The five serial killers, also referred to as the Heralds of the Apocalypse or simply The Five, are Legion's enforcer who wreak havoc in the world of the living, Liveside. They are all psychopatic serial-killers who were turned into undying half-demons
The Five are:
1. Marco Cruz
2. Milton Pike
3. Avery Marx
Mama Nettie's file in the game contains their profiles, as compiled by NYPD cop Thomas Deacon. The notes consist of sketches, general information about the killers, and the poems they left on the crime scenes.
None of the Five are mortal men any more, as they each carry one Dark Soul. When they take damage in combat or are almost beaten, their appearance starts to resemble that of a Trueform. To defeat them, Shadow Man has to destroy them with the Shadowgun after they take enough damage.
The only member of the Five in both the game and the comic book adaptation Jack the Ripper, here described as the mightiest of the Five and implied to be their leader.
There is also John Douglas Barber, a psycho who killed over twenty-six people, and nearly got Shadow Man's friend Astrid Lockier; a mad artist who was badly burned by Shadow Man after attempting to harness the power of the Lwas, the Divine Spirits of Voodoo; a demented, Russian expy of Jeffrey Dahmmer named Piotr Pribluda; and the chainsaw maniac Earl Godsey.