“- Gloria: Why didn't you ever marry?
- The Great Man: I was in love with a beautiful blonde once, dear. She drove me to drink. That's the one thing I'm indebted to her for.”
Gloria Jean - Gloria
W.C. Fields - The Great Man

“Too bad about Wade being burned to death. He owed me a lot of money.”
Kenneth MacDonald - Jake Jackson

“Those days whenever I had half a dollar that didn't belong to the butcher, the landlady or the street car company, I'd go to a concert”

Deanna Durbin - Abigail Martin

“- Lawrence Bourne III: I need to have a talk with you; sort of a little father-son chat.
- Lawrence Bourne Jr: Have we ever done this before?
- Lawrence Bourne III: No, we're breaking new wind. Dad, I need $28,000; it's the matter of a little gambling debt. I can assure you it will never happen again.”
Tom Hanks - Lawrence Bourne III
George Plimpton - Lawrence Bourne Jr.

“- Eddie: You're in debt? What kind of debt?
- Lila: You know, the kind where you owe a lot of money to people.”
Ben Stiller - Eddie
Malin Akerman - Lila