Corruption, violent crime and a cast full of adulterous Jerkasses can't make Bubbles walking up those stairs any less heartwarming.
As a stone-cold killer, Wee-Bey comes across as generally warm and funny. But there's nothing like the moment where Bey agrees to give up Namond to Bunny.
Wee-Bey: Man came down here to say my son can be anything he damn please.
Rawls taking McNulty aside and telling him that getting Kima shot was not his fault, assuring him that, even though he is a "gaping asshole" that nothing that happened was his fault, and if it were, he'd be the one leading the charge for his arrest.
McNulty's tearful apology to Kima.
D'Angelo's final conversation with his mother in Jessup, telling her he intends to carry the weight of the Barkdales, only asking that she as well as Stringer and Avon leave him to serve his sentence in peace.
Bubbles finally coming to terms with the death of Sharrod in a heartfelt speech to his support group.
Bubbles: Ain't no shame in holdin' on to grief, as long as you make room for other things too.
Kima reciting the West Baltimore version of "Goodnight Moon" to her son Elijah
Kima: Goodnight Po-Po
Elijah: Goodnight Po-Po
Kima: Goodnight Fiends
Elijah: Goodnight Fiends
Kima: Goodnight Hustlers
Elijah: Goodnight Hustlers
Kima: Goodnight to everybody
Elijah: Goodnight to everybody
Kima: Goodnight one and all
The cop funerals, except for the last one. When a supporting cast member dies, their character also dies and gets a proper send off from Baltimore's Finest.
Jay Landsman: He was called. He served. He is counted.
Hell, the last one was pretty heartwarming too. Seeing Landsman of all people giving McNulty a heartfelt (and even tearful) send off was sweet to see.
Slim Charles' willingness to take blame for Cutty. Despite the fact that Cutty had a chance to kill Fruit but decides not to Slim instantly says its his fault for attacking too early (which is wrong) despite no evidence to say so. Especially heartwarming as most dealers in the show happy to blame each other
Cutty leaving the game, all of it, combined with Avon's cool reaction about it. When Slim Charles laments Cutty's departure with a mildly disparaging remark, Avon is quick to defend his former soldier: "he a man today, he a man."
Dennis "Cutty" Wise is just starting to get his boxing gym together, but all he has is beat-up old equipment that is falling apart. Knowing he'll never get a loan from a bank, he goes to the only person he knows that can fund the project: Avon Barksdale. Avon sits unimpressed and almost seemingly disinterested while Dennis does his sales pitch, and asks Dennis how much he wants. Obviously expecting rejection, Dennis asks for $10,000. Avon laughs at him for only asking for $10,000, and has Slim Charles go get Dennis $15,000 in cash, no strings attached.
Avon: You take care of those little niggas, you feel me?
When Landsman, the most statistic and career concious cop in Homicide, decides to let Bubbles go, with the words "Fuck the clearance."
If you put the events of Season 5 out of your mind, McNulty having a stable relationship with Beadie and seeming genuinely happy during Season 4 is pretty heartwarming to see.
Waylon's speech to the addicts at Narcotics Anonymous in Season 1. He's a world-weary addict who's been through hell and back, and he refuses to sugarcoat the truth of how badly addiction can screw up one's life. But in spite of it all, he makes it clear that he's there to remind every fellow addict in Baltimore that they're not alone.
Waylon: When I was out on them corners, not a pot to piss in, with everybody who ever knew me or loved me cussing my name, you know what I told myself? I said, "Waylon, you're doing good." I surely did. I thought I was God's own drug addict. I figured that if God hadn't meant for me to get high, he wouldn't have made being high so much like perfect. Now I know I've got one more high left in me, but I doubt very seriously that I have one more recovery. So if there's anybody out there that sees that bottom coming up at them, I'm here to talk sense. I don't care who you are, what you done, or who you done it to. If you're here...so am I.
Waylon's unexpected reappearance in the Season 4 finale, when he shows up to comfort Bubbles in the detox ward of the downtown hospital following Sherrod's accidental death, and Bubbles' subsequent suicide attempt. We never find out what he says to Bubbles—we just see him cradling him in his arms from a distance as he breaks down into uncontrollable sobs. As much of a Tearjerker as that episode is, it reminds us that Waylon kept his promise: he showed up without any warning or explanation, just when a fellow addict needed him most.
McNulty deciding to not sleep with Beadie after seeing a picture of her kids, knowing he'd only screw up the good life she has. He only approaches her about getting together when he's in a far better place himself.
Wee-Bay and Chris bonding in jail during the ending montage of season 5.
Bodie and McNulty earning one another's mutual respect in the Season 4 finale, right before Bodie is killed in a corner shootout.
Snoop giving a store clerk 800 dollars, telling him to ring her up and keep the rest for himself, saying that he "earns that shit like motherfucker". Doubles as a Crowning Momentof Funny.