cared for think that you're old and disgusting, and want to kill you and bury you in the backyard to "put you out of your misery." His tearful confession to them of this belief near the end of the episode is heartbreaking. Even with the Poor Communication Kills aspect some of the scenes can be really sad. Especially when Elder Kettle looks at himself in a pot and says, "Maybe I AM disgusting..."
- Cuphead and Mugman getting thrown in jail at the end of the first season finale, "In Charm's Way". Viewers can't imagine the worries from Elder Kettle when he hears about this...
- Ms. Chalice bailing on the brothers at the cookie factory when the cops show up. At first she struggles to get the brothers awake so they can get out too, but to no avail. She confesses that she likes them but not enough to tango with the police. When she turns into a ghost, she has a look of regret on her face before she flies away. If you look closely at Ms. Chalice as she tries to get the brothers up, specifically where you can see her shaking in fear before confessing, she looks just about close to tears.
- The ending of "The Devil's Pitchfork".
- Despite Cuphead seemingly having the upper hand against The Devil by having his pitchfork and no longer owing him his soul, The Devil proves just how conniving he is by taking Mugman in retaliation. In the end, all Cuphead can do is look on, horrified, as his beloved brother is taken away and dragged to the underworld.
Cuphead: (in shock) …Mugman?- It gets worse when you remember that his nightmare from "Sweater Off Dead" involves Mugman being taken away from him—this is his worst nightmare, come to life.
- Prior to this twist, the episode did a good job almost making you pity the Devil and how low his reputation had sunk. He was mocked in the paper for losing all his Villain Cred because of Cuphead, and in his attempts to show he still has it, loses his pitchfork and is humiliated relentlessly with it by his enemy. After he accidentally blabs that he can't even take Cuphead's soul anymore, and thus is powerless to stop him anyway, he breaks down sobbing, at which point Cuphead seemingly shows sympathy...only to Yank the Dog's Chain and zap him again, laughing at his misery. No wonder the guy snapped.
- "The Devil's Revenge" picks up right where season 2 left off, with Cuphead being absolutely devastated, saying Mugman's name over and over again all the way home processing what just happened.
- When Elder Kettle sees Cuphead's despondence, he tries to comfort him, saying, "It's not like you lost Mugman." That's all it takes for his son to start blubbering inconsolably. Tru Valentino's acting just hammers it home here.Cuphead: (tearfully) Don't worry, Mugsy... I'll find some way to bring you home!
- At first, Cuphead can't even get himself to say what happened despite several attempts, and ends up half-heartedly lying and saying what he lost was his pocket knife.
- When Elder Kettle sees Cuphead's despondence, he tries to comfort him, saying, "It's not like you lost Mugman." That's all it takes for his son to start blubbering inconsolably. Tru Valentino's acting just hammers it home here.
- You can't help but feel sorry for the Devil at the end of "A Devil Christmas" when he trudges back to his throne miserably after spending a long and painful night of serving the role as Santa only for the latter to change his end of their deal to the joy of being nice instead of a toy train behind his back. (And the Devil did have the right to be angry at him for doing so). It does turn to heartwarming however when Henchman goes out of his way to build the Devil a toy train himself.
- All of Miss Chalice's backstory. To wit:
- She was raised in an Orphanage of Fear whose owners never let her have any fun and any attempt to have fun was met with harsher and harsher punishments.
- She only gets out by running away, which naturally leaves her living on the streets.
- After she manages to turn things around via mastering her charming tricks enough to become a Satisfied Street Rat, she gets hit by a trolley and outright dies. And this is a child.
- This culminates in a scene where Chalice is getting ready for her Dance-Off with the Devil and Mugman attempts to talk her out of it. Chalice's response? She doesn't have anything to lose. Ouch.
