Two-bit is grinning because he pulled a prank. Two-bit is compared to a “Chessy cat,” the malevolently grinning Cheshire Cat from Alice in Wonderland. … Why does ponyboy call two bit a chessy cat? He had a grin on his face like a Cheshire Cat. If someone is grinning like a Cheshire cat or like the Cheshire cat, they are smiling very widely. What does calling someone a chessy cat mean? He stole two packs from a corner store before taking Ponyboy and Johnny to the nightly double. What do they call cigarettes in the outsiders? , what does chessy cat mean in the outsiders Most readers are also familiar with the book, and the sneaky Cheshire Cat, and will likely accept Two-Bit’s sneaking up on Ponyboy and Johnny. Ponyboy is an avid reader and highly intelligent, so it makes sense that he would have read Alice in Wonderland. The allusion to literature is fitting both as teen slang and as a literary allusion. Either way, it implies being very happy about something and most likely at someone else’s expense. The term “Chessy cat” is an American amalgamation of the term based on the popular children’s book. In fact, to grin like a Cheshire cat is actually British slang dating to the 18th century. The Cheshire Cat is a particularly sneaky grinning cat that Alice encounters, but the term did not originate with the book. In this allusion to Alice in Wonderland, Two-bit is described as grinning in a self-assured, at-your-expense way. What does chessy cat mean in the outsiders – Two-bit is compared to a “Chessy cat,” the malevolently grinning Cheshire Cat from Alice in Wonderland.
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