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Unlike Daniel Garner, the hero of the original Painkiller, who did not deserve to be in Purgatory, it is made abundantly clear why William Sherman does not deserve to pass the pearly gates. An assassin in life, Sherman killed dozens of people for money, only regretting his decisions in life at the very end of it: after rigging a car to explode when his target turned the ignition key, Sherman was horrified to see a public transit bus unexpectedly turning onto the street, where it and everyone aboard would be killed in the resulting explosion. Feeling remorse for the first time in his career, having considered himself a professional killer, not a wanton murderer, Sherman ran into the street from the safety of his hidden observation spot and tried to stop the bus, but failed. The bomb went off, taking Sherman, his target, and the innocent men, women, and children aboard the bus with it.
After dying, Sherman finds himself in Purgatory, wielding a strange weapon called the Painkiller and guided by a mysterious unseen voice, taking him on a bizarre journey through the afterlife.