"Jack-of-Smiles, Fallen London's premier lunatic murderer, has been known to hide inside snowmen until passersby come within reach. 'We award this exploit three marks of ten,' the Magazine Formerly Known As The London Magazine opines. 'Smiles' exploits increasingly tend more to the novel than the genuinely ghoulish.'"[2]
Jack-of-Smiles began his killing spree roughly 20 years ago, around the 1880s, but wasn't given that infamous moniker until a decade later.[3] The name stemmed from his grisly habit of slashing throats and his unsettling, humorless demeanor.[4] Jack has captured both the press and public imagination, inspiring a wealth of literature.[5] Writers who craft sufficiently ghoulish tales of his exploits even receive a personal token of appreciation from Jack himself.[6] However, it's more likely the work of an admirer rather than the killer himself.[7]
The knives Jack uses are cheap, varied in form and material.[8] He primarily hunts in the poorer districts—Spite, dim alleyways,[9] near flophouses,[10] from wanted posters[11] and anywhere suitably disreputable. He has been confronted and stopped numerous times by brave citizens and furious mobs.[12] Hunting Jack has even become a grim pastime.[13] Still, he continues to haunt the city.
Whether this persistence is due to multiple people assuming the role[14] or because the personality of Jack somehow jumps between bodies[15] remains unknown.[16] One thing is certain: Jack does not appreciate being called 'Smiles.'[17] He avoids open confrontation, fleeing when faced with direct resistance,[18] yet he takes revenge on those who vex him—by targeting their friends and family.[19] Though commonly referred to with masculine pronouns, Jack has been known to take female forms,[10] though less frequently.
His combat prowess and agility vary; sometimes he is a skilled and formidable foe,[20][21] while other times he is dispatched with relative ease.[22] Some accounts even suggest he appears in multiple locations simultaneously.[23] Victims who have been "Jackified"—those overtaken by his influence—can sometimes recover. Some recall little of their time as Jack,[24] while others regain their memories with time.[25]
The constabulary has battled Jack-of-Smiles for years,[26] with 37 investigators assigned to his case—only for all of them to eventually become Jack themselves.[27] The devils, well-versed in the marks left on a soul by violence, claim that the Jacks they have captured and abstracted bear no such stain.[28] Whatever causes people to become Jack leaves no physical trace on the body either.[29]
Who is Jack?
"Are you quite sure you want to know this?"
Beyond this point lie major spoilers for Fallen London, Sunless Sea, Sunless Skies, or Mask of the Rose. This may include endgame or major Fate-locked spoilers. Proceed at your own risk.
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Jack is not a single person but a set of sentient, bloodthirsty Polythremean knives.[31] These knives share a single, relentless personality. Anyone who wields one becomes increasingly violent until their own mind is entirely consumed by the knife’s will.[32]
The origin of these cursed blades lies in a failed scheme by Mr Spices,[33] one of the Masters of the Bazaar. Spices sought to create more "flavorful" love stories for the Bazaar, but the plan failed—the Bazaar does not accept artificially manufactured tales of love.[34] To execute the scheme, Spices tricked a man in Polythreme into consuming a special brand of honey that allowed the Master to communicate with him through dreams. Spices convinced the man that his wife was unfaithful. Enraged, the man dreamed of burning down his town; in his honey-mazed state, he had done so in reality.[35]
The Jack knives were forged in an ironworker’s shop that perished in that very fire. The murderous passion that fueled the inferno warped the workshop itself, and every knife forged there emerged imbued with an insatiable thirst for blood.[36] Though Spices' original plan failed, Jack’s resulting infamy proved useful—so the Master allowed, and even encouraged, Jack to persist.[37]
Historical & Cultural Inspirations
Jack-of-Smiles is inspired by Jack the Ripper, the unidentified serial killer who terrorized London’s Whitechapel district in 1888. The Ripper’s victims were primarily impoverished women, many of whom were sex workers in the East End. His murders were particularly gruesome, involving deep throat slashes and severe abdominal mutilations, leaving behind scenes of shocking brutality.
The horror of these crimes gripped Victorian society, and more than a century later, the mystery still captivates the public. Sensationalized media coverage at the time not only fueled widespread fear but also transformed the Ripper into a grim cultural figure. While the murders were undeniably tragic, they became a tool for reformers to highlight issues of poverty, crime, and the failures of law enforcement in London’s most vulnerable communities.
The Ripper’s identity remains one of history’s most infamous unsolved mysteries, spawning a dedicated subculture of amateur criminologists known as "Ripperologists." These enthusiasts meticulously analyze evidence, theories, and suspects, keeping the case alive through endless speculation. Over the years, the Ripper’s story has been adapted into countless books, films, and television series, securing his place as a dark but enduring cultural icon.
↑The Jack-of-Smiles oeuvre, Fallen London"[…] It's been twenty years since Jack first appeared, although he's only been wearing that name for ten. He is sometimes a she, but not often. […] Jack prefers to slit people's throats cloaked in obscurity. Are you any closer?"
↑Sidebar Snippet: Why do they call him Jack-of-Smiles?, Fallen London"The lunatic murderer Jack-of-Smiles earnt his name by his fondness for cutting throats, but also for his humourless demeanour. He takes himself very seriously. Not everyone else does, although a certain class of newspaper reports his exploits with some enthusiasm. Don't call him 'Smiles', they say. He hates that."
↑The Jack-of-Smiles oeuvre, Fallen London"Dozens of penny dreadfuls. A light opera. A stack of academic monographs. Plenty of people have written about Jack. Is any of it useful to you?"
↑Sidebar Snippet: Who is Jack-of-Smiles?, Fallen London"There is no proof for the claim that this villain transmigrates between bodies. The numerous crimson-handed murderers who have cheerfully pleaded guilty to crimes performed with his particular modus operandi are most likely lunatics, or, according to more hysterical accounts, members of the same esoteric society. These madmen have been known to commission penny-dreadfuls detailing the crimes of "Jack". Surely if anything this discredits them further."
↑More Detective Work, Fallen London"The knives vary in form and age and materials, but none of them are expensive. There's no master cutler or weaponsmith to call on. But you'll think of something."
↑Jack be quick, Fallen London"Sometimes Jack favours the wretched rookeries of Spite for his sport. Constables are few and dim-sighted here. But the wrath of the Spite mob is a thing of frenzy and blood. Tonight, they're chasing Jack through the alleys."
↑ 10.010.1The next victim?, Fallen London"You turn to the flophouse's landlady on your way out. It's Smiles! The noxious clouds of smoke from her pipe disguise his (her?) presence and a blade flashes. Your friend is felled with a straight cut to the neck and Smiles runs off giggling."
↑Jack be quick, Fallen London"The mob […] is a headless beast. Anyone with a little savvy or […] speed could outpace it. But it's not half an hour before Jack's end comes […]. Jack is feared and savage, […] not fast or skilled. What does this mean?"
↑A glimpse of a dressing-room, Fallen London"You glance through one of the empty mirror-frames. For a moment, you are surrounded by people. They are changing costumes, putting greasepaint on, brushing wigs out. There is light and noise all around you."
↑Smiles! Put that man down!, Fallen London"Jack-of-Smiles: half-immortal and all nuisance. The indefatigable body-switching murderer is on another killing spree in Watchmaker's Hill. A committee of concerned citizens has requested your help."
↑The clever way, Fallen London"The trail is cold. Jack strikes, apparently at random, and is brought down. How can a detective hope to catch such a... what? Body-hopping soul? Shapeshifting brotherhood? It's enough to make one reach for the violin and the laudanum bottle."
↑Dress up as a victim and wait to be stabbed, Fallen London"[…] You sense something, and turn to a stab of pain in your arm, a leathery face and a voice shrieking 'MY NAME IS NOT SMILES!' You discharge your trusty derringer directly into Smiles' face. […] He'll be back, but you've certainly annoyed him tonight."
↑Jack's claimed dibs!, Fallen London"[…] you run smack into a tall, cadaverous man carrying a very sharp knife. It's Smiles himself! He doesn't like open confrontations, and he turns and bolts. You let him go. You have your target, and you know what face Smiles is wearing these days […]"
↑Mess with the Smile, get the teeth, Fallen London"You've annoyed Jack-of-Smiles once too often! The knife-wielding maniac […] your friends and acquaintances. Some are en route to the Tomb-Colonies […] others are recovering, but […] being repeatedly murdered has caused them to snub you quite rudely."
↑Jack in bandages, Fallen London"[…] you can hear the shrill whistles of Constables. You'll only have to hold him off until they get here. But that's a job. This Jack can fight – […] you notice the regimental jacket over the bandages."
↑Jack on the roof, Fallen London"[…] He leaps ably from rooftop to rooftop, swinging on chimney-pots and dashing through plumes of smoke […] Seconds later, a worn carpenter's knife flashes past your ear and sails downward to clatter on the cobblestones. This Jack will be difficult."
↑Jack-of-Smiles is here!, Fallen London"You race up the stairs […] The inhabitants […] have Jack cornered and are brandishing fire irons.[…] A scream from behind you.[…] You leap through the open window […] Jack is here too […] Two Jacks. That could change everything..."
↑Who are you?, Fallen London"[…] I don't really remember much of that time. […] They tell me I killed four people, one of them for good. […] All I remember is the knife. It was a raggedy old blunt thing […]"
↑Become Jack, Fallen London"[...] You're you again. You're free again. How long have you been Jack-of-Smiles? [...] What have you been doing? Well, that's not hard to guess, but you can't remember. It will come back to you, though. And then you can stop Jack for good."
↑Your turn at it, Fallen London"The Knuckle-Scarred Inspector picks up the box […] and heaves it over to you. "[…] Jack-of-Smiles is your case now. […] Most likely you'll end up Jack, though. […] workin' on the squad, yer oughta uncover new stuff. […] I reckon there's folks out there 'oo know summat.""
↑Number 37, Fallen London"There's a page in the Jack-of-Smiles case notes that bears the signature of each officer to lead the investigation. Thirty-seven signatures, once yours is added. Is that enough? Will there be a thirty-eighth, looking over the notes as you are now?"
↑A friendly fang, Fallen London'We were after him […] years ago. […] The souls were nothing special, though […] Don't you think that's odd? […] that degree of murder usually leaves […] a mark on the soul. Nothing like what happens to the Northridden, but something […]?'
↑Jack's leavings, Fallen London"You have a pair of Jack corpses and a knife. You open a vial of something very nasty to deaden your sense of smell, and you begin […] Whatever is causing Jack to be Jack, it doesn't leave a physical mark that you can see."
↑Jack's Origin, Fallen London"However you came here, you are now sure. Jack-of-Smiles is the result of a set of knives. Knives with more personality than cutlery should have. Knives from Polythreme."
↑Finding a knife, Fallen London"The tip of the blade has snapped off. Blood. The handle is worn. It's not […] sharp. Cut them to little pieces. Not the weapon one would choose […]. Revenge. Blood. You fling the knife away […] It's the knives. Jack's in the knives."
↑To the garden, Fallen London"So, yes, we constructed the entity that became known as Jack-of-Smiles in your gutter press. Dreams and our agent and honey and so forth. And if you put store in such trifles, we consider the whole business regrettable. Most regrettable. You understand that it did not work."
↑To the garden, Fallen London"[...] The Bazaar has... appetites. And it is one of our many duties, along with that sodden villain Wines, to fulfil those needs. [...] Using the unnatural vitality of the first customer's lover, we created Jack. For what inspires love, more than the threat of death? Such was our thinking at the time. Misguided of course. We know that now. The Bazaar does not accept stories of such synthetically created romance. [...]"
↑Find out its history, Fallen London"THERE WAS A GROUP OF THEM. YOU WOULD SAY A 'FAMILY'. THE MAN TOOK HONEY. HE DREAMED. SOMEONE TOLD HIM IN DREAMS THAT THE WOMAN CARED ONLY FOR ANOTHER. HE DREAMED OF BURNING DOWN THE TOWN. BUT HE WAS MAZED IN DREAMS. HIS BODY CAME BACK BEFORE HIS MIND. AND HE TOOK THE LAMP OIL AND THE MATCHES AND HE BURNED THEM."
↑To the garden, Fallen London"[...] A terrible business. But still. We see that Jack-of-Smiles has a certain laudable effect on public order and the attention of the press. So we have had the building in question moved. Jack-of-Smiles lives another day. Now leave us. We wish to be alone."