Follow the misadventures of the impulsive scamp Cuphead, his cautious, but easily swayed brother, Mugman, and their adventitious, hard working, and reckless friend, Red Rose. As they explore Inkwell Isles with fun, adventures, and try to get themselves out of trouble, but trouble isn't far behind, especially with the Devil on the scene to make life tough for them.

Evelyn and her group of friends were on there way home when they wake up in a cartoonish world where everything is cartoony! Now the gang must find out how to get back home. They run into two cup brothers and there begins their adventure, meeting friends and foes.. but will they be able to go home or is there a worse fate instore for them?

Gwen is an 18-year old who dreams to be free from her parent's restriction during the Great Depression and choose her own path. After picking up a magical artifact that she found that gave her incredible powers, she is kidnapped and brought to the Inkwell Isles to be the Devil's bride. After escaping the underworld, she befriends two cup brothers and bring her on their adventures.

When the three dangerous Batderson Sisters landed on Inkwell Isle's and threaten to eat all the children's souls Alicia, Blood, Gemma and the three cups Cuppy, Cuphead and Mugman must stop them.

A young girl sets out to discover the world for the first time with an unexpected friendship with two brothers as they get into adventures and mischief as she learns to be wary of strangers especially when one happens to be the Devil himself. (Ch 5 Up!)

In the classic tale as old as time, two brothers became prisoners of a cursed princess. After bonding with the enchanted staff, they learned to find beauty within the darkest of creatures. But with time against them, the beast and the staff must put their faith on the brothers and hope that one's love is strong enough to break their curse before the last rose petal falls.

Through a magical parchment role, the Royal Wizard Blood lands in the Cartoon World of Inkwell Isle's. With the help of the two brothers Cuphead and Mugman Blood has to prove itself not only normal problems. The Devil seems to be very interested in the Wizard and his powers and homeworld.

After the events of Handle With Care, Mugman runs into Bowlboy again and, feeling bad for snapping at him, decides to apologize.

While having fun at the Sea Fair, the Cup Brothers run into Ms. Chalice, who seeks their help to help an old acquaintance of hers. This person is on a treasure hunt for the Treasure of Blue Belle Island. But the Cup Trio and their alley adventured through the island; the Devil tried to sneak away from King Dice and Henchman to go after Cuphead's Soul again.