Just some Cuphead headcannons - Boss Souls
Goopy - Sold his soul to live beyond the grave. Literally.
Ribby and Croaks - Bet the devil they could win a fight with his best boxer. Both lost and were put in dept.
Hilda Berg - Unable to fly after a terrible crash landing. Sold her soul to fly again.
The Root Pack - Sold their souls to win ‘Largest Carrot/Potato/Onion’ prize at the county fair.
Cagney - Taken advantage of for looking like a cute wimp. Sold his soul to become scary. When he wants.
Baroness Von Bon Bon - Beheaded by rebels. Sould her soul to get her castle back.
Djimmi the Great - Sould his soul to no longer be bound by his lamp.
Beppi the Clown - Didn’t make the devil laugh at his brithday party. The Devil took his soul as payment.
Grim Matchstick - Devil made him guard a hoard. Didn’t want to hurt the looters, and gave the devil his soul instead.
Wally Warbles - Originally a sentient clock. Sold his soul to become a real bird.
Captain Brinebeard - Stole a living ship from the Devil. Payed with his soul.
Phantom Express - A train owned by the Devil in general to house lost souls. Eventually went off the rails, so to speak.
Rumor Honeybottoms - Originally a bee under an evil queen. Sold her soul to usurp her and modernize the colony.
Cala Maria - Sold her soul to become beautiful and not petrify people.
Sally Stageplay - Sold her soul for fame.
Dr. Kahl’s Robot - Wanted a soul. Devil let him have one that was to be returned to him at a later date.
Werner Werman - Sold his sould to defeat his arch enemy, and turn him into a robot.
King Dice - Amassed Gambling Depts at a young age. Sould his soul to turn the depts around and buy the Casino.