“- Young Shakes: You have any friends who aren't in jail?
- Father Bobby: Not as many as I'd like.”
Joe Perrino - Young Shakes
Robert De Niro - Father Bobby

“- Valo: Yo, what was it like though, being in jail for the first time? Was it good?
- Ry: Just drop it.
- Valo: Did you meet any new friends?
- Ry: Just drop it, alright?”
Bam Margera - Valo
Ryan Dunn - Ry

“- Boss Spearman: I believe you have a friend of ours in your jail. His name's Mose Harrison.
- Sheriff Poole: I got him here. He started a fight in the general store.
- Boss Spearman: Mose don't start fights. He just finishes them.”
Robert Duvall - Boss Spearman
James Russo - Sheriff Poole

“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