On Inkwell Isle,the two brothers,Cuphead and Mugman lives with Elder Kettle. While they're out,The brothers ended up in the Devil's Casino and begin playing craps. When they go on a winning streak,the Devil appears and makes a deal,threatening to take their soul if they lose. Despite Mugman's begging,Cuphead accepts the offer but loses by rolling snake eyes. The brothers beg for mercy,so the Devil offers them another deal to have them collect the soul contracts from his runaway debtors by midnight the next day,the Devil might spare them.

The Brothers returns home to tell Elder Kettle about their situation,so he gives them a potion that allows them to fire blasts of energy from their fingers and warns them that the debtors may not turn their souls contracts willingly. The Brothers met ,who agrees to help them. They manage to defeat each debtors in order to obtain their contracts. Back at the Casino,Cuphead,Mugman,and Chalice meets with King Dice,who wants to stop them,saying their success has caused him to lose the bet. After they defeated him,The Trio confronts the Devil,who reveals that Chalice has been a runaway debtor all along.

The Brothers defends Chalice and battle against the Devil and defeats him. They incinerate the contracts and return home. Learning that they have nothing to fear from the Devil anymore,the former debtors honor the brothers for their heroism.