- The sordid history of Walter Sullivan, which pretty much sealed his fate as, at the very least, a very disturbed individual. The first detail that will likely kick you in the gut? He was abandoned as a newborn baby. Yes, umbilical cord and all. His parents, especially because of the father's reluctance, fled the scene and pretty much left him on the floor in the middle of the enigmatic apartment. Frank Sunderland, the building superintendent (also James Sunderland's father) found Walter for himself. Now, growing up as an orphan can be a traumatizing experience for any child, but Walter somehow got it even worse, as he eventually ended up under the tutelage of the cult that had infested Silent Hill for much of its history. One of the things the cult put him through, as well as other children, was to lock him up in what is, for all intents an purposes, a prison. In that same prison, he and other children were tortured and assaulted by one of the sadistic guards running the place. As time went on, the cult bred within him the desire to undertake a ritual that they misled him to believe would give him his mom back. It was really meant to bring about their god but still, Walter had no chance of being happy and fulfilled, only instead to be a pawn of a cult and to take a nose-dive into darkness and death.
- The death of Cynthia, especially because she thought she was lost in a dream the whole time. Believing Cynthia will forever be chained to Silent Hill as a tragic ghost.
- The ending of Apartment World Part 1. Henry is racing to rescue Eileen from Walter Sullivan but is designed to fail, arriving to see Young Walter standing over a bloody Eileen and apparently thanking him for intervening. After she loses consciousness, Henry falls to his knees in grief and a melancholy piano track plays to highlight his sense of helplessness. Fortunately, she's still alive and you meet her again in the following world, but Henry takes it hard.
- Henry's first meeting with Eileen in the hospital. She just barely survived her encounter with Walter, and waking up to see a man looming over her again frightens her so much that she starts crying hysterically until Henry calms her down. As bad as the eventual Escort Mission ends up playing out, that one moment was certainly enough to make players sympathize with her.
- Despite the fact that he's been trying to kill you throughout half of the game, Walter's death is surprisingly sad. He's lying on the ground, reaching up towards the light at the roof of the dome you've been fighting in, whispering "Mom..." before finally dying. Just to hammer home the fact that all he really wanted was to be with his mother, his younger manifestation, who is still knocking at your apartment door, collapses and disappears. And then the door finally creaks open.
- The "Eileen's Death" ending. Henry, master of Dull Surprise, sounds absolutely heartbroken...
- The worst ending, where Henry fails to cleanse his apartment sufficiently, and Eileen ends up being sacrificed in the final battle. Killing Walter turns out to be a hollow victory, as Henry presumably becomes possessed and dies back in the real world. A view of Henry's "unholy" apartment as it appeared at the beginning of the game is shown as a news report and is broadcasted on the radio, announcing the death of Eileen and the police finding Henry dead in his bedroom, severely disfigured. Getting this ending your first time playing the game, you might end up feeling very depressed and it's fairly likely this will be your first ending. Even adult Walter looks depressed, apparently in despair that he was deceived and the 21 Sacraments did not do what he thought it would do.
- The various cutscenes you can witness in the second apartment level which connect Eileen and Walter. If Eileen hasn't been attacked very much, she'll read Walter's history and sympathize with his plight, seeking to help him out of pity for what he's been through. If she's somewhat injured but not too badly, she can feel his presence in her mind and is absolutely heartbroken by the pain she empathically senses through their growing bond, until she's eventually driven to leave Henry in a trance. Finally, if she's fully possessed, she's plaintively whimpering for her "daddy and mommy", acting as young Walter's voice all while demonic tendrils swirl around her battered body, and she can only be snapped back to her senses for a couple seconds before returning to Walter's crying. It can honestly make you feel like such a dick for allowing her to be hurt that much.
- The ultimate fate of most of Walter's victims, according to notes you find. Granted, several are not very nice people, but none did anything worth being damned to haunt his nightmare world. One can hope that defeating Walter freed them, but even that is... ambiguous.
- Even the best ending "Escape" come across as bitter-sweet. The music is triumphant yet has a hint of sadness like Henry and Eileen will carry scars from being trapped in Walter's Otherworlds. The fate of Walter's victims trapped in his nightmare is left unresolved, as mentioned above.
Tear Jerker / Silent Hill 4