Baroness Von Bon: A kingdom of candy
Von Bon, as a kid, never got to eat candy. Her parents denied it due to excess sugar and her hyperactivity. That pent-up withdrawal made her grow into a candy-obsessed madwoman—and that's before the Devil offered her something real sweet: a kingdom of candy all for herself. Anyone can eat it, but she is a zealot, so she won't exactly share.
Beppi the Clown: Clients for his park
Let's be real—even if the park is the best in the world, a mascot like Beppi would cause anyone to run away. That caused his park to collapse in bankruptcy. Looking for money and to get some audience that loved him, he made the deal for the sake of his park and being loved. Sadly, he came to be loved... by utter cretins.
Djimmi the Genie: No deal
Fearing a wish-granting genie would make people stop making deals, King Dice decided to seek the lamp of the genie. His three wishes were:
- No more wish granting
- The wish can only be reversed by his (King Dice's) defeat
- And he will defend both as long as the Devil still has the contracts
Wally Warbles: To be able to care for himself and his son
Wally is the only boss with a sort of family shown—in this case, his son, but no wife. Maybe
a cooked bird appears let's not think about it. The point is that, following that, Wally asked the Devil for his son to be able to defend himself in case he wasn't able. As seen in his fight, said power was giving his son a powerful mind—which makes you wonder, since he is one of the many bosses that doesn't reappear in the ending, and considering his state...
shudders
Grim Matchstick: Friends
Easily the most tragic contractor. Grim has been alone since hatching. Being a humongous dragon that spits fire hasn't helped. Said loneliness evolved into stuttering, which made it even harder to communicate. Sad and alone in a huge castle he couldn't share with anyone, he literally sold his soul to have anyone to talk to. In a bit of extra cruelty, the Devil decided his power as a dragon could grant him a powerful guard dog for free, so he granted him two heads that were friends—but toxic ones—encouraging him into releasing his pent-up frustration onto anyone that dared to defeat the Devil. His kind side still remains, though—hence why his game over quotes are from apologies to begging the brothers to flee.