Cuphead Watch Party: Dissecting Season Three

Okay, I was not expecting to get all of The Cuphead Show in one year. That was three seasons? With the DLC slipped in-between as a pleasant surprise to interested fans? What a rush! I may need to take a step back to assess and rewatch. In fact, I should, with the realization that the show is over.

The creators went off-chain in this season in the episodes that do not focus on the main plot of the Devil seeking Cuphead's soul. They knew it was the last one, so they decided to go all out in the different plots and absurdity. The Devil alternates between antagonizing the cups and preying on them, to treating Cuphead as a casual frenemy. Their dynamic in some episodes reminded me of the relationship that Sonic and Eggman had in the Sonic Boom series. Sonic and Eggman are enemies, but there are some episodes where they can tone it down to annoyed neighbors in a sitcom-style relationship. Yes the Devil reminds us that he is a threat, especially towards the end of the season. He can also get petty when he and Cuphead audition for the same part in a theater.

Plotwise, the Devil's quest to secure the cups' soul gets resolved. Fortunately, the viewers aren't given a choice about how that will go so there is no bad ending. Instead, we get a pretty happy one, with a promise of more adventures.

We also get a resolution to the mystery of Chalice, and why she is on the lam for most of her screentime. Turns out she's not just a con artist that can rack up a lot of wrath for her charm; she has her reasons for wanting to keep moving. Yet Cuphead and Mugman legitimately won her over by treating her like a person and showing interest in her life, and that causes her to make a drastically different decision compared to when she bailed on them in the season one finale. Who knew a love letter to vintage cartoons would have character development?

The Devil's flaw

The Devil has lost his edge in season two, and season three is about his comeback. No one fears him anymore, and Stickler notes that he has gotten lackadaisical about his soul collecting. He spends a portion of season three building up his fearsome reputation while plotting revenge on Cuphead. Then the rest of season three tears those notions down.

We got a few episodes that centered in on the Devil. He is the funniest character in the show, owing to his voice actor hamming it up and it was great to see him front and center. I was laughing at the table reading of the season two finale this summer.  Season three gives him more to do, from auditioning for a local play or having fun on Christmas. We get to see more sides of him as a result.

As of the season three premiere, the Devil no longer has a claim on either Mugman or Cuphead's souls. Mugman never gambled his away, and Henchman expressly said that the Devil kidnapped the Mug, which is apparently against the rules. Whatever the rules are, the Devil may ignore them but he will pay for it. The Devil, however, vows revenge. He wants both of their souls, though he will settle for Cuphead.

The problem is that the Devil doesn't know when to quit, much like Cuphead. He could just know when to cut his losses or find another solution, like when he has to forfeit ownership of Cuphead's soul. Instead, the Devil persists to the point where folding would at least let him walk away and lick his wounds. Henchman literally has to pull him away in the series finale when Cuphead beats him multiple times. to say that a hot bath with bubbles is a better way to ensure the night is not a waste.

You can see this stubbornness in the second Christmas episode. The Devil starts off by freezing a bunch of ice-skaters, doing a few spins around their frozen bodies, and singing about how much he loves to create mischief. Rinse and repeat with more pranks and ruining people's lives as they go about their Christmas shopping. We get some parodies of the famous scenes from other Christmas specials, including from Charlie Brown, the Santa Clause first movie, and the Grinch. There's a lot to work with even before the real story starts, as we get reminders that the Devil may have become goofier, but he is still a clear and present threat to the mortal world.

Then the Devil learns about the nice list, and the naughty list, after seeing a beloved train in a windowsill. Santa updates them both to reflect who has been good and who hasn't been this year. Learning that he's probably not on the nice list, the Devil goes to the North Pole to ask the big red man to put him on it. Santa, a carbon copy of the 1930s Disney incarnation from two Silly Symphonies shorts, checks the lists and points out that the Devil is the incarnation of evil, ergo the naughty list. He says that the Devil could try to be a good person by the stroke of midnight, but the Devil shoots himself in the foot by burning a homeless toon alive while finding a good deed. Seeing that the Devil wants a second chance and will do anything for that train, Santa does a ritual that turns the Devil into the man in the red suit, and the Devil can only change back to his bony self while ending up on the nice list if he delivers all the presents on his list by midnight. Otherwise, he will be Santa for eternity. The thought horrifies Devil, and he works hard to be nice while eating cookies and delivering presents.

All this work was unnecessary. As Henchman points out, the Devil could create his own model train, with all the bells and whistles that he desires. The Devil says he wants to be given a train, for validation that he can be on the nice list. He ignores the simple solution like a gift exchange, but Henchman just does that. When Santa reveals that the Devil only earned a spot on the nice list but didn't get a train, the Devil throws a tantrum. Henchman is implied to stay up all night making a model train by hand, and ensuring that it will work with an even nicer sound. The set is also larger than the one in the display window.

The Devil misses the point that gifts are given out of love. Santa gifts children who are good out of the kindness of his heart, not just to reward good behavior but also to encourage it. Not even Saint Nicholas can love the Devil enough to gift him a present, and makes him work hard to ensure that he's earned it. Kudos to Santa for standing his ground and making a standard Christmas plot the worst possible punishment for the Devil. I was worried that him disappearing was going to be the "ruining Christmas" stakes but no, being jolly and red with the "ho ho ho" horrifies the Devil more than anything else that can be tossed at him. Instead of the Devil becoming a Grinch, Santa decides to end him. I tip my hat to Santa for trying to educate the Devil with such creativity.

The lesson doesn't stick, sadly, because for the Devil, the thought of being good for nothing terrifies him. He knows that he is a shameless trickster. The train only matters, because it is not available to him.  While I get the feeling, we know this guy is not nice.

Henchman, in contrast, understands the point. He squees when meeting Santa and volunteers as a substitute reindeer. When he becomes the number two, he helps give the Devil a pep talk after the latter learns that Cuphead is on the nice list, against all odds, and the Devil isn't. The joy of Christmas is not in getting what you hope as a reward for being good, but that you can show how much you care about someone else. That love doesn't need to be romantic or familial; it just needs to bring joy. Henchman acts on the platonic love that he has for his boss and puts in the work to ensure that the Devil gets some compensation for the rough night that he had. Yes it was the devil's fault. Henchman still loves the Devil regardless.

Chalice is allowed to be a kid

We learn that Chalice, unlike in the game, is Cuphead and Mugman's age. She was an orphan who busted out of a stern laundromat sweatshop where all the wards had to fold shirts while ironing them. One problem was that she had no money, which she solved by dancing for coins. If Chalice had stopped there, things probably would have been fine. But she had to use her charm to cut lines and receive nice stuff. She just made the mistake of running into the road to finish a number, where a car hit her.

I'm not sure how I feel about the divergence in backstory. Chalice, in the game, being a hero who gave her life for the Boiling Isles felt grandiose and epic. She put her money where her mouth was about being formidable, in the face of winning numerous coins. Playing as her does look like fun in the DLC, as does the eventual reveal about what the Wondertart needs to work properly.

With that said, Chalice gets some character development after hanging out with the boys. She bailed on them in the first season finale to save herself from the cops. Here, the Devil coerces her to get their souls, by making them sign a contract. Yet when push comes to shove, Chalice can't do it. She warns the brothers that the Devil owns her, and then challenges the Devil to a dance-off where her soul and body are at stake.

The dance-off is the first time we see the Devil participate fully in a challenge, with no bells and whistles or cheating. Before, it would feel like he'd use his magic to gain an unfair advantage or hurt the competition for spite. We even see that in the pilot where he can't accept Cuphead beating Soul Ball and went up to directly sabotage him. That's how seriously the Devil takes his dancing. He does win legitimately, owing to Chalice suffering some bad luck thanks to a gift that Cuphead gave her. Cuphead has to step in and save Chalice. By some sheer dumb luck and not overthinking, he actually does it.

Chalice felt she didn't need anyone because she had to look out for herself from a young age. The matrons at the orphanage forcibly stopped her feet, even swaddling her when she kept insisting on dancing. No one on the streets cared about her unless she entertained them. The Cups were the first two who asked about her and said that they wanted to hang out with her. Over the next two seasons, as Chalice loosens up, she finally relaxes around the brothers and enjoys herself.

I don't think the end of the show is the beginning of the game

Season three ends with Cuphead saving Chalice from the Devil with some quick rock-paper-scissors, and Mugman stopping Cuphead from persisting with the game long after the Devil had lost. A month later, Chalice is glad that it's all over while walking with the boys, before they spot a sign for a new casino. The Devil is running it. Just as Mugman scoffs that no one would fall for that, they realize Cuphead is sprinting towards the casino. Not willing to lose their souls again, Mugman and Chalice run to catch their brother, since Chalice is now obviously one of the family. Cue the ending credits. It certainly is quite a difference.

Mind that the game starts with Cuphead gambling away his and Mugman's souls at the beginning. There is a difference in the timeline: in the picture book opening in the videogame, Cuphead and Mugman don't know who King Dice is as he watches them gamble. In the show, they're both big fans of him and a season three episode has Cuphead selflessly help King Dice make a comeback after the Devil unceremoniously fired him. They're also not scared of the Devil when he appears, while even Cuphead has the sense to show some fear of Old Scratch.

The brothers also go to Elder Kettle for help in the game, which leads to the power-ups. He helps them, while showing disappointment about the foolishness of their actions. Elder Kettle in the show mistook the Devil for a cat, and the boys haven't filled him in on the gory details. It's likely that if Cuphead and Mugman had told him in the show, they would have avoided most of the Devil's nonsense.

Most importantly? Chalice isn't there with her dancing feet. Chalice in the game is somewhere trapped in a mausoleum until the brothers free her in optional boss fights. She also isn't alive and her backstory is drastically different compared to the implications in the game. We aren't getting the game's beginning, but the hope that Mugman and Chalice can stop Cuphead from doing something very stupid.

Closing thoughts on season three

2022 was the year of Cuphead. From the DLC to the new show, we were pretty lucky to get this much adventure and trouble in one go. The creators knew that we wanted some simple slapstick paired with love letters to vintage animation and a rather threatening villain. People were playing because they loved the art and music, and savored all of those victories. I know I did.

The Cuphead Show knew that adapting the game's plot wholesale would not maximize the entertainment potential. Having the Devil as a regular nemesis rather than a threatening Big Bad is side-splitting, especially when we meet the other denizens of hell. Stickler gets to show off some dry wit with a larger speaking role in season three.

I do wish that the seasons had been spaced out a little more. Part of it is the sadness that The Cuphead Show is done, and we won't get more of it unless Netflix changes their minds and orders a few more seasons. That finale tied up many of the knots, while providing a lot of laughs along the way.