How we cite our quotes: All quotations are from Good Will Hunting.
Quote #4
MAGUIRE: You're a tough kid. I ask you about war, you'd probably uh... throw Shakespeare at me, right?
As his speech continues, Maguire keeps listing all of the things that Will has only experienced through books. His basic point is that there's a whole lot of stuff in life that you can't learn from books. There's a lot that you can only learn firsthand, and this is the stuff that Will needs to go out and expose himself to.
Quote #5
MAGUIRE: I look at you: I don't see an intelligent, confident man. I see a cocky, scared s***less kid.
Finally, Maguire tells Will what he really thinks of him. Will thinks everyone sees him as a genius, but Maguire only sees a cocky scaredy-cat. He never argues for a second that Will isn't a genius because it's clear that he is. But he wants Will to put more focus on the stuff he doesn't know.
Quote #6
MAGUIRE: You're an orphan, right? Do you think I'd know the first thing about how hard your life has been, how you feel, who you are because I read Oliver Twist?
To help Will see his point, Maguire turns the tables on him and asks how he would feel if Maguire pretended to know about his experience as an orphan just from reading Oliver Twist. This point seems to hit home with Will, and in a way, it marks the beginning of his real growth into adulthood.