Dr. Gloria Nathan: You may have breast cancer.
O'Reily: (laughs) That's funny.
Dr. Gloria Nathan: I'm not joking.
O'Reily: Breast cancer? Girls get breast cancer.
Dr. Gloria Nathan: Men do too. It's rare, especially at your age, but it does happen.
O'Reily: I'm not a fag, you know. I've been in this shithole for over a year, and I ain't ever taken it up the ass!
Dr. Gloria Nathan: No one is saying that you have!
O'Reily: Bullshit! You're telling me I've got a chick's disease!
Dr. Gloria Nathan: Men have breasts, the same as women.
O'Reily: What the fuck you talking about? I ain't got breasts, I got a chest! (pulls open his shirt) See it? Huh, see it?!

Hill: Everybody wants to escape from Oz. But the truth is, there is no escape. Let's say you manage to sneak out. Then you gotta run and keep running. A life of running away ain't no life at all. Better to deal with where you live. The real measure of a man is not where he lives, but how; how he makes the best of it.
Season Three

Hill: Evil is the only thing that has survived intact these past thousand years.

Hill: Families! Our families determine who we are, determine what we're not. How we relate to other people is based on the way we relate to the members of our families. No wonder the world's so fucked up.

Hill: Hey Schillinger.
Schillinger: What do you want?
Hill: How much would it cost to mail me out of here?
Schillinger: Mail you? What are you talking about?
Hill: I've been trying to think of ways to get out of here.
Schillinger: Escape from Oz?
Hill: Yeah. And I figured, you know, you could box me up in a crate and mail me to my wife overnight express, Priority Mail, whatever. How much would that cost? Postage, shipping, handling, et cetera?
Schillinger: Are you serious?
Hill: Yeah.
Schillinger: Then you're nuts.
Hill: Is that a no?
Schillinger: Yeah. No. No, yeah, it's a no. Get the fuck out of here before I tip you over.
Hill: All right, Vern, I ain't mad at you. You can't help it if you're ugly and stupid.

Hill: I know what you're thinking. "Boy Meets Girl", that's one boring fucking story. It always goes the same way. But there are variations on the theme, like "Boy meets dog, boy loses dog, boy buys new dog" or "girl meets psychiatrist, girl goes to therapy for the next ten years", or in Oz there's always "boy meets boy".

Judge Grace Lema:I can't tell if I gave You a fair Trial or not.And now seeing You like this,I think maybe the punishment exceeded the crime.And I'm...
Beecher:You're what? Sorry? Your honor, you used all your power to crush Me. But the truth is I did kill Kathy Rockwell, and as much as I tried to manipulate the system to get off, I took her life. According to the law, each crime is worth a certain number of Years. You gave me a maximum of fifteen years in this fuckhole. Is that too much? Too harsh? Not Enough? I don't know. You say you're wanted by what you did? Well so am I. If you came here for me to forgive you, you came to the wrong man. He ceased to exist the same day Kathy Rockwell did. You're not get anymore peace out of him than I do out of her.

Keller: Don't worry. Sooner or later, Beecher'll be mine.

Keller: The way I see it, you and me, we're not like the rest of them. The Muslims, the Homeboys, the Aryans. See, they all got each other. But you and me are sitting out there with our dicks swinging in the wind. We gotta be able to rely on each other. You know, trust each other.
Beecher: It's hard for me to trust people.
Keller: Me too. But we got a long fucking time together, so why don't we see what happens?

McManus: Who told you?
Case: That Ross was the one that shot you?
McManus: Yeah.
Case: You just did.

O'Reily: I can't figure out why the fuck you care, but I'm glad you do. No one's ever given a shit about me my whole life, so I'm not very good at saying thanks.

O'Reily: Would you fucking relax?
Shannen: Don't get pissy with me! I'm the one who's thinking of you!

Officer Metzger: Listen up and listen good: some friends of mine are very upset that you tried to pin a certain murder on them. For that, you're a dead man.
Richie: Oh, Christ!
Officer Metzger: However, they are offering you an alternative: since you're already in here for one killing, they suggest you also confess to Alexander Vogel's murder. Take your chances with the courts. At best, you get life. At worst, you get the Death Penalty. If you get life, my friends will let you live. If not, you're dead anyway. So choose.
Richie: Tell Glynn I need to see him. I have a confession to make.
Officer Metzger: Good boy.

Rebadow: In all my years at Oz, I've learned one rule: accept the hand you're dealt.

Said: Beecher, don't do this.
Beecher: Do what?
Said: Drink.
Beecher: You like to dabble in peoples' lives, huh? Because you're so much better than us, because you've seen the light. You've seen the face of God. So you wave your dick around trying to help us lowly mortals. Hill, Mershah, Groves, Jefferson Keane. Fuck, you helped Jefferson Keane right into a lethal injection. So in the end, when all is said and done, who have you really fucking helped? Other than yourself?
Said: (proudly) Poet.
Beecher: Poet? I just saw on the news, he killed a man. He's coming back to Oz.