Ike Issacs is an artist and slacker who leeches off of his friends. He's attracted to Silent Hill to look for inspiration and realism for his paintings. The town welcomes him and allows him to live a fairly uncomplicated life dedicated to his work. It would seem that the creatures that inhabit Silent Hill enjoy being portrayed and immortalized in art.
Everything is going great for Issacs, he's got no money problems, his paintings are selling (mysteriously) but he is not allowed to leave town. Whenever he gets close to the edge, a mysterious fog brings him back to the center of town.
One day a group of cheerleaders arrives at Silent Hill. They find Ike's place and they make themselves at home which bothers the artist. A pair of cheerleaders are captured by the monsters and Ike is forced to help Cheryl (the captain of the squad) to get them back.
In the end the cheerleaders manage to escape and they leave Ike behind in combat. But a surprise may be awaiting the squad since the two cheerleaders they rescued seem to be changed by the evil in Silent Hill.