The Cheshire Cat

The Cheshire Cat is one of the cats of Auradon. He is mentioned in the Descendants: Wicked World episode, "All Hail the New Q.N.L.B", when Evie suggests the "cheshire cat eye" makeup for Audrey. His grin appears in the episode "Mad for Tea".

Alice in Wonderland
After a gamete of nonsensical events in pursuit of the White Rabbit, Alice enters the Tulgey Wood. There, the Cheshire Cat arrives offering her help with directions. She tries to receive practical answers, but he continues to goof off by asking random questions, and continually showcasing his abilities. After a while, he advises her to seek answers from the Mad Hatter and the March Hare. She, not wanting to associate with mad people, denies the advice, but he claims that everyone in Wonderland is mad, including himself. He then slowly fades away into thin air, laughing and singing in the process.

Later on, Alice finds the trail of the White Rabbit once again, and begins to pursue him once more. She is lost again, but this time, all hope seems lost. She breaks down in tears, just when the Cheshire Cat arrives. Delighted to see him, she claims that she's no longer looking for rabbits, and wants to find her way home. However, he explains that in Wonderland, she has no way, and that all ways there are the Queen's ways. Confused, she informs him that she knows nothing about the queen, so he reveals a secret passage way to her card-inhabited kingdom.

During a croquet game with the Queen of Hearts, the Cheshire Cat arrives and continuously gets Alice into trouble with the Queen. At one point, the Cheshire Cat causes the Queen to flip over, revealing her bloomers. Out of utter embarrassment, she puts Alice on trial. With the witnesses being the Mad Hatter, March Hare, and the Doormouse, the trial gets nowhere. Soon enough, the Queen sentences Alice to death by beheading, until she finds more mushrooms in her pocket, which causes her to grow to a gigantic size. She then takes advantage of the opportunity and insults the Queen, but she shrinks down to her normal size once again. The Cheshire Cat appears once more, repeating Alice's insults which causes the Queen to lose her temper, and this leads to the climactic chase.

Trivia

 * He was voiced by Sterling Halloway in his debut, who later voiced Kaa in The Jungle Book.