Among the caterpillars who appear as literary characters is the famous caterpillar from Alice in Wonderland that Alice manages to insult. Illustrating caterpillars as characters who interact with humans is difficult. Caterpillars do not have human-like eyes, an important feature to communicate feelings. Caterpillars have 3 pairs of short legs next to their head. Drawing caterpillars holding anything is challenging.The original drawings for Alice in Wonderland were by cartoonist, John Tenniel. Tenniel was famous as a political cartoonist for Punch. Blind in one eye, Tenniel memorized his characters and drew from memory. He must have spent some time studying caterpillar form because he gets a number of features correct, including the placement of the legs, the prolegs and the shape of the head. The style of his illustrations has influenced later illustrators of Wonderland characters.
Tenniel resolved the difficult problem of facial expression by placing the point of view at an angle behind the caterpillar so that the head is obscured.
How the caterpillar would hold the hookah was another problem. For this, Tenniel added a human-like arm and hand to the side of the caterpillar, partially obscured by a cloth. Pure fantasy, but so is the book.