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Paint It Black follows the story of Ike Isaacs, an artist who finds himself homeless after being kicked out of a friend's apartment. Ike has been suffering artist's block, until he meets a stranger who claims to have visited the ghost town of Silent Hill. The stranger informs Ike that he was able to leave the town because his own friend sacrificed himself. This story inspires Ike to travel to the town to seek out the truth behind it.

Oddly, the monsters of the town do not attack Ike, instead allowing him to paint them. Inspired, Ike is able to paint again; his portraits now feature the creatures that live in the town, and he has found that he is unable to leave. Moreover, his paintings have somehow been leaving and are being sold to rich clients outside of Silent Hill.

The story then takes an unusual turn as a team of cheerleaders arrive in Silent Hill looking for some friends who they believe went missing in the town. As the plot continues to follow a strange set of developments, Ike discovers that he can actually travel through his paintings and he attempts to use them to escape. His attempted escape fails and he finds that the cheerleaders have turned on him, sacrificing him so they can leave town. Because of his alliance to the cheerleaders, the monsters turn on Ike.