“I had better sex in prison.”
Ben Affleck - Rudy Duncan

“- Peter: The worst they would ever do is they would put you for a couple of months into a white-collar, minimum-securityresort! Shit, we should be so lucky! Do you know, they have conjugal visits there?
- Samir: Really?
- Peter: Yes.
- Michael Bolton: Shit. I'm a free man and I haven't had a conjugal visit in six months.”

Ron Livingston - Peter
Ajay Naidu - Samir
David Herman - Michael Bolton

“Dude, it's not big deal if you like to fuck guys. I'm cool, I got friends who fuck guys… in jail.”
Romany Malco - Jay

“I'd cut my own throat before I'd let you bring me into custody. Because, number one, I'm a cop. You know what happens to cops in jail? Not pretty. And number two, you're the last person I'd let collect the money. Because you're a goddamn lunatic who ran me over because I didn't call after I nailed you.”

Jason O'Mara - Joe Morelli

“Juan Castillo... went to jail... for having sex with a goat. Ok? We lived on a farm! And I got lonely! We were just a couple of crazykids!”
Steve Lemme - Juan