What is Ponyboy comparing Two-bit to when he calls him a Chessy cat in the book The Outsiders?

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Two-bit is compared to a “Chessy cat,” the malevolently grinning Cheshire Cat from Alice in Wonderland.  Two-bit is grinning because he pulled a prank.

In this allusion to Alice in Wonderland, Two-bit is described as grinning in a self-assured, at-your-expense way.

I looked fearfully over my shoulder and there was Two-Bit, grinning like a Chessy cat. (ch 2)

Two-bit sneaks up on Johnny and Ponyboy and pretends to be a Soc to scare them.

The Cheshire Cat is a particularly sneaky grinning cat that Alice encounters, but the term did not originate with the book.  In fact, to grin like a Cheshire cat is actually British slang dating to the 18th century.  The term “Chessy cat” is an American amalgamation of the term based on the popular children’s book.  Either way, it implies being very happy about something and most likely at someone else’s expense.

The allusion to literature is fitting both as teen slang and as a literary allusion. Ponyboy is an avid reader and highly intelligent, so it makes sense that he would have read Alice in Wonderland.  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.

 

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While Pony and Johnny are at the drive-ins sitting next to the two Soc cheerleaders, Cherry and Marcia, Two-Bit sneaks up behind both boys and grabs their shoulders. Two-Bit then pretends to be a Soc and threatens Pony and Johnny, who are instantly startled and afraid. After Pony and Johnny jump out of their seats in terror, they turn around to see Two-Bit smiling like a "Chessy cat." Ponyboy is alluding to Lewis Carroll's classic character the Cheshire Cat of Alice in Wonderland. The Cheshire Cat is a mysterious creature in the story, famous for his enormous grin. The Cheshire Cat's body can even disappear, leaving only his grinning teeth behind.

The fact that Pony alludes to a classic work of literature characterizes him as an intelligent, astute adolescent who enjoys reading and is familiar with classic works of literature. Pony's intelligence and affinity for reading set him apart from the other Greasers, who struggle in school.

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In chapter 2, Ponyboy and Johnny are sitting beside two Soc cheerleaders watching a beach movie when Two-Bit comes up from behind them and scares them by saying, "Okay, greasers, you've had it" (Hinton, 25). Pony instantly turns around to see Two-Bit smiling like a "Chessy cat." Ponyboy utilizes two literary devices in his comment when he refers to Two-Bit as a "Chessy cat." Pony utilizes a simile, which is a comparison between two different things using the words "like" or "as." Pony also utilizes a literary device known as an allusion, which is a reference to something with a historical or cultural significance. The Cheshire cat that Ponboy refers to is a character in Lewis Carrol's 1865 novel Alice in Wonderland, which was later recreated in a popular film by Walt Disney in 1951. In the animated film, the Cheshire cat is continually grinning, which is exactly what Ponyboy is referring to when he turns around to see Two-Bit smiling behind him.

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Ponyboy likens Two-Bit to grinning like a "Chessy cat" after he scares Johnny and Ponyboy at the Nightly Double Drive-in movie theater.  Ponyboy's use of "chessy cat" is a literary allusion, which means he referenced content from some other literary work.  In this case, Ponyboy was referring to the Cheshire Cat in Alice and Wonderland, of which the animated Disney version debuted in the 1950s and its hallmark mischievous, grinning purple cat was widely known and referenced at the time.  Hinton makes use of two different types of figurative language, incorporating both simile and allusion, to make the moment both memorable and believable.

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Yes, this is a simile, and it is also an allusion. I have been asked this question several times by students when I taught The Outsiders, and none of them had a clue what the term meant. The "chessy cat" to which Ponyboy refers is a character created by Lewis Carroll in his fantasy classic Alice's Adventures in Wonderland (thus, the allusion). The Cheshire Cat is best known for its "mischievous grin"--like Two-Bit's--and the cat also had the ability to disappear at will; upon vanishing, the grin was the last part of its body to be seen. Carroll did not originate the idea of the grinning Cheshire Cat; it had been referenced at least 100 years prior to Carroll's writing Alice's Adventures in Wonderland.

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When Ponyboy refers to Two-Bit Mathews "grinning like a Chessy cat" in Chapter 2 of The Outsiders, he is no doubt using an allusion referring to the mythical Cheshire cat made famous by Lewis Carroll in Alice's Adventures in Wonderland. The Cheshire cat in Alice was famous for its mischievous grin but, nearly as important, it could appear and disappear at will. In this scene of The Outsiders, Two-Bit surprised Pony when he came out of nowhere and snarled, "Okay, greasers, you've had it." Pony "almost jumped out of his skin" until he "fearfully" looked back to find it was only Two-Bit. Two-Bit was also similar to the Cheshire cat in another way: The cat in Alice often cheered her up when she was down, just as Two-Bit does with Ponyboy.

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The Cheshire cat in Alice's Adventures in Wonderland by Lewis Carroll is famous for its puzzling smile. When Ponyboy calls Two-Bit a "chessy cat," Two-Bit is smiling at him in an ironic way. To say that someone is a Cheshire cat is a metaphor because it is equating two essentially unlike things (one thing is another, when we know it's not really). To say that the person is smiling like a Cheshire cat is a simile. Similes are comparisons that use the words "like" or "as."

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When Ponyboy says that Two-Bit is "grinning like a Chessy cat", he is comparing him to the character of the Cheshire Cat from the Lewis Carroll story Alice's Adventures in Wonderland.  The Cheshire Cat is a feline with the magical ability to become invisible except for his toothy smile; oftentimes in the tale, the large grin is all that can be seen of him.  Two-bit, who has just played a prank on Ponyboy and Johnny by impersonating a threatening Soc, is grinning from ear to ear, and his demeanor reminds Ponyboy of the famous cat from Wonderland. 

Ponyboy's use of the allusion and while mispronouncing the term (Cheshire/Chessy) illustrates through marvelous juxtaposition the two opposing and seemingly contradictory sides of his nature.  Ponyboy is a tough, unrefined member of the Greasers from the wrong side of the tracks, but at the same time he is highly intelligent, studious, and well-read.

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