Cup Brothers

Cup Brothers is the family ship between Cuphead and Mugman from the Cuphead fandom.

Canon
Cuphead and Mugman are two young brothers living on Inkwell Isle, living under the care of wise Elder Kettle. They had little reason to complain, every day was grand, but one day, they dared to go outside the borders of their home.

Cuphead
In the original game, Cuphead took Mugman with him to Devil's Casino run by the shady King Dice. They soon found out that they had incredible luck and seemingly couldn't lose a single game. But then they were challenged by the Devil himself, the casino's owner into raising the stakes: The Devil offered all of his money in exchange for their souls. Cuphead nodded and grabbed the die, throwing the soul of his and his brother away. Mugman realized the danger, but it was too late to stop Cuphead. But the Devil and King Dice had already expected them to lose and the Devil demanded their souls. But they both fell to their knees, pleading for their very lives. Mugman offered another way to repay the Devil and Cuphead agreed. The Devil accepted the offer and handed the brothers a list of runaway debtors, collecting their souls instead shall set them free. The Devil then literally kicked them out and giving them a deadline: Midnight tomorrow. Cuphead, terrified of his life for the first time, suggests to his brother to ask Elder Kettle for help.

Elder Kettle couldn't help them beyond telling them to heed the Devil's request, giving them a potion to access magical abilities to defend themselves. He then trained them by having them enter a piece of paper on his writing desk, drawing an obstacle course for them to serve as a tutorial. So Cuphead and Mugman are given the option to work together to defeat the debtors. With both in a battle, it unlocks the ability to parry the other back to life, technically allowing battles to go on indefinitely should the players be skilled enough to revive their partner in time.

Proceeding to Inkwell Isle II, Elder Kettle catches up to them, telling them how impressed he is by them growing stronger and that he is sure that they can defeat the Devil if they keep going like this. Even King Dice agrees when he allows for them to pass through, telling the Devil all about their feats when they finish Isle II. The Devil admits that he saw something "special" in them, but blows off King Dice's warnings, telling him he'll be prepared for them.

King Dice was still betting against them, as impressed as he is, he wasn't going to take losing a bet, so he challenges them to a fight once they are done with Inkwell Isle III. Despite that, they manage to defeat him as well and wander on to challenge the Devil next. But when the Devil sits on his throne, he is as calm as a lamb and simply offers to have them join him should they actually agree to handing over his soul contracts. They can actually agree to this, causing Cuphead and Mugman to lose their souls for good, becoming ammoral hellspawns in the process.

But what they are ought to do is refuse to hand them over, to which the Devil reveals that every other debtor tried the same, so he challenges them to a fight. The Devil surrenders at the end of it and the brothers are kind enough to leave him be. However, they still burn his contracts, freeing the debtors of their lot in one fell swoop. They can't wait to tell everyone that they're now free, with Cuphead spreading the good news and Mugman assuring everyone that the Devil won't bother them any longer. They made Elder Kettle very proud and all the debtors forgot their gripes with them and cheered for them together. They made a promise to never wander into trouble again, but they were fully aware that they might not heed that promise until "next time".

Fanon
Given that they are the two main characters, logically a large amount of fanwork is focused on the brothers. Though they're generally portrayed as getting along well, it's not uncommon for fans to make Cuphead a bit of a bully towards his brother, given that he was the one who roped him into the mess.

People often compare them to the Mario Brothers, with Cuphead being like Mario in that he's more outwardly fearless, while Mugman is more timid like Luigi. Some even draw Mugman to closer resemble Luigi, especially regarding him being called "Mugman" as slightly odd, since he and Cuphead have the exact same headshape.

Some also compare them to the Disney Brothers, given that their color schemes match. Though unlike Oswald, Mugman is often considered to be the younger brother.

Fandom

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