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    Season 1 
  • The scene where Raylan defuses a hostage situation with some fried chicken and good ol' Kentucky hospitality.
  • This exchange from 1x13, "Bulletville":
    Boyd: You gonna shoot to stop me?
    Raylan: Maybe.
    Boyd: I’m pretty sure you’re empty.
    Raylan: You gonna bet your life on that?
    Boyd: No, Raylan, I’m gonna bet my life on you being the only friend I have left in this world.
  • Boyd not hitting Johnny back when Bo forces them to fight.

    Season 2 
  • Practically every moment between Raylan and Loretta. First, when he gives her his card and tells her that no matter what happens, if she calls him, he will drop everything and come to her side. Second, when he actually does this the night Coover decides to show her where her dead father was dumped and comforts her after the brutal shootout. Third, when she calls him again feeling unsure about the new foster family and he reassures her. Raylan is shaping up to be an amazing Parental Substitute in Season 2.
    • Even after Loretta begins to slide into criminal behavior in the later seasons she and Rylan remain close, and she retains some of the ethics being imparted.
  • Mags desire to provide for her grandchildren throughout the season.
  • The end scene of "The Life Inside" when after all the horrible events with the pregnant fugitive, Raylan rests his hand on Winona's stomach and says nothing.
  • The second season finale, "Bloody Harlan"
    • When Raylan talks down the enraged and emotionally damaged Loretta despite having been shot only moments earlier.
    • Also, the scene when Winona reveals she's pregnant. Raylan is so happy he's speechless. Aw.
    • Maybe it's just me, but the Big Damn Heroes moment when Art, Tim and the SWAT team took out Doyle and saved Raylan doubled as a Crowning Moment of Heartwarming AND a Crowning Moment of Awesome.

    Season 3 
  • In season 3 Raylan and Winnona are making a real effort to make their relationship work. Raylan wants to buy a house so they have more room for the baby. Winona in turn is more understanding about Raylan's work. They look very much in love. Then it turns out she was leading him on for weeks, constantly leaving to live with her sister, but didn't have the gut to tell him. Art, Rachel and Tim knew.
  • In the Season 3 Finale... Arlo taking the fall for Devil's murder to save Boyd from going to prison. It's nice to know he actually cares about somebody.
    • The moment is instantly ruined when you realize he quite possibly tried to kill his own son to protect Boyd, despite the fact that Raylan's only crime is being related to him.
  • Raylan could have dragged Loretta into interrogation and a long, exhausting legal battle to find out if she knew where Mag's money was, but he instead decided to be strict and upfront with her about it, ultimately letting her off the hook. Winona may have ruined his chances to be a good father, but he still manages to be a great Parental Substitute.
  • Sammy Tonin getting a horse for his daughter, whose getting into Black Beauty.

    Season 4 
  • Raylan giving Constable Bob genuine praise at the end of the season 4 premiere. Bob is beating himself for screwing up but Raylan points out that while it was not pretty, when it counted the most Bob stepped up and his actions saved their lives. Bob's face lights up at this since Raylan's opinion means a lot to him.
  • Boyd Crowder proposing to Ava and Ava accepting the proposal. It's very sweet.
  • Somewhat twistedly, Wynn Duffy giving Raylan his condolences for the death of Arlo Givens. He seems disturbed and Raylan actualy thanks him and says that he's probably completely honest. It's a very weird moment. Double points with Duffy offering to take care of the killer as a part of his condolences.
  • When we find out the real story behind Hunter Mosby's relationship with Drew Thompson it starts making sense why Mosby is willing to go to such great lengths to protect Drew. They are True Companions and will go to extreme lengths to protect each other. Then Drew decides that he is not gonna let his best friend sacrifice himself and willingly exposes himself and goes on the run. With Drew's identity no longer a secret, Mosby is no longer in danger from the Detroit Mob.
  • The scenes between Shelby and Ellen May. At first it seems that he helped her mainly because he thought she knew something that he could use against Boyd. However, we later see that he really cares about her and is willing to sacrifice his own freedom and/or life to help her. In return she recognizes what he is doing for her and finally stands up to Ava when she realizes that Shelby is being delivered to his death.
    • In "Peace of Mind", Ellen May hugs Shelby/Drew when she sees that he is safely in marshal custody. Ellen May is overjoyed that her friend is still alive, and Shelby/Drew is comforted by her hug.
  • Cassie St. Cyr keeping Ava from shooting Ellen May. This coming from the person who says she was never the good one in her family.

    Season 5 
  • In "Weight", Dewey visits Dickie in prison. The two friends radiate joy and warmth when they see each other again. It says volumes about the actors' skill when they can make the reunion of a murderous drug dealer and a Neo-Nazi pimp a heartwarming scene.
    • The same episode has Danny Crowe bringing a wreath and flowers to the grave of his dead dog, Chelsea. Later in the same scene, Raylan tells Danny that if he surrenders, he'll let Wendy and Kendal go. Danny actually seems to consider it, before finding out that Daryl is not included in the deal.
  • Wynn Duffy taking care of Mike after Daryl beats him to a pulp, confirming that he does value his bodyguard for more than just protection.
  • Raylan in "Restitution" getting through to Kendal by empathising with him.
  • Alex Miller and Hotrod sharing nips from Miller's flask and reminiscing over their shared history as Hotrod bleeds to death.
  • Wendy and Kendall’s ultimate reconciliation.

    Season 6 
  • Dewey finding his prized turtle dog charm and taking it as a sign to go back to Boyd and apologize. It ends badly, but it's still a good Throw the Dog a Bone moment.
  • Dewey's encounter with his former favorite prostitute Mina, who is working as a waitress since Audrey's closed down, is using her real name instead of the one she used for her fake sexualized sister act, has a boyfriend and seems to enjoy her job. She is polite to Dewey and also shows concern for how Dewey is doing despite their rocky last meeting.
    Mina/Abigail: When Audrey's closed down, put me at the crossroads. I didn't know which way to go. The next day, God sent me a sign..."Now hiring."
  • Markham giving Boyd 10 million dollars to ransom Katherine. Mind you, he already knows by then that Hale is not to be trusted, but it doesn't matter to him.
  • While more of an awesome moment, seeing Loretta offer to let the farmers she’s buying out stay, showing more consideration for the people her actions will effect than most of her contemporaries did.
  • Mike protecting Duffy when Katherine tries to execute him. Mind you, it was Mike who gave Duffy to Hale, being disgusted with his boss being a rat. However, the "protect your partner" part of Mike's "code" was more important than "snitches get stitches." Duffy, for his part crying out in distress after Mike gets shot and comforting him as he's dying. He really did care, even if he didn't show it often enough.
  • When Ava tells Markham that his money is with Zachariah, she lies that he wasn't involved in stealing it in an effort to keep Markham from killing Zachariah. Markham plans to kill him despite that claim, and Zachariah is already dead in a Heroic Suicide, but it's a nice effort.
  • The entire series finale.
    • Raylan and Winona might not be together, but they're Amicable Exes.
    • The goodbyes from Art, Tim and Rachel aren't overly sentimental, but they make it clear with very few words how much they care for Raylan.
    • Raylan deciding not to take Ava in when he sees her son.
    • Ava's son also provides some other heartwarming moments. She shows more concern for what will happen to him than to herself when she thinks Raylan is taking her in. She named him after Zachariah, whom she describes as "he only man in my life who never wanted anything from me." Finally, his very existence allows some part of Boyd to get a better, happier life after Boyd himself crossed the Moral Event Horizon and ended up in prison, implicitly for the rest of his life.
  • While it's more of an Awesome moment, the fact that Loretta's last scene in the series is saving Rylan's life.
  • Raylan and Boyd's final conversation between a two-way glass. After finding Ava, Raylan goes to tell Boyd that she was dead. After a little bit of increasingly awkward banter, Boyd asks Raylan why he felt the need to make the long drive to tell Boyd in person. Raylan tells Boyd that if he allows himself to be sentimental, there's one reason he keeps coming back to:
    Boyd: We dug coal together.
    Raylan: That's right.
  • And two tributes to the late Elmore Leonard in the finale:
    • The book Raylan gives to Tim as a parting gift is The Friends of Eddie Coyle - Leonard considered it the best crime novel ever written and reading it inspired him to stop writing westerns and try the crime genre.
    • Leonard was famously very specific about Raylan's hat - he said that the show was the closest to what it should be, but it still wasn't there. The hat Raylan takes from Boon is much closer to his intention.

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