A/N: Howdy, ya'll! Since the review policy is strict, I'm gonna respond to all your comments here!

snake screamer - Hmm...yeah I can see Stickler being an accountant (he technically already is one since he keeps track of how many souls are in the vault). Although, seeing as it's the Devil we're talking about, I highly doubt he pays taxes. It was Jesus who said to "give Cesar's things to Cesar" after all; naturally the Devil will do the opposite.

boygenius2020 - Thanks, I have a feeling it will be! Idk, I'm gonna let the readers be the judge of that lol.

KG - Nice to see you again! This is my third CH fanfic since I deleted a couple of 'em for maintenance reasons. They were out of date and needed desperate editing. But...it's possible I'll repost 'em again someday. Time will tell.

Also, I've heard of the possibility of them renewing for season 4, but it's unknown due to Netflix only ordering 36 episodes for the series, and they're furloughing TONS of animators rn. Until I hear otherwise, I wouldn't be surprised if they cancelled it. BUT...I agree, it would be awesome!

Guest - ...I wasn't really referencing the Devil with "if you want something done right, do it yourself", I've just heard every other villain say it in cartoons and movies.

Also...I did listen to the extended version...and I'm amazed. I love the idea of a reprise...in fact, I may take you up on it =)

With all your questions answered, here's the next chapter! Enjoy!

It has been one month since the fateful incident in Inkwell City. It was the greatest show the island ever witnessed – the battle of dance between the Devil and the charming Ms. Chalice and then the epic battle of rock-paper-scissors between said Devil and Cuphead. It was the most featured topic in the local Inkwell newspaper for several weeks.

Until this day.

Cuphead, Mugman, and Chalice strolled down the plains of Inkwell, each with a cone of two dips of ice cream in hand, enjoying the beautiful sunset.

"What a great day!" Cuphead chirped. "Hard to believe it's been a month since we've seen the Devil!"

Mugman closed his eyes with a smirk of satisfaction.

"Good riddens, I say!"

"And how!" Chalice added. "I am DONE dealing with the Devil."

"Same here!" Cuphead agreed.

That is, until he spotted a peculiar sign.

"Say, what's that?"

The trio looked up at the sign, which was filled with spectacular lights that blinked on and off, and had an arrow pointing forwards. It read:

GRAND OPENING: THE DEVIL'S CASINO

The trio were surprised at first, until Mugman scoffed at the disgusting sight.

"No way we're getting near that place."

"Yep. I think we all learned our lesson." Chalice concurred. "Right, Cuphead?"

No response from Cuphead, instead a cloud in his form took his place, the ice cream falling to the ground. Mugman and Chalice looked at each other with annoyance; they knew what this meant.

"Oh no…"

Cuphead rocketed toward the new casino, excitement clouding his better judgment. Did he realize that it's owned by the literal DEVIL of all people? Did he care? Eh, who knows; even Cuphead himself didn't really know for sure. What he did know was that a ton of fun was right in front of him.

The careless teacup barely heard Mugman and Chalice screaming his name from behind him. He was too consumed by his own excitement to really stop and listen.

"CUPHEAD!"

Right when Cuphead approached the casino, the doors opened, seemingly on their own. The obvious creep factor didn't deter him at all as he ran straight into the mysterious building.

And what he saw…was amazing.

The casino was filled with a large crowd, scattered all over the room. Cuphead wasn't thrilled with the suffocating smell of cigarette smoke, but he was filled with amazement at the bright lights, loud sounds of jazz music, and games he'd never seen before; there were slot machines, games of poker and blackjack, and roulette.

Cuphead looked to his left and…what was that? A group of skeletons gathering on a table, throwing dice at it.

"HA! I rolled a five!" One skeleton shouted. "I win!"

"Aw come on, Mac!" Another skeleton groaned. "You won the last roll!"

"Heh, you snooze, you lose."

Cuphead smiled as he watched this strange game in awe; the way those fellas threw the dice…reminded him of the ball games at the carnaval. Surely, this was a game right up his alley…right?

"Cuphead?!" Mugman called out. "Cupppheaddd! Where are you?!"

Mugman and Chalice walked into the casino mere seconds after Cuphead, and they were already lost in the crowd. It was so crowded that it seemed Cuphead was lost in a sea of casino patrons.

"Aw come on!" Mugman groaned in frustration. "We'll never find him at this rate! There's too many people!"

Chalice gave a smirk while cracking her knuckles.

"Don't sweat it, Mugsy. I got this."

Chalice quickly turned into her ghost form and dived into the floor in order to hide from the patrons. She then peeked through an upper wall to get a bird's eye view of the casino, the view of which was shocking.

"Yeesh, you'd think most people would stay away from a place like this, especially after what happened the past few months." Chalice thought. "Then again, gambling IS an addiction…a dangerous one. I better get Cuphead outta here, and fast!"

Chalice looked around from her spot, scanning the view for a teacup boy with a bright red bent straw and red shorts. Not too hard to find in this crowd, right?

It wasn't long before Chalice finally spotted Cuphead – throwing dice onto a table in a game of…

"Oh no, he's playing craps…" Chalice gasped. "I better warn Mugman and get down there!"

Chalice immediately phased through the wall on the way back to where Mugman was, not knowing that the Devil was watching from a reflected glass window (the type where he could see the crowd but the crowd couldn't see him).

Not only was he watching Chalice and Mugman helplessly trying to find their friend, but he also witnessed something even more interesting; Cuphead participating in the craps section…and winning.

"Of course that cup cannot resist my casino…" The Devil chuckled. "He has such a lack of self-control, it's hilarious. I think it's time for a reunion…"

With that, the Devil tapped his pitchfork to the ground, teleporting him to the casino floor.

Back with Cuphead, he was having the time of his life. A crowd gathered around the young cup to watch him throw one pair of dice after another…and once again winning the game.

"Holy smokes! He's winning again!"

One of the patrons turned to Cuphead with a shocked expression.

"Ya know how hard it is to get into a winning streak with this game? How do you keep winning?"

Cuphead looked at the patron and shrugged.

"It's not much different than throwing a ball." Cuphead explained. "The trick is to not overthink it."

Cuphead made another throw of the dice, winning another roll. The skeleton patrons were amazed as they chattered among themselves.

"Wow kid, you're a natural!"

"That he is…"

Cuphead and the patrons looked up to find an (semi)unexpected arrival; the Devil himself.

The young cup could feel every part of his soul go pale as the demon looked straight at him.

"The Devil?!" Cuphead exclaimed. "What're you doing here?!"

Suddenly, the Devil found himself snickering until he burst into laughter; how stupid was this kid?

"Why, I own this joint! Did you not read the sign, boy?"

Cuphead racked his brain…until he remembered Mugman reading the sign out loud.

"Ohh…"

Quickly realizing what potential danger he was in, Cuphead got off the stool he was using to become level with the table.

"Sorry to intrude." Cuphead chuckled sheepishly. "I'm sure my friends are goin' nuts lookin' for me, so I should go. Like now."

Cuphead then turned and dashed to leave, but suddenly the Devil teleported in front of him, blocking his path.

"Now hold on, kiddo. I never said you weren't welcome here."

The demon then wrapped an arm around Cuphead, who was visibly uncomfortable with the gesture. After all, he and his friends had really, REALLY bad experiences with him before.

"In fact, you're quite a hit at the craps table. Why don't we raise the stakes?"

That caught Cuphead's attention: what kind of stakes?

"Yeah?" Cuphead raised an eyebrow. "What're you proposing?"

With that, for some reason, some random jazz music started to play louder than usual. It started to play an eerie, melancholy melody (yet something we're all familiar with):

"Yes you recall, I'm the Devil…" The Devil sang in a solemn tone. "But there's no need to be judgemental…"

He then put both hands on Cuphead's shoulders as he gently led him back to the craps table.

"Let's forgo the past, make a deal with me…"

Cuphead flinched for a split second until he saw the Devil hold out a hand to him, a pair of glowing pink dice floating in front of him. He couldn't explain it, but he felt as though he was under a hypnotic trance.

"A lifetime of WEALTH…" The Devil finished, this time with a more menacing tone. "Is MY guarantee!"

Cuphead stared at the pink dice in awe; he'd never seen anything like them before, not even from the Devil.

"...wealth?" Cuphead gasped. "Like…money?"

"Indeed, my boy!" The Devil chuckled. "Win one more roll for me, and all the loot in the casino is yours. Lose…and your soul belongs to me."

The Devil held the dice even closer to Cuphead, whose eyes started developing glowing yellow dollar signs in his pupils, a more obvious sign of a hypnotic spell.

"Whaddya say, kid? Do we have a deal?"

Cuphead couldn't think twice before smirking at the Devil, snatching the dice from his hands, and walking back to the stool he was on.

"Ha! Watch me!"

Cuphead rolled the dice in his hands within an inch of his life, and he was about to take the throw. Until…

"CUPHEAD!"

Snapping out of his greed-induced trance, Cuphead immediately turned around to find a furious Mugman and Chalice standing next to the Devil.

"Mugsy? Chalice?"

"Cuphead, have you lost your MIND?!" Mugman scolded. "After everything we went through?! You know better than to take deals from..HIM!"

"But…he's saying we'll get rich if I do this!" Cuphead defended. "This could help us!"

"Cuphead, please!" Chalice pleaded. "Do you have ANY idea how dangerous it is to gamble with your SOUL!?"

Chalice glared daggers at the Devil, disgust filling her body at how quick he was to try to take advantage of her friend.

"I should know…I went through it myself."

Mugman immediately marched up to Cuphead, grabbed him by the arm and started to drag him away from the craps table, the latter still shocked by his brother's outburst.

"We're going home, right now!"

Mugman then shot the Devil a deadly scowl. Usually he'd be terrified, but he was willing to make an exception; especially to protect his brother.

"And YOU!" Mugman pointed his finger at the Devil. "You're gonna STAY AWAY from him! Or else!"

The Devil shook his head and laughed at Mugman's attempt at bravery.

"How cute, you think you're gonna protect your brother?" The Devil sneered. "I'm afraid he's not going anywhere…"

Satan then gestured to the craps table, the dice facing up; with two ones. Cuphead didn't realize it at the time, but he accidentally dropped the dice on the table during Mugman's attempt to drag him away.

"He's got snake eyes, which means…"

The Devil then turned red, a demonic grin plastered on his face as he extended his tail to grab a shocked Cuphead by the waist, dragging him to himself.

"HE LOST!"

Realising the severity of his actions (and how he got tricked again), Cuphead was furious.

"Hey, no fair! I didn't even throw the-!"

Before he could finish the sentence, a part of the Devil's tail wrapped around his mouth, preventing him from explaining himself.

"There's no talking yourself out of it this time, boy! Your soul is MINE!"

Mugman and Chalice watched with horror as the Devil immediately phased his hand through Cuphead's chest, quickly pulling his soul out of his body. The poor cup could feel all strength leaving his body, and his vision blacking out; it seemed all was lost.

Until…

"STOOOPP!"

Mugman dashed and stood firmly in between a weakened Cuphead and the Devil, who was really annoyed at being interrupted yet again while taking the cup's soul.

"Look, it's obvious you like making deals, right?" Mugman reasoned. "Is there some other way to escape this debt? We'll do anything!"

"Hmm…" The Devil paused. "Anything, you say?"

He released Cuphead from his hold and put his soul back into his body, the young teacup coughing and gasping for air as Mugman immediately tried to help him to his feet.

"There is perhaps one solution…" The Devil sang once more. "To resolve this confusion…"

The Devil then snapped his fingers to summon a parchment, with what appeared to be a list of names written on it. The paper floated down to Cuphead and Mugman, the boys looking at each other in nervousness.

"I have a list of Debtors…who owe me their souls…"

The Devil then loomed over the three cups, all of whom looked up in terror at what was happening.

"Collect 'em by midnight, or I TAKE ALL OF YOU!"

Wasting no time, the trio bolted toward the casino's exit, hearing the Devil continuing to sing behind them, the disembodied jazz music blaring once more.

"YES! They call me Old Scratch, Mr. S, the big D! I'm the King of the Underworld…and it's GREAT TO BE ME!"

The Devil cackled maniacally as the trio finally managed to exit the casino, parchment in hand, before the doors slammed shut behind them.

The three panted trying to catch their breath.

"Is everyone okay?" Chalice asked.

"Not entirely…" Mugman growled.

He then pointed a finger at Cuphead.

"What in the WORLD were you thinking, Cuphead?!" Mugman yelled. "You just put us into debt with THE DEVIL, AGAIN!"

"Hey! I didn't mean to drop the dice, Mugs!" Cuphead defended himself. "It was an accident!"

"Just like you 'accidentally' were about to THROW the dice?!"

Mugman facepalmed and squeezed his forehead; when was his idiot brother gonna learn his lesson?

"I can't believe you…after everything we went through, you've learned NOTHING!" Mugman scolded once more. "You're LUCKY Chalice and I were there! You coulda been killed!"

"Maybe you shouldn't have dragged me away!" Cuphead snapped back.

"Guys, that's ENOUGH!"

Chalice got in between the angry brothers, trying to diffuse the situation.

"Cuphead did something really, and I mean, REALLY stupid…but it doesn't matter now."

She took out the list the Devil gave them and showed it to the brothers.

"What the Devil asked of us is hard to swallow. We should seek guidance from someone way more experienced than we are…any ideas?"

At that, Cuphead had a lightbulb on top of his head.

"Quadratus! He's helped us before with the Devil, maybe he has some advice for us!"

"That's a good start!" Chalice agreed. "Let's start heading over there!"

With that, the trio dashed off toward their home, which wasn't far away from where Quadratus was located.

A/N: Whew, sorry if this chapter was super long, but I needed to establish the story in one chapter so I can go straight into the debtor's stories. Feel free to lemme know your thoughts in the comment section!