How does Holling feel about his role in the Shakespeare play in The Wednesday Wars?

The Wednesday Wars is full of so many great sequences that are likely to have many readers laughing out loud. Author Gary Schmidt does a wonderful job of capturing the thoughts and emotions of a junior high student, and Holling is a joy to follow.

Holling Hoodhood finds himself a slightly unwilling participant in Mr. Goldman's presentation of The Tempest. Holling only agrees to be in the play because it allows him to get the replacement cream puffs for next to no money at all. Unfortunately, those cream puffs are also ruined. Just after the two rats destroy the cream puffs, Holling returns to Mr. Goldman to pick up his copy of the script.

This is where you can find the answer to your question, because Holling plainly explains how he is not excited to be in the play. Holling first explains that he isn't thrilled about his part, because he is playing Ariel. Ariel is a fairy, and Holling makes it clear that being a fairly won't end well for a junior high boy. Holling even says that he can't play the part. Mr. Goldman completely ignores Holling's request and hands Holling his costume, and that's when we see that Holling really doesn't want to be in the play. He has to wear bright yellow tights ... with feathers on the backside. Holling will repeatedly question the wisdom of his going through with the part, and the way that he focuses on the yellow tights with butt feathers is simply hilarious every time.

In "The Wednesday Wars" by Schmidt, when does Holling start reading Shakespeare?

Holling's introduction to Shakespeare comes right after the Great Chalk Dust Cream Puff Caper, in other words, right after Holling's inadvertent destruction of three trays of newly baked cream puffs. Mrs. Baker was trying in vain to find a productive use for Wednesday afternoons during which she and Holling's are marooned together since half the classes goes to Catholic and the other half to Hebrew lessons. Holling is the only Presbyterian and left in the care of Mrs. Baker.

"Hoodhood," she said quietly. She thought for a moment. Does your family attend Temple Beth-El?" she said. ... "Saint Adelbert's, then?" She asked this kind of hopefully. ... "[On] Wednesday afternoon your attend neither Hebrew School noe Catechism. ... You are here with me." ... Mrs Baker looked hard at me. I think she rolled her eyes.

One of her efforts at occupying Wednesday afternoon came in the form of chalk eraser cleaning. This ill-fated plan was unhappily inaugurated on the same day that Mrs. Bigio handed over dozens of fresh cream puffs to Mrs. Baker for transport to the Wives of Vietnam Soldiers (WVS) meeting. Chalk dust, liberated from the erasers, wafted up the levels of the school building, lingered outside the one set of open windows--left open with a noble purpose related to keeping cream puffs from getting soggy--then wafted in at the window and, obeying gravity, settled decoratively across all the dozens of cream puffs. The women of the WVS were unhappy with their cream puffs that night.

The cloud of dust had drifted in, and then gravity had taken over. The chalk had fallen gently upon each of the cream puffs.

Following this, Mrs. Baker decides to take a different tack, one with less physicality and danger attached to it: She and Holling will begin reading Shakespeare on Wednesday afternoons. This all works out well for Holling as he discovers that Shakespeare is full of witches, murders, drunkenness, wizards and spirits--who could resist?  You'll find where Mrs. Baker unveils her great idea on pages 39 and 40 in the Sandpiper, Houghton Mifflin Harcourt 2007 hardcover edition. You'll find where she pulls out two musty books from her desk drawer, dusts them off, leaves the dusty musty smell behind, and hands one to Holling while keeping the other for herself, commencing their Shakespearean readings together to be sure Holling is "following the dialogue," on page 46.

How does Shakespeare help Holling with his classmates in The Wednesday Wars?

When Holling begins studying Shakespeare in Gary Schmidt's The Wednesday wars, at first he only starts relating his classmates to the villainous characters found in the plays because of his insecurities. Doing so makes him feel like he has some sense of understanding of who his classmates are as people. However, as Holling continues to study Shakespeare, his knowledge of Shakespeare begins helping him draw closer to his classmates, helping him to make actual friends.

Holling especially begins relating his classmates to Shakespeare's villains when his classmates start giving him death threats if he doesn't procure cream puffs for the whole class. For example, in a dream, Holling sees Danny Hupfer as Caliban, a monster from The Tempest, sitting on the edge of his bed and threatening that Holling would end up "all scurvy and blistered" if he doesn't bring the cream puffs ("November"). Holling relates Danny to Caliban because Caliban is a violent antagonist in The Tempest, and Danny is able to give the bloodiest, most creative death threats. However, by December of the story, Holling's view of his classmates changes, and his knowledge of Shakespeare plays a significant role.

In December, Holling agrees to play the role of Ariel from The Tempest in a Shakespeare extravaganza for the reward of cream puffs purchased cheaply. For the role, Holling must wear a humiliating costume of bright yellow tights decorated with white feathers on the backside. The same night of his performance, Mickey Mantle is signing autographs in the Baker Sporting Emporium. Holling has just enough time after the play to make it to the Emporium. But when he shows up dressed in his fairy costume, Mantle refuses to sign his ball, saying he doesn't "sign baseballs for kids in yellow tights." Danny, who had just seen Holling's performance as Ariel, witnesses Mantle insult Holling and decides to return his own newly signed ball. Bravely, Danny puts down his own ball and says to Mantle, "I guess I don't need this after all," and calls him a "pied ninny." Danny does so because he respects Holling and knows it is wrong of Mantle to insult Holling for wearing a Shakespearean costume. It's at this point that Holling and Danny become best friends. Since Danny respects Holling for his knowledge of Shakespeare and his brave ability to perform it so well, this scene shows us that Holling's knowledge of Shakespeare is beginning to shape and change his relationships with his classmates.

What does Holling learn about Shakespeare in The Wednesday Wars?

An important lesson that Holling learns from Shakespeare is that

"it's hard to care about two things at the same time - like caring about the Montague family and caring about Juliet too."

Holling, of course, learned this lesson about the human condition from reading Shakespeare's Romeo and Juliet. Holling is unable to understand this lesson until he experiences something similar in his own life, in relation to his friend Meryl Lee Kowalski. Meryl Lee and Holling are just beginning a relationship when Meryl Lee's father steals an idea of Holling's father which Holling had innocently shared with Meryl Lee. When Holling discovers what has happened, he is at first furious with Meryl Lee, ignoring her assertion that she had no idea that her father would do such a thing. Holling does not believe Meryl Lee, and also does not see how hard it is for Meryl Lee to love her father even though he has betrayed her and Holling, and to love Holling at the same time. It is only when Holling sees the connection between what Meryl Lee is going through and what Romeo goes through, loving his family and loving Juliet at the same time, even though his family, the Montagues, hates Juliet and her family, the Capulets. Shakespeare's lesson in Romeo and Juliet helps Holling understand the position that Meryl Lee is in, and enables him to be compassionate towards her in her despite his own discomfiture (Chapter 6 - "February").