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 Season 3 premiere, 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.

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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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