Cuphead just wanted his brother back.
That was all he'd ever wanted, really - money would have been nice, so would power, but he never realized exactly what his most valued possession truly was until it was gone.
Mugman. It was always Mugman. They'd been together longer than either of them could remember - together in their mother's womb, together in their first crib, together in the orphanage later on, and together in Elder Kettle's cottage.
Sure, they had fights - all siblings did. But they always reconciled in the end. Mugman was always there for Cuphead, and vice versa.
Cuphead wished he'd just given back the Devil's pitchfork, then they wouldn't be in this mess - but he didn't, and their situation was as real as the Devil himself.
Cuphead had gone to Quadratus for help after his brother was taken. The wise old deity in the pool had been extremely unhelpful at first, but had finally given him the tool needed to create his only means of transportation to the underworld. Cuphead created his elevator and packed up the tandem bike Mugman had made inside of it, and then he was there in hell, standing in front of the Devil after a failed escape attempt.
The Devil, unwilling to hand over his hostage for any small price, offered Cuphead a deal - a heartbreaking one.
Mugman could leave, but Cuphead would be staying right here in hell.
What could he do? Cuphead couldn't just leave his brother here in hell - even if Mugman had lasted this long, he'd surely start to feel the heat eventually. The Devil wasn't likely to be kind to him in the least if Cuphead rejected the deal.
But at the same time... if Cuphead accepted the deal, what unspeakable horrors would await him there? It was hell. It wasn't known for being a vacation spot - especially not for the Devil's most loathed person. Even if he could escape, he'd surely never be the same again...
Was it worth it?
Cuphead took a deep breath.
"Yes."
The Devil smiled.
"I knew you would make the right choice," said evil incarnate, holding out his hand. "Now, if you please, give me my pitchfork - and kneel for me, would you?"
Cuphead handed the stolen pitchfork to its owner and lowered his head, his face burning with anger, hatred, and humiliation as he bowed to the Devil.
But nobody left hell that night.
The Devil was happy to have his pitchfork back - he twirled around and kissed it, humming a little tune happily - and then turned back to the brothers, who were staring at each other, Cuphead smiling sadly and Mugman on the verge of shocked tears.
The Devil started to laugh. The brothers glanced at him, then edged closer together as his laughter grew louder.
"You... utter... fools!" the Devil laughed, wiping a tear of laughter off his face.
"You didn't really think that I was going to let you both go free, did you?"
Cuphead suddenly realized just how badly he had messed up, as the Devil grew huge above them and reached down to grab him and a frozen Mugman.
As the two of them closed their eyes they grabbed onto each other, both determined to never let go.
Cuphead and Mugman had been imprisoned for so long, they could barely remember the feeling of a cool breeze, the taste of Elder Kettle's pancakes, or the sight of the blue sky overhead.
Maybe it had been three days, maybe it had been three years, but the time made no difference to the sweltering heat of the flames that often licked the bars of their cell and the painful chips and cracks they had sustained from the guards who would occasionally rattle their cage, or pull them out and shove them around.
The only thing keeping Cuphead sane was Mugman, and vice versa. Every day, Mugman would remind Cuphead to recite his name, age, birthday, and favorite things in the morning. Every once in a while, however, Mugman would break down crying and rattle the bars, screaming for the guards to let him out - and then, Cuphead would hold him as he sobbed his heart out. Gone were the days of petty arguments and hitting each other - so was everything about their childhoods.
Now, demons always scuttled through the area. Sometimes they would laugh at the boys and taunt them. But one night, two especially large demons came right to the cell.
The demons opened the doors, and one ducked inside as the brothers backed away fearfully, holding onto each other tightly.
"Cuphead?" Mugman whispered, eyes wide. "Why are they here?"
"How should I know?" Cuphead hissed, trying to seem brave despite how hard his heart was pounding.
The large demon looked over them. He grunted and grabbed them both by the handles, yanking them away from each other.
"Hey!" Cuphead protested, kicking and punching air and trying to turn around. "The hell is this?"
The demon carried them both out and threw Mugman uncarefully to the other demon, who caught him. The blue-strawed mug was too frightened to move, let alone resist, as the demon twisted his hands behind his back and tied them. Cuphead kicked and struggled, but a few minutes later, both boys were bound and being marched through hell.
"E-excuse me, sir - w-where are you taking us, exactly?" Mugman stuttered.
Neither demon answered.
They marched the boys through hell at a quick pace, and all arrived at a large double door.
The doors opened into a huge stadium. It was very well-lit for hell - there were many large lanterns hanging among the seats and above the arena. However, despite the relative brightness of the stadium, an aura of dread hung in the air, infecting the brothers and making both feel queasy. Even more disconcertingly, the seats were nearly all empty but for a few in a VIP box. Cuphead, squinting, managed to just barely make out five figures - a gray and horned one, which was clearly the Devil, but several unfamiliar silhouettes as well.
Cuphead didn't have much time to ponder, as before he knew it, a club was being shoved into his hand and he was being dragged out into the middle of the arena.
"Wh-" Cuphead looked at Mugman beside him, who was rubbing his arm where the demon guard had held him. "Mugsy, what the hell's going on?" Cuphead hissed.
"Well I don't have a clue!" retorted a wide-eyed Mugman, tightly gripping the club he'd been given.
A door on the other side of the arena opened, and a large, gray cloud swirled out. The cup brothers backed away from it as it assembled itself into... a giant cigar?
Both brothers blinked a few times. Yes, it was a cigar - a huge cigar with large eyes and a grimly smiling mouth.
An upbeat jazz instrumental began to play from somewhere, registering only as white noise in Cuphead's rapidly-overloading brain.
Cuphead looked around wildly, from the giant anthropomorphic cigar, to the Devil in the stands, to the ceiling high, as a disembodied voice blared from an unknown place.
"A brawl is surely brewing!"
Suddenly the realization hit him, and by the looks of him, Mugman as well.
This was a fighting arena.
This was why they had clubs.
This was their enemy.
They looked at each other in horror as the cigar took a deep breath in, ready to begin his attack.
"Now go!"

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