How does Shakespeare help Holling with his classmates in Gary Schmidt's 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.