"There it is. The freakin' cosmic all. I could be like her. Like whatever it is that's inside old Connie here. A god. A goddess. All-powerful. Worshipped on more worlds than i could dream of. Opposed only by those we allow to stand against us to keep eternity from getting too boring. Torturing souls and having a good old time, reshaping worlds, burning the fuck out of the universe."
—Christabella LaRoache, upon being given "awareness" by Samael, Dead/Alive issue #5.
- First game & 0rigins:
- Dahlia Gillespie is the head of a cult known as the Sect of the Holy Woman. Starting a drug trade, Dahlia sells a hallucinogen made from a local plant named White Claudia to the tourists, killing the anti-drug mayor and the narcotics officer Gucci in the process. Desiring to gain personal power by summoning God, Dahlia kidnaps and attempts to impregnate several young girls with the God, which leads to their deaths. After finding out that her 7-year-old daughter Alessa had vast mental powers, Dahlia decided to perform the impregnation ritual on Alessa. As a result of this, Alessa's soul was split in 2 halves. Dahlia then cast a spell, keeping one half of Alessa alive and in extreme pain, not allowing her burns to heal. Dahlia's intention was for the other half to subconsciously feel Alessa's pain, and come back to Silent Hill, where the soul would be reunited. Seven years later, Dahlia tricks the first game's protagonist Harry Mason into helping her to complete the ritual.
- Dr. Michael Kaufmann produces and supplies PTV for the Order, while keeping much of it to sell elsewhere. Uncaring of the drug's intense effects and painful withdrawal symptoms, Kaufmann greedily lines his pocket, giving the dangerous psychedelic to tourists looking to get high. Preying on his own nurse Lisa Garland, Kaufmann hooks the young woman for years, threatening to cut her off lest she yield to his demands both sexually and for his illegal operations and eventually deciding to flee the town for fear of his own safety, abandoning Lisa to the Order's apocalyptic plot.
- Silent Hill 4: Jimmy Stone and his right-hand man, George Rosten, are the long-deceased leaders of an alliance between the Sect of Valtiel and the Sect of the Holy Mother, branches of the religious cult known as the Order. Running the Wish House with an iron fist, they brainwashed and abused orphans to make more followers of the Order, sending those who disappointed them to a Hellhole Prison where the children would suffer for days, some not even surviving. As representatives of their respective interpretations of the Order's teachings, both are also equally guilty of more atrocities. Stone was given the nickname "Red Devil" for his choice in becoming an executioner to be closer to his twisted angel and Rosten was particularly interested in finding someone to complete the 21 Sacraments, sacrifices that, in his belief, would cleanse the world of sin. Deciding to use the young Walter Sullivan as his puppet, Rosten devoted himself to raising and molding him into his own Serial Killer.
- Judge Margaret Holloway is one of the respected town leaders of Shepherd's Glen and a cold-hearted, cruel and vicious leader of the Order. Years prior, Holloway murdered her youngest daughter Nora by strangling her with her own hands, as per the pact with the Order's God, while barely concealing her own enjoyment at the process. When the pact was broken due to Joshua Shepherd dying in older sibling Alex's place, Holloway reassembled the Order to take control of Shepherd's Glen as a means of gaining and maintaining her power. Over the years she had residents kidnapped to be brainwashed into the Order, with those resisting ending up tortured to death. Eventually the residents were either dead or soldiers for the Order. Later, she plans on killing her other daughter Elle for her refusal to join her, before attempting to torture Alex to death with a power drill.
- Curtis Ackers is a member of Margaret Holloway's Order, one of the first and the most depraved of all members who helped abduct numerous victims into Silent Hill. In the Order to indulge his sadism, Curtis tortures and murders his victims, including children. Even after Margaret is defeated, Curtis makes an attempt to torture her daughter to death with a circular saw, musing how he knows what to do to "take care of her".
- Orphan trilogy: Alessa, a malicious spirit haunting Silent Hill, possesses none of her original counterpart's tragic backstory and is responsible for the deaths of several playable characters. Growing up hating the orphanage she lived in, Alessa possessed her sister, Karen, and committed a massacre that took the lives of numerous children, purely out of spite and to become "awake". Thirty years later, Alessa resurfaces to kill those who survived. After killing two of the survivors, Alessa enlists the help of a revived victim to stop Karen from ruining her plans and later sends the man who had killed their parents, Vincent, to destroy the rest of her, but not before convincing the last survivor, Emilie, to stab herself with a knife. Successfully eliminating Karen, Alessa gives Vincent a heart attack, as he was not useful to her anymore.
- Whately is a vile being from Otherworld, who wants to unleash his brethren upon the Earth to conquer it and feed on humanity. Manipulating the events from afar, Whately sets up unfortunate events in the life of reporter Douglas Brenneman, kidnapping his fiancée and killing police officers to make him chase a story. As Douglas searches for answers, Whately causes people around him to go insane and kill and cannibalize each other, as well as having Dr. Aickmann experiment on countless fertile young women to bring Samael and the rest of his kind to Earth. Later on, Whately unleashes Otherworld on Silent Hill, massacring many people and setting the town on fire. In the end, Whately decides to simply use another young woman, Connie Mills, as a vessel for Samael, while killing several innocent people and framing famous actor Kenneth Carter for them, to spread tales and rumors about Silent Hill to the rest of the world, so that Samael can feed on the fears and nightmares of people who dream of Silent Hill.
- Christabella LaRoache, an undead 8-year-old lurking within the town, once traumatized a film student and murdered her doctor before resurrecting him as her pet monster. Coming face-to-face with her older sister, Christabella amuses herself by killing her friends one by one, intending on making them into more slaves. After having her powers taken away from her, Christabella is recruited as the Psycho Party Member for the heroes, torturing one of them as retaliation for showing disgust towards her. With the destruction of Samael's mortal vessel, Christabella succeeds in becoming the sole ruler of Silent Hill, excitingly advising a visitor that they will know when it is time to scream. Unlike the demonic Whately and his plan to change the entire world, Christabella ruins lives solely to feel powerful.
- The Grinning Man: The Grinning Man is a gunslinging warlock and Serial Killer with a taste for Hunting the Most Dangerous Game. Interested in turning Silent Hill into his own hunting ground, he is introduced exploding a mining complex with a young man inside, and then takes a ride to Silent Hill, abducting the women who had given him a lift, along with the passengers of a van. Keeping them hostage in the Lakeview Hotel, the Grinning Man brands those he captures, including children, with the Mark of the Serpent, which protects them from monsters, but slowly drains their vitality until they die, leaving them zombie-like in appearance.
- Sinner's Reward: Michael "Mad Dog" Stanton, the abusive father of Jack "The Pup" Stanton, only appeared in one flashback, but proved himself to be the one responsible for Jack's misfortunes. Wanting his son to follow in his footsteps as contract hitman, Michael sadistically forces Jack to kill his own dog when he was only eight, beating him for hesitating. Traumatizing the poor boy for life, Michael succeeds in creating a cold-blooded killer out of Jack, who goes on to kill many people, innocent or otherwise, which, in the end, results in Jack's suicide, in an attempt to escape "Mad Dog's" influence.
- The Silent Hill Experience: Hunger: Dr. Aickmann is a histrionic sexual deviant working at Brookhaven Hospital who fully supports Whately's plans of bringing Samael to the human world. Contracted by Whately to be his human accomplice, Aickmann helps him with kidnapping fertile young women and impregnating them with the seed of Samael, in hopes that they would give birth to the demonic god and his brethren. After a woman had been chosen to be the incubator, Aickmann goes on a homicidal rampage, killing a nurse and a number of other people, keeping their eyes around his operating suite as macabre trophies.
- Silent Hill: Christabella is the manipulative leader of the fanatical Brethren. An uncaring religious extremist, Christabella despised her nine-year-old niece, Alessa, for being born out of wedlock, having her condemned as a witch and using her position to encourage the other students at Midwich Elementary to bully and torment Alessa daily. Citing Alessa's rape at the hands of a school janitor as proof that the girl was "filth", Christabella took Alessa to the Brethren's sacrificial chamber and hung her over a bowl of hot coals, slowly burning her alive; the ritual failed and resulted in part of Silent Hill being destroyed by fire. After Christabella and the Brethren became trapped inside Silent Hill, Christabella continued to use their fear to keep them under her control. Believing Sharon to be the Devil's spawn, Alessa burned Cybil alive and was prepared to do the same with the little girl, forcing her sister Dahlia to watch everything.
- Revelation 3D: Claudia Wolf is an albino fanatic who lacks her original counterpart's sympathetic qualities. The sister of both Christabella and Dahlia Gillespie, Claudia is the shapeshifting High Priestess, known as the Missionary, for the Order of Valtiel, who desires to bring Heather back to Silent Hill and summon her enigmatic god to the human world. As an important figure within the cult, Claudia had her own father and a number of other people condemned to the Brookhaven Asylum to be lobotomized while also crucifying supposed traitors. Cutting a symbol into the chest of her own son as part of a ritual that would allow him to find Heather for her, Claudia murders a private investigator who had betrayed her and kidnaps Heather's father, forcing the girl to return to the town. When her son chose to side with Heather, Claudia spared him from being burned alive but instead sent him to suffer the same fate as his grandfather before him.