That's a helluva way to finish the season.
With Cuphead and Mugman down, Miss Chalice, now intending to make up for what she had done to her two best friends, decides to square off with the Devil to get them back. However, Old Scratch is full of surprises, and Miss Chalice might have to do more than pull out all the stops to best him.
Tropes
- Alas, Poor Yorick: As a preview of her punishment, The Devil turns Miss Chalice to dust and bone and takes her skull, dryly saying "Alas Poor Chalice, I knew her well," before apathetically dropping her head back on her remains and restoring her body and soul.
- Best Out of Infinity: When the Devil loses to a game of Rock–Paper–Scissors, he repeatedly makes a "best two out of three", which gets higher with every loss he gets.
- The Cameo: Among the Inkwell Isles residents seen during the Dance-Off are the Root Pack, Bowlboy, Sammy Sandwich, The Elephant Couple, Sherman and Doris, the Ice Cream Man, Porkrind, Jerry, Ribby, Croaks, The Saxophone, Cherry, The Screwdriver and Sally Stageplay. And Telephone.
- Dance-Off: Unable to bring herself to betray her friends, Miss Chalice challenges the Devil to a dance competition to free her soul and prove who's the better dancer between the two.
- Didn't Think This Through: Cuphead challenges the Devil to Rock-Paper-Scissors because according to him, he has an 85% chance of winning. Mugman and Chalice then remind him that at Rock-Paper-Scissors, both sides have an equal chance at winning, which Cuphead calls something he could've known yesterday. But luckily, he ends up winning over the Devil in each round.
- Heart Beats out of Chest: As the Dance-Off is intensifying, Mugman's heart is pounding out of his chest in anticipation before Cuphead pushes it back in.
- Moving the Goalposts: Every time Cuphead wins the match round of his and the Devil's Rock-Paper-Scissors, the latter raises the "best of" number higher and higher until Mugman stops it.
- Near-Villain Victory: The Devil wins his and Ms. Chalice's dance-off and is about to take her soul, until Cuphead intervenes and challenges the Devil to Rock–Paper–Scissors, and ends up winning every single one of their rounds.
- Nice Job Breaking It, Hero: The sack of marbles Cuphead gives Miss Chalice as a gift spills open during her Dance-Off with the Devil, causing her to slip and lose the contest.
- Nobody Calls Me "Chicken"!: At first, the Devil finds Cuphead's duel between them to be Rock-Paper-Scissors to be stupid, because there's no strategy or skill involved. Cuphead then calls him a coward in front of the entire crowd, and only after that does the Devil agree to the deal.
- Rapid Aging: To remind her what would have happened if he didn't revive her, and to keep her in check, the Devil tortures Chalice by reducing her to a sack of bones before reviving her.Henchman: Aw jeez. This seems unnecessarily graphic.
- Record Scratch: Miss Chalice and the Devil are about to dance again when Stickler stops the record player, causing a loud scratch.
- Rock–Paper–Scissors: Cuphead bets to the Devil his soul alongside Chalice's freedom and Mugman's soul by playing this game against him and wins every single round.
- Sequel Hook: The episode ends with Mugman and Chalice attempting to stop Cuphead from entering the Devil's Casino leading to the events of the video game.
- Shout-Out:
- The title is likely a reference to The Devil and Daniel Webster.
- When the Devil tortures Chalice with a horrible death, the dark ghastly spirit that shoots out of his pitchfork to overwhelm her most likely resembles the spirits that are released from the Ark of the Covenant to destroy the Nazis in Raiders of the Lost Ark. Also, Chalice's horrified expression as her body becomes brittle and decomposes from her bones, her face and hands and whole self melting away and crumbling into dust while she is mobile, terrified and in agony even when she should have died, is similar to Walter Donovan's fate after drinking from the wrong grail in Indiana Jones and the Last Crusade.
- After Miss Chalice loses the dance competition, Cuphead challenges the Devil for her freedom. One of the options the Devil suggests is "fiddle playing", a reference to the Charlie Daniels Band song "The Devil Went Down to Georgia".
- The Devil keeps demanding more rematches to Cuphead's growing win streak in a similar fashion to Death.
- Sore Loser: The Devil doesn't take it well losing to Cuphead at rock-paper-scissors and constantly asks for more chances when he keeps losing until Mugman has enough and calls him out.
- Stealth Prequel: The ending of the episode ends with Cuphead eagerly running to the newly opened Devil's Casino, implying that the whole show is actually a loose prequel to the video game.
- Villain Ball: There really was no reason for the Devil to accept Cuphead's challenge after he'd already beaten Ms. Chalice, but because he's so obsessed with getting Cuphead's soul as well, he forsakes a win he's already gotten in favor of a win he might not (and does not) get.
