In the episode "We Shall Live Forever", Hood and Carrie finally have it out, and he screams at her that its not fair that she denied him his family. He spends most of the conversation near tears.
A smaller one, but its certainly sad to see in flashbacks just how close Hood, Anna, and Olek were. And where they're at now.
Siobhan Kelly's death and the aftermath.
Hood's sobbing really makes the scene: in that moment the badass, snarky ex-con-ex-special-forces-real-cowboy-fake-cop gives way to a hurt, frightened child being served a harsh reminder of just how cruel the world he lives in really is. Which is probably what Hood is, deep down, under all those levels he was forced to take.
Rabbit telling Hood that in a few years time, Hood will be just like him alone, angry, and without the woman he loves. Hurts quite a bit when you think that Hoods main motivations thus far have all be about protecting or just plain getting to know said family.
When Hood is handcuffed and trapped, waiting for Rabbit to come kill him, he seems almost resigned to his fate. Then he sees that Deva is one of the kids being held hostage at the school he completely panics. Doubles as a CMOA as he then manages to rip off a side of the bed to get free.
Siobhan's house being burned down.
Emmett's death. Double painful as it came out of nowhere at the end of the season, just after you think he's finally made it out
The attack and subsequent miscarriage that happens to his wife is pretty damn awful.
Hoods entire back story if you think about it. The guy grew up in An abusive household, joined the military, but had massive problems with authority. Instead of being kicked out, its hinted that he got recruited into some sort of Secret Service/ NSA sect of the government. We don't know how long that lasted but at some point he left the NSA and had Job completely wipe him from the technological face of existence. He then started picking up the odd smalltime crime job, got in with the Ukrainian Mob, fell in love with the Mob boss's daughter, planned to run away with her using the cash from a massive diamond heist, but got screwed over by said Mob boss who then made him rot in jail for 15 years where its implied and explicitly stated that he was routinely beaten and abused both mentally and physically. He gets out of prison, goes to find the woman he loves and finds out that not only has she moved on, but she had his daughter and never even told him. Yikes.
The Banshee Origins short 'Looking For My Exit', which has Carrie sitting in a car, right outside of Hoods prison, 11 years ago, looking heartbroken. When Gordon calls to ask where she is, she says she's just looking for her exit. There is clear double meaning in the words, but its not clear if she thinks of Gordon as her 'exit' from the crime life, or if she is waiting for Hood and thinking of anyway that things could be different.
Made all the worse when you think Hood still thinks that she just completely abandoned him there. She did visit, she just couldn't bring herself to go in.
Carrie and Deva's origins. While its heartwarming to see that Carrie at least didn't lie about Deva not being biologically Gordon's, its awful to see how Carrie reacts to being asked about him, how she just shuts down and won't even discus him with Deva because it hurts to much.
And then her memories off the 'rose-tinted' moments she had with him when he first gave her the locket.
The Truth About Unicorns is actually very sad when you think about it, seeing as its a whole episode revolving around Hood desperately wishing his life had been different, and that it had all worked out for him and Anna (and Deva).
Carrie finding the unicorn and lamenting her damaged relationship with Deva caused by her lies.
Hood killing the sniper sent after them by Rabbit - just moments before he said that enough people had died over the whole fiasco, and the look on his face as he drives the assassin's own knife into her throat is one of pure anguish; but he does it anyway, because otherwise she will just keep coming back.
Carrie tearfully telling Gordon the truth about Hood.
Any time Hood cries.
Banshee Origins: Interrogation when Hood realises that it was Olek that ratted him out. At this point, Olek is still like a brother to him.
The flashbacks of the night Hood got arrested, seeing his goodbye with Anna.
And then the same scenario, and the same goodbye, happening in the big church shootout.
Hood having a complete panic attack at being trapped inside building thats on lockdown with the cops coming. He starts having full on flash backs of prison and only Carrie can pull him out of it.
In the back ground of the aftermath of THAT fight in episode 3, watch Ana/Carries face. Part of it is horror and disgust along with everyone else, but it seems like at least part of her is thinking "What the hell did prison do to you?". The sheer brutality that Hood shows is new to her, something we know he had to learn inside to stave of the constant attacks, but this is the first time that Ana has really seen just what sort of hell he was living in for those 15 years. Her shocked face really does say it all.
Gordon's death. Especially Deva's reaction by coming to the Cadi and just running over to Hood.
While he is a villain, something about his deep calm voice and his drawn facial expressions make you really feel sad for Cheyton. By the time it gets to his death, seeing him so worn down from this imposing godlike man heartbreaking.
Seeing just how badly Hood was affected by the events of Season 3 during the flashbacks in Season 4 is heartbreaking. He was left completely broken, on the verge of suicide (and he might have committed suicide too, if not for Rebecca's help) and ended up isolating himself in a small cabin in the woods for two years, living like a reclusive hermit.
Rebecca's death. She may not have always been the nicest of people but it's still very sad to see how horrifically she was killed. It doesn't help that she's shown in a much more sympathetic light in the flashbacks. Made even worse when it's revealed she was still alive while being gutted and having her heart ripped out. Made even more worse when it's later revealed she was pregnant, with Hood's baby.
It is incredibly sad to see the reunion between Job and Hood, Carrie and Sugar when Job is finally freed after being tortured for two years. It's clear the torture has left a toll on him but he still attempts to be his wise-cracking self.
Surprisingly enough, neo-nazi Calvin Bunker’s death is one of these. Not so much because of him dying, but more because his big brother, and reformed ex-nazi, Kurt is the one who has to kill him. After a brutal fight between the pair where Calvin blames Kurt for ruining his life, and Kurt finally realises he will never be able to save his little brother, Kurt tearfully has to shoot Calvin as he rounds on him again. As Calvin dies, he continues to stumble toward his brother, before finally collapsing in his arms. Kurt then completely bursts into tears, cradling his brothers dead body. Its the culimnation of 2 seasons, or a lifetimes worth of brotherly angst and pain, and your heart really does break for Kurt in that momment. The Musical accompaniment of ‘Roam' by Broken Twin really does not help the situation.
It's much easier to feel sorry for Calvin when you consider it was Kurt who brought him into the Brotherhood in the first place, thus being to some degree complicit in his brother's eventual downfall.
