Rogue Backstory Generator: A First Theft, a Teacher, One Rule

Press New backstory for a rogue's past in six parts: a first theft, a teacher, a trade and one rule.

Rogue Backstory Generator: A First Theft, a Teacher, One Rule: 30 backstories

First took a boot, thinking it was their own. Learned from the dog that guarded the bakery. Works as a stand-in for people who are out of town. It went wrong when the clock they were timing by had stopped. Looked for by a detective with a new notebook and no cases yet. One rule: never takes a child's toy.

Padlock: keep a part. Arrows: change only that part.

First tooka boot, thinking it was their own
Learned fromthe dog that guarded the bakery
Works asstand-in for people who are out of town
It went wrongwhen the clock they were timing by had stopped
Looked for bya detective with a new notebook and no cases yet
One rulenever takes a child's toy

Set a timer

5:00

Next one automatically Sound

History (0)

Every backstory you make is kept here, newest first, up to the last 20. The list stays in this browser.

Backstory of the day

First took a boot, thinking it was their own. Learned from the dog that guarded the bakery. Works as a stand-in for people who are out of town. It went wrong when the clock they were timing by had stopped. Looked for by a detective with a new notebook and no cases yet. One rule: never takes a child's toy.
First took an apple from the bottom of the pile. Learned from a crow that stole shinier things than they did. Works as an eraser of names from lists. It went wrong when they opened the wrong house, perfectly. Looked for by a schoolteacher whose exam they sold. One rule: never takes the only copy.
First took a doorknob they simply liked. Learned from a merchant who overcharged them and explained how. Works as an agent for an invented duchess. It went wrong when they fixed the lock on the way out. Looked for by a farmer whose prize pig went missing for a week. One rule: always leaves one coin.
First took a scarecrow's coat on a cold night. Learned from a pawnbroker who asked no questions twice. Works as a thief-taker who used to be the thief. It went wrong when the buyer turned out to be the owner. Looked for by a goldsmith who made the thing they took. One rule: always locks up after themselves.
First took one chess piece from every set in town. Learned from a cat that got into every larder it liked. Works as a shadow for hire. It went wrong when the crew voted, mid-job, to go home. Looked for by a baker still owed for forty pies. One rule: never takes a wedding ring.
First took one glove, not the pair. Learned from losing every game of hide and seek until they won. Works as a fence for things with no past. It went wrong when the portrait on the wall looked like their mother. Looked for by a farmer whose prize pig went missing for a week. One rule: always leaves by the front door.
First took a ring from a sleeping uncle's finger. Learned from a year of deliveries to every back door in town. Works as a plant in a street magician's crowd. It went wrong when both of them thought the other had the bag. Looked for by a statue the town put up to thank the wrong person. One rule: replaces what they took with something handmade.
First took a grandmother's thimble. Learned from a cousin who talked their way into every party. Works as an opener of other people's luggage. It went wrong when the newest member wrote their name in the dust. Looked for by a hound from an old job, whiskers gone white. One rule: never whistles indoors on a job.
First took a loaf cooling on a kitchen sill. Learned from a brother who kept two sets of school reports. Works as a dealer in lost property. It went wrong when the getaway boat was tied with a real knot. Looked for by a museum director with an empty plinth. One rule: always locks up after themselves.
First took a master's signature, copied until it matched. Learned from a wandering actor with nine accents. Works as a lifter of things from high shelves. It went wrong when the collector kept the real one in the bread bin. Looked for by a collector outbid with a banknote drawn by hand. One rule: always wipes their feet.
First took a master's signature, copied until it matched. Learned from a peddler whose cart had a second floor. Works as a pickpocket who puts the wallets back lighter. It went wrong when a baby woke and they sang it back to sleep. Looked for by a newspaper artist paid by the sketch. One rule: always returns it if asked nicely.
First took the last pear from the tree over the wall. Learned from the old thief whose patch they wandered into. Works as a shadow for hire. It went wrong when it snowed and every step showed. Looked for by a first partner who went honest and wants company. One rule: never takes a tool someone earns with.
First took the good scissors from the sewing box. Learned from the shopkeeper who caught them and hired them. Works as a carver of official stamps. It went wrong when the strongroom held one card reading: too slow. Looked for by a child who believes they are a hero. One rule: never takes the last of anything.
First took a boot, thinking it was their own. Learned from nobody: a broken padlock and a long winter. Works as a wearer of nine uniforms. It went wrong when the distraction ran out of songs. Looked for by a playwright who put them in a comedy. One rule: never takes a child's toy.
First took a loaf cooling on a kitchen sill. Learned from a grandfather who did coin tricks at every dinner. Works as a seller of gossip by the ounce. It went wrong when they timed the guards and forgot the cleaners. Looked for by a statue the town put up to thank the wrong person. One rule: never takes a pet, however willing.
First took a name that sounded better than their own. Learned from a conjuror's assistant who did the real work. Works as a forger of signatures. It went wrong when the alibi was at the same party as the owner. Looked for by a retired judge who does it as a hobby. One rule: never takes the only copy.
First took a letter meant for the house next door. Learned from a letter carrier who read every postcard. Works as a printer of invitations to closed parties. It went wrong when the diamond was paste and the owner knew it. Looked for by a rival who cannot retire until they do. One rule: never starts a job on a Friday.
First took a bottle of ink from a stationer. Learned from a year of deliveries to every back door in town. Works as a shadow for hire. It went wrong when the strongroom held one card reading: too slow. Looked for by a mapmaker who needs a way into a walled garden. One rule: always wears one odd sock.
First took a tool they always meant to bring back. Learned from a rival's lookout who whistled better. Works as an eraser of names from lists. It went wrong when the driver went to the wrong bridge. Looked for by a retired judge who does it as a hobby. One rule: never takes a pet, however willing.
First took their own apprenticeship papers. Learned from a year of deliveries to every back door in town. Works as a copier of maps with the best road left off. It went wrong when the key broke off in the lock. Looked for by a child who believes they are a hero. One rule: never takes a thing somebody talks to.
First took the blame for a broken jug, for a fee. Learned from a rival's lookout who whistled better. Works as a mapper of other people's houses. It went wrong when the merchant had already sold it twice. Looked for by a records keeper missing exactly one page. One rule: never takes a pet, however willing.
First took one chess piece from every set in town. Learned from a street artist who drew faces from memory. Works as a keeper of a very private warehouse. It went wrong when the disguise matched a wanted notice. Looked for by a parrot that learned their real name. One rule: never takes a pet, however willing.
First took a teacher's chalk, every piece of it. Learned from the old thief whose patch they wandered into. Works as a mapper of other people's houses. It went wrong when they opened the wrong house, perfectly. Looked for by a rich recluse with one impossible job. One rule: never lies to a partner.
First took a wheel of cheese that rolled their way. Learned from a great-aunt with a hollow walking stick. Works as a keeper of other people's diaries. It went wrong when the painting was nailed, glued and wired to a bell. Looked for by a former partner who wants their half. One rule: never works on their own birthday.
First took the punchline of another child's joke. Learned from nobody: a broken padlock and a long winter. Works as a painter of last week's old masters. It went wrong when the strongroom held one card reading: too slow. Looked for by a mapmaker who needs a way into a walled garden. One rule: never lies to a partner.
First took a teacher's chalk, every piece of it. Learned from a river pilot who knew every unwatched landing. Works as a listener at keyholes. It went wrong when the owner offered them a chair and soup. Looked for by a baker still owed for forty pies. One rule: always greets a crow by name.
First took the spare coin from a father's coat. Learned from a locksmith who sold them a lock they could not beat. Works as a fence for things with no past. It went wrong when a baby woke and they sang it back to sleep. Looked for by a farmer whose prize pig went missing for a week. One rule: always wears one odd sock.
First took a look at the map on the captain's table. Learned from a bookbinder who could age paper in an afternoon. Works as a keeper of other people's diaries. It went wrong when the key broke off in the lock. Looked for by an inventor who needs a lock tested. One rule: never crosses a threshold left foot first.
First took a wedding cake's top tier, believing it spare. Learned from a peddler whose cart had a second floor. Works as an opener of other people's luggage. It went wrong when the distraction ran out of songs. Looked for by a choir that lost its only silver cup. One rule: always returns it if asked nicely.
First took a mayor's hat, for the length of one street. Learned from a retired customs officer with regrets. Works as a picker of desk drawers in quiet offices. It went wrong when the painting was nailed, glued and wired to a bell. Looked for by a baker still owed for forty pies. One rule: always greets a crow by name.

Next step Design how this rogue looks today Get a pose to draw them in

First took: all 60 first thefts

From home 12

a dog that already wanted to follow them The dog is doing the stealing. Draw the rope slack and the tail going.
a grandmother's thimble Tiny object, big guilt. Show it held between finger and thumb at arm's length.
a letter meant for the house next door Reading at the gate, the envelope opened far too neatly.

Show all 60 first thefts (57 more)

From home, continued

a loaf cooling on a kitchen sill Draw the clean square of sill where the loaf sat, with crumbs leading off the page.
a ring from a sleeping uncle's finger A hand hanging off an armchair, one finger paler where the ring was.
a sister's place in the bread line Two children the same height. Only one of them is looking at the baker.
a spoon of jam from a locked cupboard A chair pushed up to the shelf and a lid not quite back on.
the blame for a broken jug, for a fee They hold the handle and a coin. The sibling in the doorway holds neither.
the good scissors from the sewing box The box lid open, one felt slot empty in a row of full ones.
the last pear from the tree over the wall Only an arm and a pear show above the bricks.
the spare coin from a father's coat A coat on a hook with one pocket turned slightly out.
their own apprenticeship papers A drawer left open and a folded paper going into a boot.

From the street 12

a bell from a goat's collar Fist closed tight to stop it ringing. The goat looks personally offended.
a bottle of ink from a stationer A black thumbprint on everything they touch for the rest of the day.
a busker's best corner, by turning up early Not a thing but a place. Draw them on the corner at dawn with a case open.
a candle stub from a chandler's sample tray One gap in a tidy pyramid of candles.
a handful of nails from a builder's bucket Pockets sagging, walking carefully so nothing chimes.
a hat from a stand outside a shop It is far too big. The brim rests on their ears.
a kite whose string had simply come loose Catching it one street away, already winding the string as if it were theirs.
a pie off the rack behind a bakery counter Steam still rising from the gap in the row of pies.
a ribbon off a market stall Wound round the wrist under a sleeve, one bright end showing.
a seat on a coach they had not paid for Feet on the luggage rack, face behind a borrowed newspaper.
an apple from the bottom of the pile The pile is mid-collapse behind them. They have not noticed yet.
one glove, not the pair A single glove tells the viewer it was a dare, not a need.

From a master or a school 12

a day off, with a forged note Lying in long grass with the note folded into a paper boat.
a ledger page nobody was meant to read One torn stub in a thick book, shown from above.
a look at the map on the captain's table Redrawn from memory on a napkin, with one coast confidently wrong.
a master's signature, copied until it matched A page covered in the same name, the last few flawless.
a porter's uniform off the laundry line Sleeves rolled four times. The badge sits near the elbow.
a recipe the cook swore was secret Flour on one cuff and a look of complete innocence.
a rubbing of the shop's best lock Thin paper held up to a window, the pattern showing through.
a teacher's chalk, every piece of it A bulging sock that leaves white dust on the floor.
a tool they always meant to bring back Still in their kit years later, the handle worn to their grip.
the answers to a test they had already passed Pointless and perfect. Draw the smirk, not the paper.
the clerk's stamp, for one afternoon An inky circle on the back of the hand that they forgot to wash off.
the prize at a jam contest, by swapping labels Two jars, two labels, and glue still wet on a fingertip.

On a dare or by mistake 12

a boot, thinking it was their own Two left boots on one pair of feet.
a bucket of paint and one long wall No theft left to see: only a very large, very new mural.
a horse that was going home anyway The horse leads. They sit facing the tail, arguing with it.
a mayor's hat, for the length of one street Walking very upright, so the hat thinks it is still on the mayor.
a parade's lead drum, by joining the parade Marching at the front with total confidence and no rhythm.
a place in a queue, with a made-up errand Leaning in with a folded paper that is blank on both sides.
a scarecrow's coat on a cold night The scarecrow stands in its shirt, somehow looking colder.
a weathervane, on a dare Coming down a ladder with a brass rooster under one arm.
a wedding cake's top tier, believing it spare One tier gone from a tall cake and a plate held like evidence.
a wheel of cheese that rolled their way Arms spread, knees bent, honestly only trying to stop it.
the flag from the top of a pole Tied round the waist on the way down, the pole still swaying.
the wrong coat from a crowded peg Hands finding unfamiliar things in the pockets one by one.

Small and odd 12

a button from every coat at a party Threaded on one long string and worn like a necklace.
a doorknob they simply liked Polishing it on a sleeve. There is no door for miles.
a marble that was already cracked Held up to one eye so the crack splits the view.
a name that sounded better than their own Signing with a flourish, then checking how it is spelled.
a pawn shop's window display, one item a week The window slowly empties across a four-panel strip.
a shadow, or so they told the smaller children Running with a black cloth flapping behind and three believers chasing.
a spoon from every inn they ever slept in A roll of cloth opened to show twenty spoons, none matching.
a whole street of door numbers Rehung in a new order. Draw the confused postman.
the dot from above a letter on a shop sign A small painted disc in the palm and a sign that now reads slightly wrong.
the last page of a library book A book that ends mid-sentence and a folded page in a hatband.
one chess piece from every set in town A pocket of mismatched knights spilled on a table.
the punchline of another child's joke Telling it first, to the same crowd, while the owner glares.

How this list was compiled: Original list written for Draw This Next, September 2026. Every entry is small, harmless and a little funny, because a first theft tells a viewer who the character was before they were any good at it. Nothing here was taken by force and no entry says how a lock or a pocket is beaten. The notes on what to draw are our own suggestions. Licence: own work

Learned from: all 60 teachers

Family 12

a brother who kept two sets of school reports One satchel with a false bottom and two very different handwritings.
a cousin who talked their way into every party Two figures at a doorway, one already inside taking a coat.
a father who measured every room by habit Pacing heel to toe along a wall while pretending to admire a painting.

Show all 60 teachers (57 more)

Family, continued

a godparent nobody in the family would discuss An empty chair at the table with a very expensive coat over it.
a grandfather who did coin tricks at every dinner His hands in the drawing are never fully open.
a grandmother who haggled for sport A market stall and a seller already wiping their brow.
a great-aunt with a hollow walking stick The stick rattles. Show her shaking it by one ear.
a locksmith aunt who lost keys on purpose Her key ring hangs on their belt now, too heavy for the belt.
a mother who could read a letter upside down Draw both of them at a clerk's counter, leaning the same way.
a stepfather who mended clocks and opened safes Tiny screwdrivers in a row, sorted by size, never out of order.
an older sister who never once got caught She stands in the background of the scene, waving at a guard.
twin uncles who finished each other's alibis Mirror their poses. Only the hats differ.

Honest trades, mostly 12

a bookbinder who could age paper in an afternoon Tea stains, a hot iron and a row of pages drying on a line.
a chimney sweep who knew every roof in town Soot to the elbows and a map chalked on slate.
a letter carrier who read every postcard A sack over one shoulder and a great deal of local knowledge.
a museum guard counting the days to a pension Asleep in a chair, the lesson being how long he stays that way.
a night porter who knew which stairs creaked Chalk marks on alternate steps, climbing out of frame.
a pawnbroker who asked no questions twice Scales on the counter and one raised eyebrow.
a piano tuner with very quiet shoes Felt soles, a tuning fork, and a head tilted to listen through a door.
a retired customs officer with regrets He points at what to look for. They note what he misses.
a rope walker from a wintering circus Balance pole across the shoulders, used here to cross between two roofs.
a ship's purser who kept two ledgers Ink on both cuffs, in two different shades.
a stage magician between engagements Scarves coming out of a sleeve at the wrong moment.
a tailor who sewed pockets inside pockets Turn the coat inside out for the viewer: it is all pockets.

Met on the road 12

a beekeeper who moved calmly on principle Slow hands. Draw the bees ignoring both of them.
a bell ringer who climbed for the view Legs dangling from a tower window, pointing out which shutters are loose.
a coach driver who knew when to look away Hat brim down, reins loose, studying a distant hill with great care.
a conjuror's assistant who did the real work Long fingers, short nails, and a deck fanned in one hand behind the star.
a fortune teller who was right suspiciously often She watches hands and boots, never the cards.
a peddler whose cart had a second floor Boards lifted to show the real stock under the pots and pans.
a puppeteer who worked a crowd with one hand One hand in a puppet, the other showing them where everyone is looking.
a ratcatcher who went where no one checks Coming up through a cellar hatch with a cage and a calm expression.
a river pilot who knew every unwatched landing A hand-drawn chart with certain bends marked by a small star.
a street artist who drew faces from memory A sketchbook of strangers, each with one telling detail circled.
a tinker who could open anything with a spoon A bent spoon kept in the hatband like a feather.
a wandering actor with nine accents The same face nine times across the page, each a different person.

Rivals who taught by winning 12

a girl from the next street who was always first Arriving at a window to find it open and a ribbon tied to the latch.
a guard who walked them home instead A large hand on a small shoulder and a talk that took the whole street.
a little brother who told on them every time Small, loud, pointing. They learned to plan for witnesses.
a locksmith who sold them a lock they could not beat A padlock on a chain round the neck, still shut after all these years.
a magistrate's clerk who spotted every forgery Corrections in the margin, in a far better hand.
a merchant who overcharged them and explained how A receipt as long as an arm, annotated.
a rival's lookout who whistled better Two figures on facing rooftops, each pretending not to see the other.
a schoolmaster who set traps for cheats Ink that turns the fingers blue for a week.
the dog that guarded the bakery Level stare, low growl. They learned patience on the other side of a fence.
the first mark they failed to fool Sitting across a table, calmly sliding the fake coin back.
the old thief whose patch they wandered into A chalk line on the cobbles and a cane tapping it.
the shopkeeper who caught them and hired them An apron thrown at their chest. Catching it is the job interview.

Nobody, exactly 12

a book with the last chapter torn out They guessed the ending and have been guessing ever since.
a cat that got into every larder it liked Following it at a distance, taking notes.
a clockwork toy they took apart and rebuilt One spare gear left over, kept as a charm.
a crow that stole shinier things than they did The crow's hoard on a ledge, with one item that used to be in their own pocket.
a locked door in their own house Years of trying. The scratches round the keyhole are at three different heights.
a puzzle box that arrived with no sender Forty moves to open. They can now do it behind their back.
a stage play about a clever thief, seen nine times Lips moving along with the lines from the cheapest seat.
a year of deliveries to every back door in town A basket on one arm and a memory for latches.
losing every game of hide and seek until they won A child's shoes showing under a curtain, then no shoes at all.
the mistakes of everyone caught before them A wall of old wanted notices studied like a textbook.
nobody: a broken padlock and a long winter A table of lock parts laid out in the order they came apart.
watching a conjuror from the wrong side of the stage Draw the view from the wings: every secret visible, the audience a blur.

How this list was compiled: Original list written for Draw This Next, September 2026. Each teacher is one person or thing with one habit, so that a second figure can stand in the drawing beside the rogue. No teacher is cruel and none is named after a figure from a game, a book or a film. The notes on what to draw are our own suggestions. Licence: own work

Works as: all 60 lines of work

Locks and pockets 12

burglar of bakeries and nowhere else Flour footprints leading away from every scene.
cat burglar who has never woken a cat Tiptoe pose over a sleeping cat stretched across the whole hallway.
copier of keys from one good look A key drawn in the air with a finger while the real one hangs on a hook.

Show all 60 lines of work (57 more)

Locks and pockets, continued

lifter of things from high shelves A long pole with a loop, kept in three screw-together pieces.
lock-picker A roll of thin tools on the knee and an ear close to the door.
opener of other people's luggage A neat row of trunks, each closed again with the straps one hole off.
opener of safes for owners who lost the number Stethoscope optional. A chalked row of tried numbers is funnier.
picker of desk drawers in quiet offices A paperclip, a lamp turned low and a clock showing lunchtime.
pickpocket who puts the wallets back lighter Draw the return, not the take: a wallet sliding home into a coat.
rooftop climber Soft shoes, chalked fingers and a skyline seen from above the chimneys.
sleight-of-hand artist One hand shown doing nothing in particular. That is the busy one.
window specialist Half in, half out, one leg over the sill, listening.

Paper and ink 12

bookkeeper with a second book One ledger on the desk and one flat under the blotter.
carver of official stamps A row of stamps with cork handles, each worn by a different thumb.
copier of maps with the best road left off Two maps side by side. Only one shows the shortcut.
eraser of names from lists A list with a pale rubbed patch and a breadcrumb used as the rubber.
forger of seals Wax, a candle and a carved potato drying beside them.
forger of signatures Three pens in the fist and a tongue between the teeth.
keeper of other people's diaries A shelf of locked little books and no visible keys.
maker of travel passes A stack of blank cards and one finished pass held to the light.
painter of last week's old masters Cracks painted on with a single hair. An oven stands open behind.
printer of invitations to closed parties A small hand press and a guest list with one extra line.
seller of treasure maps drawn last night The ink is still wet. A coffee ring passes for age.
writer of letters of introduction A grand letter addressed to someone who has never heard of them.

Talk and disguise 12

agent for an invented duchess A framed portrait carried everywhere. It is of nobody.
bidder who drives the price up for a cut A raised paddle at the back of an auction room, face in shadow.
false inspector of weights and measures A clipboard, a frown and a ruler that is slightly short.
guest nobody invited Plate full, deep in talk with the host, name tag blank.
impostor of minor nobles The clothes are right. The shoes give it away, so hide the shoes.
plant in a street magician's crowd The one face in the audience that looks too surprised.
professional lost child, now grown Still has the wide eyes. Uses them at ticket barriers.
seller of bridges they do not own Arm sweeping toward a bridge, deed already rolled in the other hand.
stand-in for people who are out of town Wearing someone's coat and learning their walk in a mirror.
talker who keeps a doorway busy Hands spread mid-story while, behind the listener, a door stands open.
teller of fortunes that come true by Friday They arrange the future themselves, on foot, after dark. Show the tired boots.
wearer of nine uniforms A coat rack as the portrait: porter, guard, cook, clerk, conductor.

Things that move at night 12

carrier of sealed boxes, no questions The box ticks, or purrs. Their face stays politely blank.
dealer in lost property A stall of single gloves, each with a story and a price.
driver who waits round the corner Reins loose, engine or horse idling, eyes on a pocket watch.
fence for things with no past A back room of labelled shelves and a magnifying glass on a chain.
keeper of a very private warehouse A plain door, three locks and a welcome mat.
mover of paintings between frames An empty gilt frame on the wall and a rolled canvas inside a hollow cane.
night boatman Muffled oars and a boat sitting lower in the water than it should.
night carter for households that move in a hurry A wardrobe on a handcart at midnight, the wheels wrapped in rags.
pigeon keeper for secrets Birds with tiny tubes on their legs and a loft above a laundry.
runner of letters nobody should read Sealed envelope held away from the body like something hot.
smuggler of banned books A coat lined with paperbacks, standing very square.
smuggler of tea Crates stamped as something dull, and one corner leaking leaves.

Eyes and ears 12

collector of debts and promises A notebook of names, most crossed out, a few underlined twice.
finder of things that were not lost Presenting a bracelet to its puzzled owner, hand out for the reward.
listener at keyholes One knee down, hair tucked back, a glass tumbler against the door.
lookout Leaning on a lamp post with a newspaper held exactly level with the eyes.
mapper of other people's houses Floor plans paced out in the snow of their own yard.
recoverer of stolen goods, for a fee Carrying a painting back in through a front door in daylight.
seller of gossip by the ounce Whispering behind a glove while a small scale tips.
shadow for hire Always half a street back. Draw them as the small figure in someone else's portrait.
spy for whichever side asks first Two letters of thanks in one pocket, from opposite sides.
tester of locks, paid by the owners A printed report card tied to a doorknob: could do better.
thief-taker who used to be the thief Reading a scene the way a cook reads a recipe.
valuer who names the price before the theft A loupe in one eye at a party, studying a necklace across the room.

How this list was compiled: Original list written for Draw This Next, September 2026. Each trade is named by a noun and never explained: no entry says how a lock, a pocket or a signature is beaten, and none involves a weapon or a gang. The meanings of fence (a person who buys stolen goods to resell them) and of lock picking (opening a lock without its key) were checked on 2026-09-30 against https://en.wikipedia.org/wiki/Fence_(criminal) and https://en.wikipedia.org/wiki/Lock_picking. The notes on what to draw are our own suggestions. Licence: own work

It went wrong: all 60 failed jobs

Plain bad luck 12

when a parade came down the escape route Carrying a sack against the flow of a marching band.
when it snowed and every step showed One clean line of prints across a white yard, ending at their boots.
when the cart they hid in was going to the jail Peering from under a tarpaulin at a very familiar gate.

Show all 60 failed jobs (57 more)

Plain bad luck, continued

when the clock they were timing by had stopped Checking a watch against a tower clock whose hands point at different hours.
when the dog turned out to be friendly and loud A delighted dog on its hind legs and a figure frozen with one finger to the lips.
when the empty shop had a night baker Two people in a doorway, both holding trays, both surprised.
when the fog lifted an hour early Caught mid-step on a rooftop in sudden, total daylight.
when the house turned out to be hosting a party A window opened on forty faces and a cake.
when the key broke off in the lock Holding the bow of the key and looking at it like a bad hand of cards.
when the one cloud in the sky moved on A long sharp shadow thrown across a wall, hat and all.
when the rope was one floor short Hanging at the end of it, studying the gap with mild interest.
when the wind took the whole plan off the table Papers flying over rooftops and one hand closing on nothing.

A bad plan 12

when the alibi was at the same party as the owner Two people comparing notes across a punch bowl.
when the borrowed uniform still had a name in it Answering to the wrong name a moment too late.
when the crate marked as the prize held pickles A crowbar, a lifted lid and a smell.
when the disguise matched a wanted notice Standing beside a poster that wears the same false beard.
when the forged pass spelled the town wrong A guard's thumb resting on one word. Nobody speaks.
when the getaway boat was tied with a real knot Kneeling on a jetty, working at a knot with their teeth.
when the ladder was on the other side of the wall Sitting on top of the wall, looking down at the ladder they meant to bring.
when the map was of the building next door Unrolling the plan in a broom cupboard that should be a vault.
when the safe held only another, smaller safe A row of safes in falling sizes, like nesting dolls.
when the secret passage came out in the kitchen Stepping from behind a dresser into the middle of breakfast.
when they opened the wrong house, perfectly A flawless entry into a room with nothing in it but a rocking horse.
when they timed the guards and forgot the cleaners A mop bucket rolling slowly out of the dark at the end of a gallery.

A partner's fault 12

when both of them thought the other had the bag Two pairs of empty hands held up at the same time.
when the buyer turned out to be the owner Unwrapping the goods for a customer who goes very quiet.
when the crew voted, mid-job, to go home A show of hands in a dark corridor.
when the distraction ran out of songs A busker checking their pockets for one more tune while the crowd drifts.
when the driver went to the wrong bridge Two figures waving at each other across a wide river.
when the forger grew proud and added a flourish A document far too handsome to be real.
when the inside contact told everyone at dinner A long table of interested faces turning as one.
when the lookout stopped to pet a cat A whistle that never came and a cat having a lovely evening.
when the lookout whistled the wrong tune Everyone below starts dancing instead of leaving.
when the newest member wrote their name in the dust A proud signature across a dusty piano lid, in full.
when their partner fell for the mark's dog Leaving with the dog and nothing else.
when their partner sneezed in the wardrobe Coats swinging. A hand already rising to cover a second sneeze.

Their own conscience 12

when a baby woke and they sang it back to sleep Rocking a cradle with one foot, sack forgotten by the door.
when the mark turned out to be saving for a wedding A jar of coins with a ribbon and a label in careful letters.
when the old man mistook them for his grandchild Trapped on a sofa under a blanket and a photograph album.
when the owner offered them a chair and soup Sitting at a kitchen table with the bag still on one shoulder.
when the portrait on the wall looked like their mother Hat off in an empty hall, unable to meet the painted eyes.
when the purse held a letter that needed posting Standing at a postbox with someone else's stamp money.
when the shop was already going out of business A closing-down sign, read slowly, with the bag going slack.
when they fixed the lock on the way out Oiling a hinge by moonlight out of professional pride.
when they put half of it back and were seen Caught returning things, which nobody believed.
when they saw the child's drawing pinned inside A crayon picture on a safe door and a hand that cannot turn the dial.
when they stayed to finish the owner's jigsaw Dawn at the window and the last piece going in.
when they stopped to water a dying plant A watering can in the hand that should hold the bag.

The mark was cleverer 12

when the bag they lifted was full of somebody's knitting An open sack, three balls of yarn and half a sock.
when the collector kept the real one in the bread bin Shown too late: a tin on a shelf they walked straight past.
when the countess asked them to steal it for her Being handed the necklace, the plan and a bill for services.
when the diamond was paste and the owner knew it A stone held to a candle that throws no fire at all.
when the dog had been trained to fetch thieves Being walked to the gate by the sleeve, firmly and without malice.
when the guard had read the same book on disguises Two people in identical false beards, mid-nod.
when the house they cased was a locksmith's school Every door a different lock and a bell on each.
when the ledger was written in a private shorthand Pages of loops and hooks, turned one way and then the other.
when the merchant had already sold it twice Three buyers arriving at one warehouse door.
when the painting was nailed, glued and wired to a bell Leaning very still with one corner of a frame in each hand.
when the strongroom held one card reading: too slow A single card propped on a bare shelf, signed with a smile.
when the widow had been a thief first and better She pours two cups without turning round.

How this list was compiled: Original list written for Draw This Next, September 2026. Every failure is told without injury: nobody is hurt, and the worst outcome is embarrassment, a long walk home or an empty bag. The notes on what to draw are our own suggestions. Licence: own work

Looked for by: all 60 pursuers

The law, more or less 12

a border guard who collects their false names A corkboard of passes, all the same face, each a different name.
a clerk who never forgets a face Thick glasses and a sketch pinned over the desk, eerily accurate.
a constable three days from retirement Walking slowly on purpose, hoping not to find them.

Show all 60 pursuers (57 more)

The law, more or less, continued

a customs officer who counts everything twice Finger moving down a list, lips moving with it.
a detective with a new notebook and no cases yet Coat too big, pencil too sharp, eyes missing nothing.
a dock inspector who knows every hull by sight Squinting across the water at a boat that sits too low.
a magistrate who wants one question answered A summons with a single line and a great deal of blank paper under it.
a night watchman who took it personally The same route every night, with a new padlock held like a trophy.
a patient bailiff with a folding chair He sits outside wherever they sleep. Draw the chair, the flask and the calm.
a records keeper missing exactly one page A book held open at the gap, carried from town to town.
a rent collector who keeps every receipt A small black book with a string to mark the page.
a retired judge who does it as a hobby A garden shed turned into a case room, with seedlings on the sill.

People they wronged 12

a baker still owed for forty pies Arms folded, apron floury, bill pinned to the door with a rolling pin drawn beside it.
a bride whose cake arrived one tier short Years on, she still measures every cake she sees.
a choir that lost its only silver cup Twelve singers searching in two-part harmony.
a collector outbid with a banknote drawn by hand Holding the note up to a window, admiring it in spite of everything.
a duchess who wants the necklace and an apology In that order. Draw her writing the apology for them to sign.
a farmer whose prize pig went missing for a week The pig came back fatter and wearing a ribbon. Questions remain.
a goldsmith who made the thing they took She would know her own work anywhere and checks every neck and wrist.
a landlord owed two winters of rent Rattling the same ring of keys outside a room that has been empty for months.
a merchant who was sold his own warehouse Holding a deed in each hand, comparing the two signatures.
a museum director with an empty plinth A velvet rope around nothing, and a small printed card explaining it.
a schoolteacher whose exam they sold Marking papers that are all, suspiciously, perfect.
a tailor holding an unpaid bill and half a coat The coat has one sleeve. It waits on a dummy in the window.

Old partners 12

a driver never told the job was off Waited at the corner until the horse fell asleep.
a fence still holding their unsold goods A shelf with their name on it and a storage bill that grows weekly.
a first partner who went honest and wants company Wearing an apron, holding out a second apron.
a former partner who wants their half Half of everything in the drawing could be chalked with a dividing line.
a former pupil, now working for the other side Always one step ahead, leaving doors open as a greeting.
a lookout left waiting on a roof all night Still stiff in one shoulder. Carries a cushion now.
a rival who cannot retire until they do Two old thieves on two park benches, each watching the other's bag.
a twin who keeps being arrested in their place Same face, far worse luck, sitting in a cell with a packed lunch.
the crew they walked out on mid-plan Four silhouettes on a rooftop, one gap in the line.
the forger whose best work they signed An artist's pride, wounded. Ink-stained fingers drumming a table.
the partner they taught everything but the ending Stuck halfway through a trick for ten years, cards still in hand.
the teacher who said they would amount to nothing Turns up at every success with a notebook, grudgingly ticking boxes.

People who want something else 12

a biographer who needs the last chapter A thick manuscript and a pencil behind each ear.
a child who believes they are a hero Wearing a paper mask copied from the wanted notice.
a lawyer carrying an inheritance A briefcase chained to the wrist and a very tired pair of shoes.
a locksmith who wants to know how Not angry, only curious. Carries the beaten lock in a paper bag.
a long-lost sibling with a photograph Holding the photo up beside every stranger of the right height.
a mapmaker who needs a way into a walled garden A map with one blank square and a hopeful arrow.
a newspaper artist paid by the sketch Draws them from other people's memories: a chin, a hat, a way of standing.
a painter who wants them to sit for a portrait Easel folded under one arm, turpentine rag in the pocket.
a playwright who put them in a comedy Following at a distance to check the costume is right.
a rich recluse with one impossible job Seen only as a gloved hand passing an envelope through a gate.
an inventor who needs a lock tested Drags a door behind them on a handcart.
an old mark who wants to hire them The one person who has seen the work from the receiving end.

Stranger pursuers 12

a cat that expects feeding at midnight Sitting on the sill of whatever room they are in, every night.
a debt that changes hands every month A slip of paper passed down a long line of strangers.
a ghost story the town tells about them Children at a window, pointing. The story has added a cape.
a hound from an old job, whiskers gone white White round the muzzle, tail going, three towns from home.
a parrot that learned their real name It says it clearly, in crowds, at the worst moments.
a pigeon with a letter addressed only to them It has landed on their hat mid-disguise.
a reputation larger than they are A giant shadow on a wall and a small figure at the foot of it.
a small brass band that plays when they arrive Nobody ordered it. The tuba player waves.
a statue the town put up to thank the wrong person The bronze face is theirs. The name on the base is not.
a story that grows each time it is told Two gossips at a pump, hands held wider and wider apart.
a town clock that strikes when they pass Only superstition. Draw them hurrying under it with their collar up.
their own wanted poster, badly drawn It follows them from wall to wall and looks less like them each time.

How this list was compiled: Original list written for Draw This Next, September 2026. Each pursuer is a person or a thing with a reason, and none of them means the rogue physical harm: the chase is a matter of patience, paperwork, pride or affection. The notes on what to draw are our own suggestions. Licence: own work

One rule: all 60 rules

Who they will not take from 12

never takes from a house where someone is unwell A light burning late upstairs and soft steps going the other way.
never takes from a house with a cradle Passing a window, hat lifted to nobody, moving on.
never takes from a shop with one candle lit One small flame in a dark window and a figure turning away.

Show all 60 rules (57 more)

Who they will not take from, continued

never takes from a street they have slept on A chalk mark on a street corner that only they understand.
never takes from a table set for one A single plate, a single chair, and a door closing softly.
never takes from a teacher A stack of unmarked homework, guarded by habit.
never takes from anyone who said good morning Returning a greeting with visible regret.
never takes from anyone who works nights A baker, a porter and a nurse walk through the scene untouched.
never takes from anyone with less than they have Counting their own coins first, then deciding.
never takes from musicians or cooks A fiddle case left open and full in the middle of an empty street.
never takes from the same person twice A notebook of names, each with one neat tick.
never takes from the town they were born in At home their hands stay in their pockets. Draw the pockets bulging with fists.

What they will not take 12

never reads a letter they carry Envelope held seal outward, eyes on the ceiling.
never takes a child's toy A wooden horse wound up and left running in the hallway.
never takes a pet, however willing Gently unhooking a kitten from their coat at the gate.
never takes a thing somebody talks to A worn toy rabbit left on a shelf of silver.
never takes a tool someone earns with A cobbler's hammer set carefully back on its bench.
never takes a wedding ring Every other ring from the tray is gone. One sits alone on the velvet.
never takes anything with a name sewn in Turning a collar to read the label before deciding.
never takes medicine, bread or boots Three things stepped round on the way to the strongbox.
never takes more than fits in one pocket The pocket is enormous and specially made, but it is still one pocket.
never takes the last of anything One apple left in a bowl, with a gap all round it.
never takes the only copy Copying a page out by candle before leaving the book behind.
never takes what they could simply ask for Knocking, hat in hand, to the owner's great confusion.

How they work 12

always knocks first, in case Knuckles raised at a door they already have the key to.
always leaves by the front door Hat on, door held open for themselves, a nod to the street.
always leaves one coin A single coin stood on its edge where the purse was.
always locks up after themselves Testing the handle twice from outside, like a careful shopkeeper.
always pays for what they eat on the job Coins stacked beside an empty pie dish.
always wipes their feet A doormat with two clean prints, facing in.
never breaks what a key would open Waiting a week for a copy before touching a window pane.
never lies to a partner Saying something unwelcome, mid-job, with complete calm.
never runs: walks, and tips their hat Strolling past a shouting crowd at an even pace.
never wears the same disguise twice A bonfire of false beards behind the last town.
never works on a night bright enough to read by A calendar with thirteen circles and a line through each.
works alone or not at all A table laid for a crew and one chair pulled out.

Once it is done 12

always returns it if asked nicely Handing a bracelet back across a tea table with a small bow.
always tells one person the truth A different listener in every town: a barber, a ticket seller, a child.
buys back anything that made someone cry At a pawn counter, paying double for their own takings.
feeds the dog before leaving A bowl set down in a dark hall, and a tail thumping.
gives the best piece away the same night A stranger on a bridge looking down at a brooch in their palm.
leaves the windows cleaner than they found them A rag in the back pocket and one pane that shines.
never counts it until morning Asleep with the bag unopened as a pillow.
never keeps a thing longer than a year A shelf of labels with dates and nothing on it.
never spends it in the town it came from Walking out past the last house with a full bag and an empty stomach.
replaces what they took with something handmade A carved wooden bird sitting where the gold one stood.
sends a tenth to the place they grew up A parcel tied with string and a postmark from somewhere small.
writes a thank-you note, unsigned Good paper, good hand, pinned where the painting hung.

Superstitions 12

always carries the first coin they ever took Worn smooth, on a cord round the neck, never spent.
always greets a crow by name Hat raised to a rooftop. The crow does not reply.
always touches the doorframe on the way out A dark thumb-shaped patch at shoulder height on every frame they have used.
always turns their coat inside out for luck The lining is brighter than the outside and covered in pockets.
always wears one odd sock Shown at the ankle when climbing: one striped, one plain.
never crosses a threshold left foot first A little hop at every doorway, even at speed.
never says the plan out loud twice One finger raised to stop a partner mid-question.
never starts a job on a Friday A week planner with one column filled in by doodles.
never takes anything numbered thirteen A row of deposit boxes with one left carefully shut.
never whistles indoors on a job Lips pursed, then caught and pressed shut.
never works a street with three black cats Counting cats from a corner. Two so far, and something moving on a wall.
never works on their own birthday A small cake with one candle, eaten on a rooftop.

How this list was compiled: Original list written for Draw This Next, September 2026. A thief's rule is the kindest thing about them, so each entry is a limit they set on themselves. The notes say where the rule shows in a drawing and are our own suggestions. Licence: own work

How it works

This rogue backstory generator deals a thief's past in six parts: a first theft, a teacher, a line of work, the job that went wrong, a pursuer and the one rule they keep. It is text only, and nobody gets hurt.

Read the full guide

Start from the rule

Rogues in stories are liked for their limits. The last part of every result is a rule, such as never takes the last of anything, and it says more about the face than the crime does. Draw the rule first: a hand that stops, a coin left on a sill.

A criminal past that stays light

As a criminal backstory generator it keeps to locks, paper, talk and night cargo, with no weapons and no gangs. Every failed job ends in embarrassment, never injury. Read the pursuer beside the failed job and you have a chase to draw.

Draw the teacher and the rogue together. A rogue copies somebody's hands, hat or walk.
The first theft sets an age. Draw them at that size once, holding the thing they took.
Running a tabletop game? Print 30 and let each player trade one part with the player beside them.

Questions and answers

What makes a good rogue backstory?

A reason, a teacher and a limit. This page deals six short parts and ends on a rule the character will not break. A thief with one line they refuse to cross is easier to like and easier to draw.

Does it follow the rules of a tabletop game?

No. Rogue here is the plain English word for a likeable thief. The lists name no game, rule book, setting or spell, so a result fits any world, from a walled fantasy port to a modern city.

Is anything violent in the lists?

No. All six lists were written without weapons, injury or cruelty. The worst that happens in a failed job is a friendly dog, a wrong address or a long walk home with an empty bag.