“I remember, I was more afraid of my little daughter than I ever was of being in prison.”
Sean Penn - Jimmy Markum

“Benjamin! You nasty youth, your crime has shocked me to the core. Never in my whole career have I encountered this before. Guards! Seize him! Lock him in a cell. Throw the keys into the Nile as well.”
Donny Osmond - Joseph

“We get caught laundering money, we're not going to white-collar resortprison. No, no, no. We're going to federal pound me in the ass prison.”
David Herman - Michael Bolton

“- Raphelson: You won't get away with this. I have friends, powerful friends!
- President Sawyer: And I'll make sure every single one of them joins you in prison!”
Richard Jenkins - Raphelson
Jamie Foxx - President Sawyer

“- Clifford Franklin: Coach, ain't that stuff illegal?
- Jimmy McGinty: What are they going to do? Put you in football jail?”

Orlando Jones - Clifford Franklin
Gene Hackman - Jimmy McGinty