Voiced by: Kirk ThorntonThe main protagonist. After a car crash, he loses his young daughter Cheryl and will stop at nothing to find her, no matter what abominations he must face. Turns out, he has been dead for years and may or may not be a figment of Cheryl's imagination: a "perfect" idea of her father she created due to the guilt she felt for his death.
- Action Survivor: This time, Harry literally cannot fight Silent Hill's monsters and has to run away from them... Yet he manages to survive exploring the entire town with nothing but quick wits, some flares and a flashlight. Justified, as Cheryl really admired her dad, and his part of the game is nothing but a figment of her imagination.
- Alternate Character Interpretation: Invoked: What his character could be said to be built upon, as in game decisions can lead to four different epilogues that portray him in four different ways that just can't match one another.
- Broken Pedestal: To Cheryl in all the endings, to varying degrees. Depending on the player's choices, she can come to see him as just a regular dad instead of a superhero or a jerkass drunk who regularly cheated on Dahlia.
- Dead All Along: A weird case where the protagonist is this.
- Non-Action Guy: Although you are controlling him to hurdle, he actually isn't a hero.
- Papa Wolf: Harry is once again ready to go To Hell and Back to save his little girl.
- Which may or may not be true, considering that he's practically Alternate Character Interpretation incarnate in this game.
Cheryl MasonHarry's young daughter, gone missing after he crashed his car. Harry's goal is to find her, no matter what.She actually never was in the crash, which happened 18 years ago, that killed Harry. The therapy sessions in the game are via her perspective.
- Break the Cutie: Harry's death pretty much broke her, mentally and emotionally. She went from being a sweet little kid to a violent delinquent in her teens.
- It's All My Fault: She blames herself for her parents not getting along with each other well and her father's death. A big part of her healing comes from her recognizing that no, it wasn't her fault. In at least one ending, it wasn't anyone's, it just happened.
- Parental Incest: If her feelings for daddy are interpreted in really screwed up ways.
- Unreliable Narrator: In the sense that Harry's quest is actually in her head. How much of the Harry you play reconciles with the real one is very difficult to be certain of.
Voiced by: Kirsten PotterA cop who flip-flops between helping or hindering Harry, and will act and dress differently depending on how you act in the game and answer the questions in the therapy session.
- Call-Back: Her sexy outfit looks a lot like what Cybil wore in the original Silent Hill.
- Fair Cop / Ms. Fanservice: If you have very sexual views during the psychological test, Cybil will have a very racy appearance and outfit that belongs less on a cop and more on a bar girl.
- Expy: In her Nice Guy persona, she is clearly modeled on Mariska Hargitay.
- Jerk with a Heart of Gold: In her more standoffish persona.
Dahlia Mason (née Gillespie)
Voiced by: Laura BaileyA woman who mysteriously pops up in the game midway, who hits on Harry as if she was his lover, despite Harry having no clue who she is. Her clothes and attitude are affected by in-game choices and the therapy sessions.In reality, she is Harry's ex-wife and Cheryl's mother, who Cheryl resents heavily.
- I Was Quite a Looker: The years of having to be a single mother, not to mention widow, and deal with a rebellious, possibly even delusional, daughter who blames her for everything have not been kind to her. Subverted, as she appears this way because this is how Cheryl sees her. In the "good" ending, Dahlia looks like any other video game conventional mother.
- Misblamed: In-Universe, Cheryl blames her for the divorce and Harry's death, but Kaufman points out she isn't responsible.
Voiced by: Michael McConnohieThe therapist that is seen in the first-person therapy sessions. He is bitter and pessimistic about marriage and love.
- The Alcoholic: Implied, but he smashes his drink out of anger. Although considering that he is viewed through Cheryl's point of view, he might not actually be one.
- Anti-Villain: He really is just trying to cure Cheryl of the obsession which has devastated her life.
- Big Bad: In a way he is this in the game due to him trying to get Cheryl to forget about Harry.
- Brutal Honesty: He does not sugar coat anything. He bluntly tells Cheryl she's been remembering a fantasy and she will never know her father.
- Dr. Jerk: At times bordering on The Gadfly; in a few of his tests, he seems to be deliberately trolling the patient. It's implied that he's doing this in an attempt to draw a troublesome patient out.
- Good Is Not Nice: You may have noticed all the Jerkass tropes listed for him, but he really is a well-meaning person.
- Hidden Heart of Gold: During the ending.
- Jerkass Fašade: His jerk attitude steadily increases over the course of the game, but his final words make it clear that he really does care about his patients and wants them to get better. It's implied that being a jerk to his patients is simply his method since he's something of a last resort when it comes to troublesome patients.
- You Need to Get Laid: "You know, people who are getting enough don't need psychoanalysis. You clearly are not getting enough."
Voiced by Kate HigginsA former student/prom queen of Midwich High School and the sole attendee of the high school reunion (canceled due to the snow storm). She claims that she attended school with Cheryl Mason. She is currently dating a guy, but he either breaks up with her, or vice versa, depending on player actions. Her outfit changes depending on the in-game actions and the answers in the psychological parts of the player.One of the endings implies that Harry was having an affair with Michelle, along with Lisa, behind Dahlia's back.
- Genki Girl: She is easily the most upbeat of the cast.
- No Accounting for Taste: Her relationship with John.
Voiced by: Karen StrassmanA nurse at the hospital in Silent Hill. One of the endings implies that Harry was having an affair with Lisa, along with Michelle, behind Dahlia's back. She dies, though it may or may not be the player's fault, depending on the player's actions.
- Doomed by Canon: Her death cannot be prevented, and is a callback to her death/mutation in the original game.
- The Cutie: Despite her jaded outlook, Lisa easily comes across as this.
- The Cynic: Played with. Despite her cynicism Lisa is always friendly to Harry. Unless the player gives her the wrong pill, that is.
- Too Dumb to Live: If you give her the wrong pill, she'll take it sight unseen. She also downplays the severity of her head injury, and that's what kills her even if you give her the correct pill.