It is not so much the titles of Shakespeare's plays as it is their thematic content that is significant to the plot of Wednesday Wars. In Mrs. Baker's words, Shakespeare
"wrote to express something about what it means to be a human being in words more beautiful than had ever yet been written."
The plays that Holling studies with Mrs. Baker include The Merchant of Venice, The Tempest, Macbeth, Romeo and Juliet, Julius Caesar, The Tragedy of Hamlet, Prince of Denmark, and Much Ado About Nothing. From each of the plays, Holling learns something about the human condition which helps him grow into maturity.
In Merchant of Venice, Holling is able to perceive that Shylock, usually looked upon as a villain, is a victim himself. The tragedy of Shylock's situation is that he cannot become whom he is supposed to be because others will not let him. Holling is able to look at his father with "the quality of mercy" because of this realization, understanding that perhaps his father is callous and ruthless because that was what had been expected of him, and he never had a choice. Holling does not want to end up like his father; he does not want to be, like Romeo from Romeo and Juliet, "Fortune's fool." Holling wants to choose for himself, to have "the chance to see what (he) can do with the slings and arrows of outrageous fortune." Hamlet, from the play of the same name, never got that chance, because he waited too long to take charge of the things happening in his life. Warned by Hamlet's example, Holling learns the importance of making decisions and acting upon them in a timely manner, before the opportunity passes him by.
Holling gleans a great deal of wisdom from his reading of Shakespeare, wisdom that holds him in good stead as he grows towards young adulthood. Mrs. Baker is very hopeful for his future, comparing him to Don Pedro in Much Ado About Nothing. She believes that Holling, like Don Pedro, will become
"a man who (brings) peace and wisdom to his world, because he (knows) about war and folly...love(s) greatly, because he (has) seen what lost love is...and...(comes) to know, too, that he (is) loved greatly."