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Harry Mason
Harry's a 32 year old writer who lost his wife a couple years ago to a disease. Harry and his wife found Cheryl abandoned at the side of the road 7 years ago and decided to adopt her. He never did tell Cheryl that she was adopted, and it's been haunting him ever since he slipped into this nightmare.
Cheryl Mason
This 7-year-old has gone through quite a lot in the past few years. Losing her mother was a defastating experience for her and wanted a quiet vacation with her father. Unfortunately, fate had something else in mind and threw Cheryl into a gruesome and horrifying nightmare. Harry never got the chance to tell her she was adopted. Could Cheryl's real parents be behind all these bizzare events? Is this some kind of sick revenge to get back at Harry for depriving them of their daughter for 7 years? Actually, if you defeat Silent Hill, you find out that Dahlia is in fact Cheryl's birth mom. Creepy.
Cybil Bennett
Cybil is the police officer from Brahms, a town near Silent Hill. We first see Cybil on her motorcycle speeding towards Silent Hill. Then, oddly enough, we see a motorcycle crashed at the side of the road. This is Cybil's motorcycle. How she crashed, I don't know. She doesn't even mention it in the cafe. But my logic is that she crashed just the way Harry did. A figure steps out onto the middle of the road, she swerves, most likely misses the girl, but since she's going so fast, she still crashes. Then somehow makes her way to Silent Hill. It's a good thing she did too, because without her, Harry wouldn't have a gun. An essential item for getting around Silent Hill. She also gives him information on the whereabouts of his daughter, and reassures you that your not completely alone in this creepy town.
Alessa
One of the most frequently asked question about Silent Hill is, who's Alessa and what has she got to do with Cheryl? This question is best answered if you go to this website:
Silent Hill Plot Guide
It gives a thorough explanation of the entire plot of Silent Hill. I will tell you some things about Alessa, but it's honestly best to go to that site! First off, Alessa is Cheryl! Dahlia clearly states this at the end of the game. Harry has been running into Cheryl throught the entire game. And the reason Cheryl never talked to him was because Cheryl and Alessa are both conjurations of Dahlia's cult. And yes, I know that Cheryl talked to Harry in the school on the phone, but that was because Dahlia wanted Harry to continue his search for Cheryl. Anyways, the cult wanted to bring there lord Samael to the mortal world, so that he could rule the universe. But for the cult to benefit from all this, they would need to be able to control Samael. The only way to do this was to summon Samael into an unborn fetus, a child that the cult could raise and teach to control it's powers. Dahlia conceived the child with the help of Kauffman (gross!) But when the child was born, only half of Samael's dark soul had been summoned into the child. This child is Alessa. So Dahlia conceives another child (Cheryl) and it contained the second half of the dark soul. This is why Cheryl goes missing in the first place. How she escaped Dahlia and the cult is still a little unclear. Most likely Lisa, not wanting this child to suffer the same fate as the other, stole her and abandoned her at the side of the road, where Harry and his wife found Cheryl. Now this may seem a little unclear to you, but that's because I only explained parts of the story. The whole story is explained in the website that I mentioned earlier.
Dahlia Gillespie
This crazy old woman is always muttering something about the darkness and Samael. She does offer Harry useful items and advice, but her acts are suspicious. She's definitely the creepiest character in Silent Hill, and one of the most important. She cares only about Samael and will stop at nothing to get him into this world.
Michael Kauffman
The doctor doesn't come across friendly to Harry even after he saves the doctor's life. He gets knocked out and awakens to find Silent Hill swarming with monsters and covered in mist. He claims he knows nothing of the bizzare happenings. Though he doesn't seem nearly as upset and shocked as Lisa was when Harry first found her. Kauffman offers Harry no help in finding his daughter, instead he worrys Harry even more! He catches on though to realizing that Harry is talking about the cult's long lost child. So he tells Harry that the chances of a little girl survivng out there with those monsters are slim, hoping that this will discourage Harry from his search for his daughter. He then leaves Harry alone in the hospital without helping him at all.
Lisa Garland
Lisa is perhaps the most tragic character of Silent Hill. She is really nice to Harry when he meets her in the Dark Silent Hill Hospital. She offers him help, and is concerned about his safety. The only time Harry ever meets Lisa is in the Dark version of Silent Hill. These scenes with Lisa happen almost as dreams. Harry is suddenly "awakened" from each one of them. The first time he meets Lisa is after searching the entire Darkside Hospital. When Harry meets Lisa in the Darker side of the room he met Kaufmann in, he gets to know and like the young nurse. Abruptly, in the middle of the conversation, Harry wakes up in the Misty Silent Hill version of the room he met Kaufmann in. The last time Harry was in this version of Silent Hill, he was in an elevator going between floors. This sort of thing continues throughout the game, with Lisa appearing and disappearing. In case you didn't pick this fact up, Lisa is the one on the confession tape, and the child that she is talking about is Alessa.