Ms. Chalice's girl group has been spotted by two famous actresses with whom we are all familiar, due to them looking for helpers in their latest movie. The Cup Brothers joined in the volunteering, but the actresses have taken a shine in them, which enrages Chalice and Cora with envy that they even plot to kill them. Can it get worse?

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?

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.

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.

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.

The Cup Trio were about to watch the Inkwell Races until the Devil showed up for Cuphead's soul again. However, this made him and Cuphead end up hit by a truck, taken to the hospital, and bedridden due to their broken right legs as they share a room with a lion angel who holds a grudge against the Devil as Mugman and Chalice try to get to Cuphead.

What was supposed to be a relaxing shopping day at the Farmer's Market turned into another troubling adventure when Cuphead's head got taken by a flying bird and landed in the area of Baroness Von Bon Bon, a "sweet" lady with a head collection. With Mugman and Ms. Chalice helping his headless body, they go on a quest to save Cuphead's head and avoid getting their heads removed too.