Through the character of Iggy and his escapades, The Best of Iggy delves into the challenges of growing up. At nine years old, Iggy is encountering many difficulties typical of childhood, and his rebellious nature drives him into all sorts of trouble.

During the first episode, Iggy becomes jealous of Jeremy Greerson, whom everyone perceives as “the most wonderful boy in the world” (18). When his younger sister, Molly, asks Jeremy to read to her, an activity that Molly and Iggy usually do together, Iggy feels as if Jeremy is replacing him, and this feeling is compounded by the suspicion that his parents wish he were more like Jeremy. Iggy’s sense of self is still developing, and Jeremy’s seeming perfection feels like a threat, which causes Iggy to lie about having jumped off the roof before: “Iggy intended to make Jeremy feel bad that he wasn’t as brave as Iggy” (32). Iggy merely intends to impress Jeremy, but this lie has an unintended consequence: Jeremy wants to jump off the roof himself, which the adults blame on Iggy. This incident illustrates how jealousy can create challenges for young people.

In the second incident, Iggy struggles with authority, another part of growing up.