HenchDevil

HenchDevil is the slash ship between The Devil and Henchman from the Cuphead fandom.

Canon
In the game, Henchman appears as one of the fat demons, who are enemies fought in the One Hell Of A Time boss level of Inkwell Hell. They only appear in the third phase of the fight, where they are brought into the stage as The Devil grabs their backs with his hands and drops them into the ring. The Devil stops summoning them after he gets damaged enough and starts crying.

In The Cuphead Show!, Henchman and the Devil are usually seen with each other, at least when the latter is in the Underworld and not trying to take Cuphead's soul.

In "Carn-Evil" (S1E1) Henchman is writing down the soul counter before the Devil starts singing, during which he smiles upon noticing his boss. During the song where the Devil starts dancing, he interruptedly tells him that the soul counter has surprisingly stopped. Later when Cuphead and Mugman escape the Carn-Evil, which is breaking down at this point, he catches up with the Devil and expresses his surprise as he has never seen him let someone escape before. The Devil tells him that he didn't escape and insists to get revenge on Cuphead by taking what he owes him: his soul. When Henchman corrects the Devil when he refers to Cuphead simply as "Cup" by adding the word "Head" immediately afterwards, the king of the Underworld hits him on the head with his trident.

In "Roll the Dice" (S1E5), Henchman is sent to retrieve King Dice after his failure to obtain Cuphead's soul. He excitedly asks for King Dice's autograph in the elevator down to Inkwell Hell, but is rejected. The Devil seems to appreciate Henchman, such as knowing that he is a big fan of King Dice's show and never misses an episode. After the Devil admonishes King Dice for disappointing him and letting Cuphead get away, he announces that King Dice is no longer his Number One and demotes him from hosting his show. Instead, he gives the position to Henchman. He is much clumsier dancer than King Dice, and falls into a band member's tuba as the episode ends.

In "Sweater Off Dead" (S1E8), Henchman is touring the Gluttony Department with the Devil, before the Devil holds a party in celebration of collecting souls. He then joins in on a conga line from the Devil after he tries to get rid of Stickler. After the Devil has to go out to collect Cuphead's soul, Henchman sarcastically compliments Stickler. According to Megan Ann Boyd, there was actually going to be a scene where the Devil would've asked Henchman to dance with him, in order to avoid Stickler.

Henchman cares for The Devil and wants to do everything to help him, such as trying to cheer him up with some cake and caring for his wounds, as shown in "Sweater Luck Next Time" (S1E9). Demonstrated in the same episode, The Devil trusts Henchman enough to admit to him that he failed to get Cuphead's soul. The Devil also seems to pay attention to Henchman's advice, notably concerning the Obliterator, which could allow him to force Cuphead to remove his invisible sweater.

In "Release the Demons!" (S2E8), seeing the Devil tearing the pages of a book entitled "Controlling Your Rage," still upset about not having retrieved Cuphead's soul yet, Henchman tries to lighten up his mood by complimenting him about his fur having almost grown back and attempts to calm him down with some tea, to no avail as the Devil blasts it with his pitchfork once he hears the word "cup." He is later seen helping the Devil send a squad of his finest demons. However, as he expresses his vengeance about Cuphead, he accidentally ends up destroying them, as well as his second finest demons. Over the course of this, Henchman demonstrates his cognizance of the Devil's incinerating outbursts, hiding behind a stalagmite and later pulling King Dice back too. Throughout most of the episode, Henchman corrects the Devil when he refers to Cuphead as "cup". Although it's clear that the Devil is very annoyed by this, he merely thanks Henchman for reminding him.

In "The Devil's Pitchfork" (S2E13), Henchman attempts to cheer the Devil up, who is upset over no longer being able to collect Cuphead's soul because he missed the deadline, by reading the headline of the newspaper. This doesn't work until he hears a review about him, and how that his touch is getting frantically weaker, thus angering him and using his pitchfork to roast the newspaper. Henchman then encourages the Devil to cause mischief around Inkwell Isles and thus finally cheers up the Devil, who thanks him (sincerely this time) and goes out to do so. Afterwards, the Devil blissfully tells Henchman about the trouble he caused. Later in the same episode, Henchman helps him look for his pitchfork and tells him to retrace his steps, which makes him realize that he left it lying against a tree. Shortly thereafter, they find Cuphead and Mugman are the ones who have Devil's pitchfork. The two demons are later seen descending with Mugman in the elevator, leaving Cuphead standing in the woods alone, devastated.

Despite the fact that he gave the invisible sweater to Stickler, who the Devil is incredibly fed up with, the king of the underworld does not seem to be angry with Henchman about it after he finds out and doesn't even bring it up.

In "The Devil's Revenge!" (S3E1), Henchman and the Devil make a friendly bet over whether the Devil will succeed or fail to break Mugman's spirit before the clock strikes twelve, where the Devil bets he will. Knowing how slimy the Devil is when it comes to betting, Henchman is quick to warn him not to cheat beforehand, cutting him to the quick. Over the course of the episode, while the Devil tries to win the bet without cheats, he eventually attempts to cheat after noticing that it's almost twelve. He lies to Henchman about having some dry cleaning for him to pick up. Though temporarily fooled, the Fat Demon is quick to realise his boss is lying and catches him in the act when he tries to turn the clock back. Although the Devil tries to excuse himself, Henchman is not convinced in the least and expresses his disappointment in the Devil for trying to cheat. The Devil, still trying to cover his tracks, calls Henchman rude, to which his assistant only responds that he ought to be ashamed of himself. Through this, it is shown that the Devil really can't fool Henchman. They briefly argue until they notice the cup brothers escaping. At the end of the episode, Henchman has won the bet.

In "Cupstaged" (S3E3), the Devil when he holds a performance for his workers. However, Henchman is the only demon to cheer for him as the other spectators are not that intrigued. Later, Henchman accompanies the Devil after learning that Sally Stageplay is hosting auditions for Inkwell Isle's most ambitious show to date: Cup Rogers vs. The Meteor: A New Space Opera. The Devil's motivation to audition is that while he may be feared, he wants to be adored and appreciated in the theatrical arts. Though Henchman claims that he adores him, the Devil insists that he wants to be appreciated by random strangers.

In "Roadkill" (S3E4), The Devil orders Henchman to bring more doughnuts after Stickler has made him drop his. Due to his indolence in retrieving all the souls he lost due to Cuphead and Mugman or collecting souls in general, the Devil, according to Stickler, has activated the Bubbles of Failure that entomb everything the Devil cherishes to encourage soul collection. If he doesn't collect a single soul within a business day, all assets will remain permanently seized. Henchman also appears trapped in one of those bubbles, subtly indicating that he is one of the things the Devil loves. Near the end of the episode, after The Devil returns to the Underworld, having brought back a soul (the Telephone's), he catches his assistant after the bubbles begin to break, leaving the Fat Demon flattered. He asks if he got more doughnuts, to which he replies that he couldn't as he was in the bubble.

The two demons are the focus characters in "A Very Devil Christmas" (S3E6). The special is focused on the Devil trying to enter Santa's nice list (with Henchman's assistance) and helping him deliver the toys in order to get a toy train. After the Devil learns about the "Nice List" and the "Naughty List", he returns to the Underworld during a round table discussion and learns that Henchman and the other Imps already knew about them. The Devil asks Henchman why he didn't tell him about the "Nice List", to which he replies that he didn't think it was his type of list as he is evil to the core. After a visit to the North Pole, where the Devil asks Santa Claus for the toy train he wants and later gets assistance to gain a place on the Nice List by turning into Santa, he and Henchman begin a journey to deliver the gifts for everyone on the Nice List, with their last destination being Cuphead and Mugman's house, which is when the Devil discovers that the gift Cuphead wants is the same toy train he wants. Though considering to keep it at first, the Devil eventually lets the little cup have it, who wishes him a Merry Christmas (without knowing that he isn't Santa). As it was something nice to do, the two demons are delighted to see that the Devil's name has been added to the Nice List. When they return to the North Pole, having successfully delivered the presents, the Devil soon turns back to normal. When he asks Santa about a toy train again, Santa tells him that his present is even better than that: the joy of being nice. Though Henchman is touched, the Devil becomes furious and quickly ushers Henchman to return to the Underworld. At the end of the episode, the Devil is upset about not getting the train he wanted, even after doing everything he was supposed to, only to be greeted with a surprise: a bigger train with an even better "choo-choo" sound than the one he originally wanted. Believing that it was Santa Claus that brought it to him, he blissfully jumps aboard and starts playing with it. It's then revealed that it was Henchman that built it for him. Smiling from behind his boss' throne, he wishes the Devil a Merry Christmas.

In "Down and Out" (S3E8) the Devil and Henchman come across King Dice again after they decide to go to the "new club" the latter heard about (mainly to avoid going through a ledger review with Stickler). There, they find Dice performing. During the break, the Devil tells Henchman to wait outside and confronts Dice, reminding him of the last time he was unable to capture Cuphead, revealing that, if he failed, he would destroy him. However, instead of being terrified, King Dice reassures him that it's all part of his plan to make up for it: with Cuphead believing to be his "manager", he's planning on getting him to sign a business contract, which gives ownership of his soul directly to the Devil. Hearing this, the demon decides to give his former Number One one last chance. King Dice presents the scroll to Cuphead as a contract that confirms the cup as his official manager, only to be turned down, with Cuphead claiming that "music's out and comedy's in", using Mugman's ventriloquism as an example. This infuriates the Devil, who proceeds to leave with Henchman back to the Underworld. Just before they get in the elevator, they notice Dice walking out of the barn and the Devil stops him. Near the end of the episode, however, a more positive interaction is seen between the two. While the Devil is very disappointed in King Dice, he admits that Dice "has something that's been sorely lacking from the organization for too long" and how it needs "his glitz, pizzazz, and razzle-dazzle." Though baffled at first, King Dice agrees and the two demons welcome him to the elevator with them.

In "Dance with Danger" (S3E10), the Devil and Henchman appear alongside each other when Chalice makes a deal with the Devil to be resurrected.

In "The Devil & Ms. Chalice" (S3E11), Henchman cheers for the Devil and Chalice after having performed a dance routine. The king of the Underworld and his assistant are later seen observing Chalice to ensure she holds her end of the favor to betray Cuphead and Mugman, and get them to sign soul contracts. After she rips the contract, the Devil becomes infuriated and, after a bit of pushing from Chalice claiming her dancing to be the best, suggests to sort things out with a dancing competition. If she wins, she gets her life and doesn't own the Devil anything. If the Devil wins, he obliterates Chalice. Eventually, the Devil wins. Just as he is about to obliterate Chalice with his pitchfork, Cuphead steps in and challenges the Devil to a "Rock, Paper, Scissors" competition. If the Devil wins again, he turns Chalice to ashes and claims Cuphead and Mugman's souls. Beforehand, he orders Henchman to hold his pitchfork and begins the challenge with Cuphead, which the latter wins multiple times, subsequently upsetting the Devil more. The Devil desperately demands a rematch but Henchman tells him it's time to go. Admitting to having been defeated, the Devil hangs his head in disappointment. As the two demons head to the elevator, Henchman comforts the Devil and manages to brighten him up a little bit by giving him his pitchfork, as it always cheers him up, and offering to draw him a bath, to which the Devil expresses gratitude.

Fanon
This pairing is somewhat popular, though not as popular as other ships with the Devil, such as DevilDice, likely due to Henchman being established as an actual character in the franchise years after the game was released. Some of the main reasons people ship these two is because there is a lot of chemistry between the two and of how their unique interactions stand out from most villain-sidekick duos as they are between two archetypes. Despite Henchman's clumsiness, the Devil is rarely aggressive and notably a lot less harsh towards him, compared to his other minions. Even when Henchman annoys him, the worst the Devil does is just give him a sarcastic, "Thank you, Henchman," even when alluding to things that will bring out the Devil's extreme anger. Though alarmed about the Devil's anger, Henchman is ultimately not afraid of him whatsoever and is likely the only person in the setting who can safely counter his boss' volatile behaviour and calm him down. He has a friendly and respectful approach towards his boss, which he reciprocates and genuinely values on some level. On a smaller side note, Henchman might technically be in about the same age range as the Devil, who could be about over 3000 years old, even though the Devil is generally paired up with grown adults regardless.

There's quite a bit of fanart involving the ship (though it's mostly posted on the characters' separate tags than the pairing's tag itself), in which they're often depicted either with the Devil leaning on Henchman's head, holding hands, or hugging (which is mostly initiated by the Devil). Other fanart references the scenes where they dance together (see above and Trivia) and where they take Mugman to the Underworld.

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Henchman x Devil tag on TikTok

Devil x Henchman tag on TikTok

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Trivia

 * Originally, Devil avoiding Stickler in "Sweater Off Dead" used to be a longer montage in which he asks Henchman to dance with him in order to eschew his auditor, as shown in a Twitter post by storyboard artist Megan Ann Boyd.
 * Head writer Deeki Deke once expressed agreement on Twitter about the Devil and Henchman being a healthy relationship and hinted that the next season will dive even deeper into their dynamic.
 * The pairing has seen a resurgence in popularity within the fandom as of the release of the second season.
 * According to the Devil's voice actor, Luke Millington-Drake, following a few questions from fans in an open Q&A segment on Twitter for his character:
 * The Devil is learning how to knit so he can also knit an impenetrable sweater to protect himself  from Stickler and to make Henchman a blanket.
 * Although the Devil claims that he wants no friends and only souls, he admits that Henchman is fun - sometimes.
 * The Devil considers Henchman to be the least insufferable in hell and says he occasionally makes him chuckle.
 * The Devil's favourite album is 12 songs of people screaming in pain, which was a gift from Henchman.

Variations

 * HenchDevilDice refers to the ship between the Devil, Henchman, and King Dice