As a Moments subpage, all spoilers are unmarked as per policy. You Have Been Warned.
- Alvarez losing his baby. And later, during an LSD trip, hallucinating that he's holding his son in his arms and babbling about how he loves him and is going to protect him.
- And, even before that, the moment when he goes to Father Ray and asks if he thinks that God is punishing his son because Alvarez had bragged about him too much. Ouch.
- In the season 5 opener, the prisoners learn from Warden Glynn that their family members (spouses, mothers, etc.) were killed in a horrific bus accident on the way to visit them at Oz.
- It hurts to see Augustus, Enrique, Arif and even Schillinger break down in shock over the deaths of their loved ones.
- The moment when Jefferson Keane, working towards redemption, realizes he accidentally killed one of the two men who attacked him, letting out a bone-chilling Big "NO!" of abject despair.
- Even Adebisi gets a few:
- When he hallucinates a Nigerian dancing ritual in Em City, he breaks down upon immediately realizing that he'll never be able to go home to Nigeria again.
- Jara's death and his reaction to it. Adebisi had been showing signs of making a Heel–Faith Turn after Raja helped him remember his roots in Nigeria, only for Raja to be stabbed by Wangler and Poet, leaving Adebisi to lose the closest thing he had to a father in Oz.
- The execution of Donald Groves - despite having eaten his own parents, Groves himself was a fairly affable guy who clearly didn't belong in Oz, much less deserve the death penalty.
- The death of Leroy Tidd/Salah Udeen. Initially having converted to Islam for the purpose of extracting revenge on Said for killing Adebisi (in self-defense), his conversion becomes genuine as both him and Said bring out the best in each other - Udeen shaking his vengeful motivations while Said begins to move past his guilt over Adebisi's death, with Said even admitting that he knew Udeen was lying at first, but accepted him anyways. Yet when Udeen decides to go back on the deal he made with Robson and Hoyt to whack Said, Robson instead gets a new prisoner in Oz to try and shank Said, only for Udeen to jump in front of Said and get killed instead. As a result, Said's guilt worsens and he blames himself for Udeen's death.
- Rebadow crying in his cell after he admits to McManus that he's too ashamed to tell his grandchild he's in jail. And when McManus tells him his grandson has died, both his reaction and the monologue he delivers is absolutely heart-breaking.
- Beecher screaming in his pod after receiving his son's chopped-off hand by mail.
- Just look at the faces of the other prisoners while he screams and you can tell how bad it is. Said can't concentrate on his prayers, Keller is disturbed by the fact that the man he loves is so broken, and Morales just stares in sympathy. Even Jerkass guard Mineo looks, but then walks away because he can't handle it anymore.
- Peter Schibetta crumbling in despair in a hallway after being intimidated by the warden and taunted by Schillinger again about the several rapes.
- Hamid Khan's death. He was an honest man, who was only in prison for stopping a rape and now that he's brain dead his wife is pulling the plug.
- Perhaps even more heartbreaking is Cyril's reaction to what happened to him. Seeing him slowly comprehend what he did to him and then completely Freak Out was jaw-dropping.
- The moments before Cyril's execution, especially how Ryan sings to him and cuddles him. Also, when Cyril realises what's happening and starts to yell and beg for Ryan.
- Keller's death and Beecher's reaction to it. As well as Beecher's final rejection of Keller.
- Although Beecher's rejection was Keller's own fault.
- Mrs. Smith telling Groves that she does not hate him for killing her son and that she loves and forgives him.
- Beecher forced to confront the mother of the girl that he killed.
- Schillinger telling Beecher that he will not seek revenge for his son's death.
- The inmates learning that their family members died in a bus crash.
- Seamus O'Reily asking to see Cyril, only to be told that he has been executed. Also when he tells Ryan that he's sorry for messing him up and how he never got a break.
- While it's up to the viewer if he deserves any sympathy him telling his son that he doesn't want to die alone, while on the verge of breaking down, does paint a picture that Seamus isn't completely soulless after all.
- Arguably Robson in Season 6. He ends up being a prag, gets raped multiple times, and has a metal spoon shoved up his ass. He deserved most of it, but you can't help but feel sorry for the guy, given that he's one of the few inmates who truly realized how much of an asshole he was and broke down crying in front of Sister Pete, not to mention he actually became much nicer as the season progressed.
- You can see in his sessions with Sister Pete one of the reasons he was so messed up: he was repeatedly beaten, threatened, and raped by his own father.
- Keller confessing to a murder, so Beecher would not face the charges.
- Shirley Bellinger's execution. She killed her own daughter and was so nonchalant about it all the way up to the gallows. As soon as she sees them, her survival instinct kicks in, and she's trying to run away, begging and pleading not to be executed. As she prays for mercy, we are reminded that whether she deserves it or, this is a human being about to be killed. The overwhelming sadness of the likes of Mukada and Sister Pete become, followed by the snap of the noose is the final touch to this utterly bone-chilling scene.
- Seconded. She was one crazy bitch but that was some magnificent acting from beginning to end.
- Clayton Hughes's death. Sure, he may have been annoying at first, but as he lies on the floor bleeding to death, he begs the warden to hug him the same way he did the night Hughes' father was killed.
- "I can feel my legs..." Following that, the closing shot of the episode isn't Narrator!Augustus Hill but his empty chair, making it clear he's really dead. Made even worse in that Hill was one of the very few characters not to do anything horrible in Oz (and maybe the only notable inmate), and he had actually put himself at risk to do the right thing a few times.
- Both instances of all the inmates in Em City banging the glass of their pods for Cyril O'Reily as he was about to be executed.
- In the case of the first, Cyril's last-minute stay of execution verdict, which brings Ryan to his knees thanking God.
- Ryan holding a lock of Cyril's hair as he's being prepared for the electric chair while trying and failing not to cry.
- His lie as to why he's crying also lumped a few throats. He claimed he was sick and crying was the only way to get better.
- The worst part has to be Cyril panicking in the death chamber as he finally seems to realize what's going on and calls out for his brother.
- Keller's moment in Sister Pete's office when he reveals that he abuses the people he loved because he is fully aware of just how horrible a person he is and he wants someone who will love him no matter how bad he gets. Possibly Christopher Meloni's best acting on the series.
- Rebadow calling out for Busmalis as he's being wheeled away to surgery, especially since the two had been feuding up to this point.
- Guerra reflecting how much he's come to hate his criminal lifestyle and his antagonism for Alvarez with Enrique Morales. Morales himself also lampshades how Being Evil Sucks but continued to indulge in it after his sister died in the bus accident because of how horrible a place like Oz is and how its horrible influence has such a hold on his life.
- O'Reily sobbing in Father Meehan's arms when Meehan confronts him about the death of his younger sister.
- Beecher realizing the full extent of his actions upon finding Guenzel naked, bloody, and traumatized in the aftermath of his first rape by the Aryans.
