- David's Mom: When your father was here, I used to think, "This was it. This is the way it was always going to be. I had the right house. I had the right car. I had the right life."
- David: There is no right house. There is no right car.
Jane Kaczmarek - David's Mom
Tobey Maguire - David

“- Jan: Where are your mom and dad?
- Christopher McCandless: Living their lies somewhere.”
Catherine Keener - Jan
Emile Hirsch - Christopher McCandless

“You and Ursula together would be unbefitting to her social stature, you see? Let me put it in the way you might understand. Where you come from, zebras marry zebras and leopards marry leopards. Stripes for stripes. Spots for spots. Ursula is a stripe and you are a spot. One which I intend to have removed as soon as possible.”

Holland Taylor - Beatrice Stanhope

“You don't know anything about society, Maria; you don't have the satisfaction of avoiding it.”

Michael Douglas - Nicholas Van Orton

“- Jeff Kohlver: I'm a decent guy. Ask anyone. Go ahead. Ask these models.
- Hayley Stark: Of course they will. You're not an idiot. You don't piss where you live. Those girls were your work, and I, on the other hand, was your play.”
Patrick Wilson - Jeff Kohlver
Ellen Page - Hayley Stark