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- Oddly, the death of Joe the hitman. he faces death with such dignity and sad acceptance that it's hard not to pity him.
- The death of Roland Pike, an immensely likable man trying to turn his life around and ultimately failed.
- Hunter Mosley's agonized monologue about the horrible fate of his niece.
- Gary's palpable desperation and the way his face lights up as he talks about his dream, a dream that will never happen. William Ragsdale turns in a fantastic performance as a man whose ambitions are crumbling before him because he's simply not savvy, smart or tough enough to succeed.
- Boyd's despair and loss of faith when he discovers that Bo has murdered his entire flock.
- The agonizing, horrific death of Walt Mc Cready, a man who was already in despair over the loss of his wife. Even worse, the pain on his face is so clear as Mags tells him she'll take care of his daughter!
- During "Brother's Keeper," Loretta insisting to Raylan that she has a father around to scare off unwanted suitors left this troper a little teary - seeing as Raylan and the audience already know that he's not.
- Mags Bennet may be a wicked, wicked woman, but the look on her face when Raylan tells her she can't see Loretta is heartbreaking
- "Reckoning" gets two to more or less bookend the episode:
Raylan: Don't talk about her like you knew her. You didn't know shit about her. That woman saved my life. Did you know that? Criminal for a father, working a deep mine, wondering what on earth could come along and save me? Helen did. She told me to leave this place behind, be better than Arlo, and she gave me the money to do it. That woman raised her dead sister's kid like he was her own because...[Heel Realization] God damn you, Dickie.
- The beginning of, when Raylan walks into the house where Aunt Helen's body lay, and;
- Towards the end, with Raylan about to execute Dickie, explaining exactly what his Aunt Helen meant to him, and because of everything he remembered she did for her, finds himself unable to kill him.
- Raylan talking Loretta out of shooting Mags in revenge for killing her father by telling her how much it will change her in the season two finale, and in particular:
Raylan: Ask yourself what your daddy would want you to do.Loretta: [starting to cry] I want him to be here to tell me.
- When Mags commits suicide, partially because she seems to be intentionally mirroring her actions from the scene in the first episode of the second season where she poisoned Loretta's father, arguably the most villainous thing she did all season.
- Winona in "When the Guns Come Out" giving Raylan the shaft again, this time probably for real. It's especially painful because Raylan seriously began to think about retirement for her and it turned out she was lying through her teeth about being okay with his job. It was going on for weeks. Art, Tim and Rachel knew. Raylan didn't.
- Ellen May, visibly traumatized after Trixie's death in "When the Guns Come Out," and after Krystal's death in "Loose Ends." Delroy's indirect role in the women's deaths, combined with his callousness to Ellen May's suffering, made it even more heartbreaking.
- Watching Mrs. Dodd after she finds out that her son Tanner is dead.
- In "Guy Walks Into a Bar," listening to Quarles tell Donovan about the sexual abuse he endured as a child. Subverted when we later see Donovan bound in Quarles' bathroom.
- That truly awful moment in the season 3 finale when Quarles tricks the boys' mother into getting out of the van and makes them drive off without her. The heartbreaking moment is seeing her run after the van in vain, tripping and falling, crying for her sons.
- To that end, Raylan's tranquil fury at the death of a fellow cop, especially after he finds out Arlo shot him, possibly because he thought the cop in the hat was Raylan. His face as the episode closes says it all.
- Arlo's death isn't necessarily sad considering what an opportunistic, craven bastard he was, but the impact on Raylan is affecting. Even on his deathbed, Arlo withholds affection from his only son.
- Raylan telling Hunter that Arlo reconciled with him and told him he loved him on his deathbed. Hunter knows it's a lie and Raylan is hardly making any effort to conceal that fact.
- Boyd, after Ava is arrested breaking into the beautiful suburban house he and Ava were going to buy, just to look out at the backyard from the porch.
- In "Over the Mountain", when Raylan takes Kendal into protective custody. Daryl and Danny are horrified, then angry that Raylan wants to take their little brother away. Kendal reluctantly leaves with Raylan to save his brothers, who were about to enter a deadly fight with Raylan to protect the boy.
- The death of Hot-Rod Dunham, of all people, who dies while his Friendly Enemy, Alex Miller, looks on sadly.
- Say what you will about Danny Crowe, but the scene where he brings a wreath and flowers to his dead dog's grave, and tells Raylan about how he saved said dog from a puppy mill is pretty sad.
- Seeing Wendy in "The Toll". She's heavily beaten up, her hair is even messier and after Kendal takes the fall for Daryl, she is practically catatonic and sobbing in a pathetic way.
- YMMV even more than usual, but Daryl's rant to Wendy in "Restitution" where he criticizes her poor parenting skills and lack of involvement with the family, calling her out on the fact that she's the one who handed Kendal over to Daryl, knowing full well what her brother was like. It's a stark look at family dysfunction, and when Wendy demands to know why Daryl thought she wouldn't understand, his agonized response says it all: "You don't want to know, Wendy. You don't ever want to know."
- Wendy and Kendal realizing that while Wendy has been a pretty shitty mother to him, by comparison to the rest of the Crowe family she was doing alright
- The same episode has Jimmy's death and Boyd's reaction to it.
- The Of Mice and Men-esque death of Dewey Crowe in "Fate's Right Hand". Dewey, tired of being everyone's doormat, tells Boyd how he longs for the carefree days of Crowder's Commandos. Boyd points Dewey to a photograph of his ancestors, telling Dewey about their hopes for the future. Boyd shoots Dewey in the back of the head, allowing Dewey to go out quick while hoping for a bright future.
- The death of Mundo (also known as "Choo-Choo") in "Alive Day". After finally finding a person who was not quick to judge him for his appearance and speaking disability, he finds out that his friends are about to betray him and he gets shot by Tim during a stand-off. He ends up parking his car onto the train tracks so that he can be killed by an oncoming locomotive. However, the train ends up stopping just before the impact, and he simply expires from blood loss.
- In "The Hunt", Ava's description of the domestic abuse she endured at Bowman's hands gives viewers a window into the hell she endured as his wife.
- Mike deciding he is loyal to Wynn after all and dying to save him from Katherine. In his final moments as he bleeds to death, he cries out for Wynn to hold him. A distraught Wynn does just that.
- Earl's delayed reaction to Carl's sad, pointless death.
- Markham's reaction to Katherine's death shows that he really did love her, in spite of everything.
- Markham speaking to Katherine's corpse. He's utterly distraught.
- The pointless death of Hagan, a good man in the wrong place at the wrong time.
- Four words: "We dug coal together."