Boyd: You gonna shoot to stop me? Raylan: Maybe. Boyd: Iím pretty sure youíre empty. Raylan: You gonna bet your life on that? Boyd: No, Raylan, Iím gonna bet my life on you being the only friend I have left in this world.
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.
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. This troper can't even do it justice. It must be seen to be truly appreciated.
The second season finale, "Bloody Harlan," when Raylan talks down the enraged and emotionally damaged Loretta despite having been shot only moments earlier. His unwavering devotion to the girl makes this troper want to bawl like a baby.
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.
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. Winnona 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 Magg'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.
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.