The main character of the first Silent Hill, Harry Mason's first encounter with Silent Hill is with his wife when they found a baby girl stranded along the side of the road. Unbeknownst to the couple this young girl was the reincarnated form of Alessa Gillespie, daughter of Dahlia Gillespie a leader of the religious cult "The Order." The couple took Alessa home with them and raised her as their daughter, renaming her Cheryl. When the time came to summon the cult's God residing in Cheryl, Harry and his adoptive daughter were currently on a trip to the town. A ghostly figure of a woman crosses the road in front of them, Harry instinctively tries to swerve out of the way but quickly loses control of the car causing it to crash. When he awakens it is several hours later and daytime, a thick fog covers the entire landscape. He soon realizes that Cheryl has gone missing and he immediately begins his search. With the road leading out of the town mysteriously disappeared, leaving an incredibly high canyon in its wake, he is forced to enter the town of Silent Hill.
As soon as he enters he experiences the town's "Otherworld" and demons, which quickly overwhelms him. Harry wakes up in a diner, further into the town where he finds a police officer Cybil Bennet from Silent Hill's neighbor city Brahms who also happens to be trapped within the city limits. He tries to explain his situation but Cybil only comes off as confused and unbelieving of the impossibility of it all. Two two split up soon after in search for answers as well as any information on his daughter.
After searching for a little while, Harry comes across a woman dressed in tattered robes who turns out to be Dahlia Gillespie. She comes across as very helpful, if not a little weird and paranoid, mentioning that she had seen a little girl heading towards the town's Hospital. After parting ways with the woman, Harry finds his way towards the hospital where he finds the doctor Michael Kaufmann with one of Silent Hill's at his feet. The confrontation only stands to confuse things with the doctor leaving with almost no answers answered. Also in the Hospital he comes across a young nurse named Lisa Garland, the two quickly connect and two quickly commit themselves to finding Cheryl.
Throughout the rest of the game Harry slowly uncovers a dangerous substance trade going on behind the scenes in Silent Hill involving Michael Kaufmann and The Order. It later becomes clear that his daughter Cheryl is much more than she appears to be; half of the town's God, which needs to be reunited with Alessa Gillespie, the other half, and that Dahlia and Kaufmann's possession. He confronts the two but arrives too late. The two girls are merged together to create the beast called "Incubator" which he is forced to kill. Before the creature dies, it gives Harry a second reincarnated child, this time of Alessa and Cheryl in one form. The town quickly returns to normal soon thereafter, and Harry leaves with the child as soon as he can. He renames the child Heather.
The time inbetween the original Silent Hill and the third game for Harry Mason is described mainly through outside interviews and articles posted by the Silent Hill staff. After the game the Harry moves away to Portland where he and Heather live a normal life until members of The Order find their trail. In an attempt to capture Heather and return her to silent hill, one of the cult members met was killed by Harry in self defense. These actions caused Harry to become even more paranoid and conservative in his values. Soon after things settled down, he moved to an unnamed town with Heather and dyed her hair blond in an attempt to disguise her.
They lived in the Daisy Villa Apartments in the unnamed town for twelve years before the events of Silent Hill 3 occur. Harry is now 49. He sends Heather out on an errand, which turns out to be the last time he sees her and hears her voice. He is later murdered in his apartment by the "Missionary" creature sent by Claudia Wolf, one of the leading members of "The Order" in revenge for stealing away the reincarnation of their God.
Behind the Scenes
A voice actor identified only as Michael G voiced Harry Msason in the English version of the original Silent Hill.