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 goes to Father Ray and asks if he thinks that God is punishing his son because Alvarez had bragged about him too much. Ouch.
The execution of Donald Groves.
Rebadow crying in his cell after he admits to Mc Manus that he's too ashamed to tell his grandchild he's in jail. And when Mc Manus 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 final rejection of Keller.
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'Reilly 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.
Opinion divided on that one, bro. He was too far gone for my taste.
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.
Keller confessing to a murder, so Beecher would not face the charges.
Shirley Bellinger's execution. Child murderer yes, but christ that was potent.
Seconded. She was one crazy bitch but that was some magnificent acting from beginning to end.
Clayton Hughes' 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..."
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.
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.