“- Skylar: Maybe we could go out for coffee sometime?
- Will Hunting: Great, or maybe we could get together and just eat a bunch of caramels.
- Skylar: What?
- Will Hunting: When you think about it, it's just as arbitrary as drinking coffee.”
Minnie Driver - Skylar
Matt Damon - Will Hunting

“Had he been a younger man, he probably would have made it. That's the point. Don't wait too long in life.”

W.C. Fields - Egbert Sousé

“There are a great many chances for advancement. Who knows? Within a short time, you may become my Vice President. My first and only vice.”

Pierre Watkin - Mr. Skinner

“I think the world has been run long enough by well-meaning professionals. We might give the amateurs a chance now.”
Laraine Day - Carol Fisher

- Mrs. Van Hopper: Most girls would give their eyes for the chance to see Monte!
- "Maxim" de Winter: Wouldn't that rather defeat the purpose?
Florence Bates - Mrs. Van Hopper
Laurence Olivier - "Maxim" de Winter