- “Most everyone's mad here. Aha... HAHAHAHAHA!! You may have noticed that I'm not all there myself.”
- ―Cheshire Cat
The Cheshire Cat has a permanent smile on his face and can disappear at will. He is a very odd being able to reshape his body to either amuse or frighten his visitors. He's very mysterious, and in his own way, very dark. Like all members of Wonderland, he is mad, but unlike the others, he admits it with pride. All of Wonderland's inhabitants appear to hold a fear over him, even the Queen of Hearts, most likely due to the fact that he is the maddest and craziest of them all, or it could be due to his unique abilities.
His true nature in the film is highly questionable, but above all, he appears to be a completely neutral character. In many instances, he's the only being in Wonderland to show kindness and sympathy towards Alice, giving her advice on which path to take during her journey, practically acting as her wise guide to the point where she's overly joyous to see him once he returns. On the other hand, the cat has a cruel sense of humor, as seen during the meeting with the Queen of Hearts where he constantly caused mishaps to purposely have the Queen's dangerous temper target Alice. This behavior carries out up into the climax, though it can be slimly argued that he caused the Queen's temper to violently erupt for the last time to assist Alice in getting home, as the climactic chase throughout Wonderland eventually leads to her awakening, as it was all just a dream, which would mean he knows everything that is happening around Alice and possibly what's going to happen ahead of time.
After a gamut of nonsensical events in a 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 passageway 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 Dormouse, 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.
The Cheshire Cat has numerous non-speaking appearances in House of Mouse. He also appears in Mickey's House of Villains, but wasn't a part of the villains that take over the club. This clearly means that in the film, he wasn't one of the villains.
In "The Stolen Cartoons", when Donald Duck proved to be a terrible host, the Cheshire Cat vanished from the club. In "Big Bad Wolf Daddy", he was blown away leaving only his grin behind during the wolf's performance. In "Ask Von Drake", he was seen atop the Queen of Hearts' crown during "The Ludwig Von Drake Song". In "Unplugged Club", when Pete took out the club's battery, only his eyes and grin showed in the darkness. In "Super Goof", he could be seen atop the March Hare's chair with the Mad Hatter pouring tea on the Hare. In various episodes such as "Mickey and Minnie's Big Vacation", he could be seen clapping in a crowd with other characters when a cartoon has ended.
The Cheshire Cat can be briefly spotted during the final scene of the film Who Framed Roger Rabbit. His tail and also half of his face and body can be briefly seen during the final shot.
The Cheshire Cat was a supporting character in the 1995 series. He loves to play all manner of practical jokes on everyone, but even he occasionally performs some act of kindness.
Originally a friend of Alice, the Cheshire Cat appears many years later when she returns to Wonderland, now wild, ferocious and apparently loyal to the Red Queen, in addition to being one of a monstrous size.
The Cheshire Cat encounters his "old friend" in Tulgey Wood and attempts to eat her due to a lack of food within the woods. However, he is distracted by the Knave of Hearts and accidentally swallows a mushroom, causing him to shrink to the size of a house cat, prompting him to flee.
Video game appearances
In the Alice in Wonderland stage, the Cheshire Cat's grin was among the obstacles that appear in the maze as the player seeks out Alice's missing head and back. Despite this, the Cheshire Cat's image was among the heros on the door to the storybook, confirming that he is one of them.
The Cheshire Cat appears in several games of the Kingdom Hearts series, although most of them are minor as they take place in Wonderland. However, in Kingdom Hearts, his intentions appear to be ambiguous as he appears as either an ally or an enemy; he helps Sora during his visit to Wonderland, but also summons a Trickmaster Heartless against the group, although it appears he simply wants to test Sora towards these obstacles.
In the HD re-release of Kingdom Hearts Re:coded, Cheshire Cat played his first speaking role, assisting Sora in recovering Alice's memories, which went missing due to the digital world of Wonderland becoming corrupt at the hands of a bug infection.
The Cheshire Cat briefly appears during the Alice in Wonderland mini-game during the player's free-fall down the rabbit hole.
In the game, the Cheshire Cat is one of the many Disney characters kidnapped and taken to the Wasteland world of illusion, where an evil witch named Mizrabel plans to steal the essence of famous Disney characters to gain access to their world and dominating it. After Alice (who was also kidnaped) is rescued, she gives Mickey Mouse (the hero of the story) the quest to find the Mad Hatter and the Cheshire Cat.
The Cheshire Cat appears in audio-animatronic form in the Alice in Wonderland dark ride, in the Tulgey Wood scene. He also appeared in the ride's finale as a giant head just before the Mad Tea Party scene, but was removed from it during the ride's 2014 refurbishment.
The Cheshire Cat also appears during World of Color's finale. In the show, his animated face is seen in the water projectors, while the rest of his body is made completely of water.
In Disney's Electrical Parade, the Cheshire Cat appears with Alice on his back. During the parade, he demonstrates his powers by continuously disappearing leaving only his mouth, eyes, and nose in sight.
A statue of Cheshire Cat can be spotted in Alice's Curious Labyrinth. His grin is also featured in the attraction's garden.
In the park, the Cheshire Cat appears briefly during Alice's segment of Disney in the Stars.
- The Cheshire Cat was used as inspiration for the character Chaos in the Aladdin TV series as well as the Talking Zebra in Phineas and Ferb.
- The Cheshire Cat is the third Disney character originally voiced by Sterling Holloway and taken over by Jim Cummings. The first two are Winnie the Pooh and Kaa.
- When Alice first hears the Cheshire Cat, he is singing the first and last stanza of the poem "Jabberwocky".
- Originally, the Cheshire Cat was supposed to sing a song called "I'm Odd" but was later replaced with "Twas Brillig". For the Alice in Wonderland: Special Edition DVD it was remastered and sung by Jim Cummings as the Cheshire Cat.
- In Epic Mickey, the Cheshire Cat was going to appear in the game at the level "Wonderland". But he and the level were scrapped in the final because Warren Spector didn't want to cause confusion with the Tim Burton retelling, which was going to come out at about the same time.
- In Cinderella, Lucifer appears to share some similar physical properties with the Cheshire Cat: they both are rather fat in appearance, they both have a rather large grin at most points, and both have rather sharp claws. However, while Lucifer is evil, doesn't talk, and has black fur and cat fangs, the Cheshire Cat is more neutral and sometimes good, has the ability to talk, and has pink-and-purple striped fur and regular molars. This may be because the two films were produced next to each other (1950 and 1951).
- The original Cheshire Cat was based on an actual cat breed, the British Shorthair. It may have provided some inspiration for Disney's Cheshire Cat.
- The Cheshire Cat originally lacked a voice actor in the Kingdom Hearts series, but was finally voiced by Jim Cummings in HD 2.5 ReMIX.
- In the book, the Cheshire Cat is brown and tan colored.
- Bing Bong's tail looks similar to the Cheshire Cat's.
- The only time the Chesire Cat was shown not smiling was when he was gasping from his mad laughter.