Volume 2: Miles Behind us
- Hershel finally learning the truth about zombies... After losing two of his children to them.
- Donna's death can be a hard pill to swallow, because we were just starting to warm up to her and, boom, dead.
Volume 3: Safety Behind Bars
- Hershel finding two of his daughters brutally decapitated, and reacts how you would expect a father in that position to react.
Volume 4: The Heart's Desire
- Carol slitting her wrists after breaking up with Tyreese, who was given oral sex by Michonne, and how it leads to Tyreese and Rick fighting and permanently testing their friendship.
This Sorrowful Life
- The sudden death of Doctor Stevens. And his last words to Alice.
Volume 7: The Calm Before
- Carol's suicide after gradually being broken mentally. Everyone watches on in horror as she walks into the zombie's reach, and Sophia's vacant stare afterwards is particularly upsetting.
- Dale feeling insecure and unworthy of Andrea can be kinda depressing.
Volume 8: Made To Suffer
- In general, The Governor's attack on the prison and the casualties suffered. Most notably Hershel desperately dragging a shocked Billy to safety, only for Billy to be shot in the head, leading to Hershel losing the will to live and pleading for the Governor to kill him, which he happily obliges. Similarly, following the Governor's orders, a soldier named Lilly Caul shoots and kills Lori, who falls to the ground and crushes her infant daughter Judith. Unable to cope with what she's done, Lilly murders the Governor in cold blood. The final panel of the volume is Rick and Carl alone, tearfully embracing.
- Tyreese and Axel's deaths are up there as well. The Governor slowly beheads Tyreese using Michonne's katana, and Axel gets shot by an unknown Woodburial in the very next issue not too long after having sex with Patricia. They're actually two of the very few characters that Robert Kirkman misses and regrets killing off.
- Alice's Heroic Sacrifice to save Rick and his family counts too.
- To some, Patricia's death. After trying to make up for her mistakes, she ends up killed in an abrupt way.
- After killing Billy, one of the Governor's soldiers (named in Fall Of The Governor as Smitty) is actually shocked at the fact that he shot a kid dead. He calms down when the Governor reassures him, but this is a huge foreshadowing of Lilly's breakdown and her shooting the Governor dead.
Volume 10: What We Become
- Abraham, Carl, and Rick sitting beside the car talking. From Abraham's story in which several people in the first group he's joined up with raping his wife, daughter and two other girls while making his son watch. When he finds out, he goes on a Roaring Rampage of Revenge which scares his family enough to cause them to leave. He goes after them, and when he finds them, they'd been attacked, with his daughter zombified, forcing him to kill her. Then he joins up with Rosita and Eugene's group, three people try to take some supplies and leave, forcing him to kill them. He then sits crying, wondering if he's become a monster like the zombies around them. Rick then tells how he killed Dexter during the roamer fight, and how he ran over Martinez with the RV before beating him to death. Rick then says that what they're doing is necessary to protect those they care for, and how he worries about what would happen if Carl knew. And if that weren't enough, Carl talks about how he shot Shane in the neck to protect Rick, and how he wished he could kill the man who killed Lori and Judith, as well as help kill the man who tried to rape him. The scene ends with Carl and Rick embracing in tears while Abraham sits silently next to them.
- Morgan saying good-bye to his zombie son, even refusing to properly kill him and instead releasing him from restraints.
Volume 11: Fear The Hunters
- Even though they were cannibals, Chris' group needed to survive. And the look on his face before Rick's group kills them was just heart breaking.
- Dale's death.
Volume 14: No Way Out
- Morgan talking to Carl on his deathbed. Made even worse when he confuses Carl with his son. Guy just can't catch a break.
Volume 17: Something To Fear
- The absolutely brutal death of Glenn at the hands of Negan and his baseball bat as several of the other survivors are Forced to Watch.
Volume 24: Life And Death
- Alpha kills Ezekiel, Rosita (who was pregnant with Eugene's baby) and ten other survivors of the Kingdom, Alexandria and the Hilltop by luring them out into the open by posing as a friend of Rick's. The worst part is that both victims wanted to rebuild their relationships with their lovers before getting decapitated. There heads are latter seen on pikes outside of Alexandria, where Rick's group mercy kills them along with the other victims of the Whisperers.
Volume 28: A Certain Doom
- The death of Andrea. From her zombie bite on her neck happening as a result of saving Eugene (with Eugene later crying and believing that it was his fault) to Carl holding back his tears, to everyone (even Negan, of all people) giving their condolences, to Rick and Andrea's final conversation, to Rick initially wanting to let a zombified Andrea bite him, and finally, Rick tearfully stabbing Zombie!Andrea's head to kill her for good. All in all, this may count as one of the most traumatising, devastating and saddening deaths one can ever read about in the history of The Walking Dead, since Glenn, which says a lot of things. Robert Kirkman wasn't joking when he said from issue 166's Letter Hacks that the next issue containing this certain death would be a "big deal".
Rick: I love you so much.
- It's more saddening when you notice that Andrea became infected by being bitten on the right side of her neck, just like her sister and lover before her, with the latter of the two having enough time to provide thoughtful, heartwrenching advice all while dying by their lover's side, which is what Andrea did.
- The last ever exchange:
(Andrea looks back at Rick, with a smile and tears falling down her face)
Andrea: Yeah, you do.
- Even worse, in the issue that contained her death, there was no monthly Letter Hacks at all, only a eulogy written by Robert Kirkman himself:
I'm sorry to my fans and to myself and to Andrea. I feel like I killed a close friend. The deaths in this series are never taken lightly, they're never done with a sense of glee. They weigh on me the same way they weigh on you. These characters are very real to me, and their deaths are very upsetting even to me.
I plotted this issue out during a plane ride a few months ago. I plot my stories down with a pencil and paper, and there I was in my seat. blocking out scenes and writing dialogue notes, surrounded by strangers who probably thought I was jotting down a shopping list. As I was writing some of the moments in this issue, I started crying. I found myself glancing around, wiping my eyes, hoping no one would notice. I've been living with this death for months now... and I don't like it.
I had plenty of time to change my mind. I had plenty of time to just not do it. I am in control of this story after all. But honestly, sometimes it feels like I'm not. This was one of those times. I don't like this. I don't want this. I want Andrea to live. I want to write more stories with her. I want to see her and Rick grow old together, watching Carl grow up and have kids of his own. I want that kind of happiness for these characters.
And yet, here we are.
Andrea is dead and the story moves on. I don't know why this had to happen... but I know it did. I know this is another important turning point in the life of this series. I know Andrea's death will mean something, that it will resonate the stories moving forward for years to come. But I still don't like it. It still upsets me.
I loved Andrea and I will truly miss her.
- Robert Kirkman
- The ending of this volume makes an even bigger pile on this moment. Despite fending off the Whisperer's zombie herd and beginning cleaning up Alexandria, Rick cannot speak a word, and goes outside to sleep on Andrea's grave. This demonstrates that despite her helpful and inspirational words for him to continue being a leader, her death still happened, and he couldn't stop it.
Volume 29: Lines We Cross
- Aaron and Jesus discover that Beta was a famous NBA player, and lament that he went from riches to surviving in the woods.
- Maggie confronts Negan in a truly gut-wrenching scene. Negan begins outright begging Maggie to kill him, ashamed of killing Glenn and everything else he's done. He comes to a realization that Glenn was Maggie's Lucille, and accepts his death at her hands. At one point, he even grabs her hand with the gun and forces it towards his forehead, highlighting just how desperate and willing he is to let Maggie get his revenge on him."I can't live like this. I can't be alone. I can't... This is what I deserve. Pull the trigger, Maggie. DO IT! PLEASE. Picture Glenn's face. Remember that. Remember that?! Remember what I did? That's who I am! That's what I'm capable of. I could do that again. I want this. Please. I want it all to end. I'm ready for this to be over! I want you to kill me. Will you please just kill me?! Please! Please."
- Maggie coldly, calmly asks if Negan can remember his dead wife and her voice. Negan begins wistfully recalling it... only for Maggie to cut him off and snarl that whenever she tries to remember Glenn's voice, she hears him screaming her name in his garbled dying breaths. And when she tries to remember his face, she sees his eye hanging out of his skull and his head smashed in. All while Negan laughed and smiled. Negan is so shaken that he fully admits that he deserves to die at her hands.
Volume 32: Rest in Peace
- Issues 191 and 192 brought us the biggest moment this side of the prison's fall, Carl losing his right eye, Negan's introduction or the reveal of the Whisperer's brutality: the death of Rick Grimes, former sheriff and leader of Alexandria. His death is a sharp contrast from how Andrea died, in multiple ways:
- Andrea got bit by a walker after she tried to save Eugene from being swarmed by a herd. Despite this injury, she continued with her task of diverting the herd away from Alexandria Eventually, she collapsed, and spent her final hours encouraging Rick and Carl to keep on surviving for the sake of a better future for everyone else. Multiple friends from Alexandria, the Hilltop and the Kingdom also came to her side to share their feelings about her. At night, the last tearful words she spoke were that of agreeing to Rick's Love Confession, and she finally passed away in her own bed soon after. When she reanimated, Rick was there to hesitantly put her down.
- For Rick, it's a completely different story. Issue 191 began with Rick giving an awesome speech during a standoff between his friends and the Commonwealth army. He is successful in resolving the conflict, and everyone goes back to business. The last exchange he has with anyone, before he unintentionally heads towards his fate, is Carl. He teaches him the importance of always standing up for what's right, and to never succumb to loss due to others needing a sense of hope or victory. They stop by at the hotel where Rick is staying, and he leaves, proudly calling Carl his son and wishing him goodnight, with Carl doing the same. These are the last and only good things Rick experiences.
- Later, he is asleep, but Sebastian Milton barges into Rick's bedroom and threatens him with a gun, accusing him of ruining his family's work. A small talk ensues, as all Rick can do was try to talk him down from shooting. Then, one silenced gunshot is unexpectedly fired at Rick's chest, and Rick is as shocked as Sebastian is. This issue's last panel ends with Rick gripping his wound, with Blood from the Mouth and weakly asking what Sebastian did.
- In the next issue, Rick is full of disbelief as ever, as he's bleeding out. As he raises a hand towards Sebastian, the panicked teenager shoots Rick three more times in the chest and hurriedly leaves the room. It is there that Rick dies, with a horrified expression on his face, and lying on a now blood-spattered bed that was provided by the Commonwealth. That shot alone resembles how Rick woke up in his hospital bed from his coma: terrified, and heading into a different, brutal world.
- The next morning, Carl wakes up and is happy at the prospect of treating his father to pancakes. So, he heads towards Rick's room... and lo and behold, Rick is walking around zombified. Quick reflexes causes Carl to pull out his pistol and put his father down for good with a Boom, Headshot!. It is there that a single tear runs down Carl's face as he realises who he shot, causing him to collapse on the floor, unmoving even when everyone else finds out what just happened.
- To conclude, all it took was one entitled brat to end a man who lost so many friends and family, and who fought so hard to create a new, fresh civilisation. Because of those four silenced shots fired, Rick's life was cut short, robbed of any dying heroic acts, noble final words, grateful comments from followers nearby him or even a final gaze at Alexandria, the place where be brought together countless people against walkers or antagonistic humans. For someone who was mighty and could survive anything thrown at him up until this point, Rick Grimes had nothing worthwhile in his quick, last moments. It's even lampshaded in 192's end, where Carl breaks down crying from the feeling that Rick, unlike Andrea, did not get a proper departure, and that Carl will not be able to keep his father's work going.
Rise Of The Governor
The Road To Woodbury
- Josh telling Lilly about the fate of his mother. When he got home from work he found her remains spread out across the table at his house. Apparently, she mistook the zombies for starving homeless people and let them inside herself.
- Josh's death. Its extremely sudden and happens right after he and Lilly have a falling out after she told him that she might not actually love him. What makes it worse is just how senseless it was, he didn't get attacked by a walker or suffer an accident, no. He died because he refused to hand over a bag of supplies he found to the butcher, who was already working him like a dog and driving up his debt to him. The kindest, nicest person to survive the zombie apocalypse and he gets shot in the back of the head out of petty greed. Damn.