Free Story Friday: The Crooked Man – A Terrifying Urban Legend Reimagined

Free Story Friday: The Crooked Man

There was something off about the picture.

I’ve seen every kind of classroom doodle—hearts with initials, superheroes with impossible muscles, stick families under bright yellow suns. This wasn’t that. This was careful. Intentional. Like the artist wanted to make sure the thing in his head arrived exactly as it looked.

Caleb Henderson sat hunched over his desk, shoulders curled like a question mark. His pencil moved in quick, sure strokes, pausing only so he could rub a thumb across the page to blur a shadow. The rest of the class worked through their spelling sheets, pencils tapping in uneven rhythms, chairs creaking, the room a soft, familiar hum. Caleb’s silence felt different—thicker somehow, the kind that collects in a room and waits.

“Caleb,” I said, keeping my voice even as I walked the row. “Spelling first, okay?”

He didn’t look up. From my angle, I could see the figure—if you could call it that. Tall as the page would allow, legs bowed, one knee bent the wrong way. Arms dangled past the knees, hands with too many long fingers. The head was too large, the mouth a black gash of a grin, eyes two deep pits.

“Let me see,” I said, holding out my hand.

He slid the paper toward me but kept his gaze on my face. His voice came small and steady. “If you keep it, he might come for you instead.”

The hairs along my arms prickled. Two desks over, Maya’s pencil stilled. She mouthed something to Jacob—four quick words in a cadence I almost recognized—then Jacob shook his head hard enough to make his hair flop over his eyes and bent back to his worksheet.

“And who is he?” I asked, aiming for light.

Caleb’s mouth trembled. “The Crooked Man,” he whispered. “He comes every night. He wants to come inside.”

I folded the paper once and slid it beneath a stack of worksheets. “Spelling first,” I said again. “Then—if there’s time—you can draw at the end.”

He stared at me like a much older person might, like he was measuring whether I understood something and had failed. Then he bent over his work and printed each list word perfectly, one letter at a time.

The morning went on. The bell ran its course. The hum of routine should have settled me. But my eyes kept drifting to the folded paper under the worksheets, as if it called across the desk to be noticed.

At lunch, I went to the teachers’ lounge, poured burnt coffee into a mug with a chip in the rim, and set the paper down. When I opened it, I wished I hadn’t done it alone.

The crooked house was as wrong as he was—roofline sagging, windows mismatched, door too narrow. The man’s half-turn made him seem both still and moving. Close up, the grin was more a tear in the face, edges smudged like a wound.

“Whoa.” Angela from third grade leaned in, tray balanced on her hip. “Did a kid draw that?”

“Caleb,” I said. “He’s… talented.”

“That rhyme,” she said. “My lola used to say it was bad luck to say the Crooked Man one three times. The older kids at recess will whisper it to scare each other.” She lowered her voice and, without finishing it, sang the first line under her breath. “There was a crooked man…”

I smiled like it was nothing and folded the paper again. The smile didn’t stick.

At recess I took yard duty. The second-graders jump-roped in a circle, song sliding over asphalt. Not the Crooked Man rhyme—something about lemonade and a lost shoe—but when Maya tripped and the rope skittered away, two of the boys began a whispering chant, sing-song and low. There was a crooked man… I stepped closer and the boys stopped, eyes wide and guilty. “We’re not supposed to,” one of them said. “My brother said if you say it all the way, he hears you.”

After school, I tucked the drawing into my bag, sandwiched between lesson plans. I meant to leave it in the file cabinet. I walked out with it anyway.

At home, my little house on Pine Street felt unusually still. I set the drawing on the kitchen counter and poured a glass of wine I didn’t finish. The folded paper sat there like a guest I hadn’t invited.

I told myself I’d toss it in the morning.

Sometime after two, I woke to the kind of silence that has weight. The house was dark except for the honeyed glow of the streetlamp leaching in through the blinds.

I slid from the bed and went to the window. I parted two slats with two fingers.

He stood at the edge of the light, just where the darkness begins. Too tall. Too thin in places and too wide in others. The head tipped too far to one side like a bird listening. One shoulder higher than the other.

The sodium light turned the world to cardboard, but the edges of him refused it. I blinked—and he was gone.

I stared until the honey light turned gray with morning. When I went to make coffee, the drawing was on the counter as I’d left it. I opened it with the clumsy hands of a person who already knows what she will see.

The crooked man stood closer to the house now, shoulder grazing the crooked eave. In one of the windows a faint figure had appeared—a stick figure small and careful, unlike the rest. No face, just the suggestion of a head turned to the glass.

It looked like Caleb.

I called the Hendersons. His mother answered on the second ring. “He’s fine,” she said before I got out anything more than my name. “He gets ideas. We ignore the ideas.”

“Has he said anything about someone at your house? A man—”

“My husband would have told me,” she said. “We’re on top of it. Thank you.” She hung up.

That afternoon, after the last bus coughed out of the parking lot, I found Maya and Jacob by the coat hooks whispering, heads together. They sprang apart when they saw me, and Maya’s cheeks blotched pink.

“Everything okay?” I asked.

Jacob bit his lip. “It’s just—Caleb said—”

Maya shot him a look. “We don’t talk about it.”

“Whose rule?” I said gently.

“Everyone’s,” Maya said. And then, to me, like a warning for a grown-up who didn’t know the playground rules: “If you look at him too long, you forget which way straight is.”

That night, the bathroom mirror curved at the edges like water held flat only until someone breathes over it. My reflection lagged a half-second when I turned my head. When I reached up to touch my cheek in the glass, my mirrored hand reached slower, like it had farther to go. I laughed—small, breathless—and blamed the old house.

I went to bed and dreamed of the hallway. In the dream, the length kept changing, long and short, long and short, and when I tried to reach the door at the end, it bent away like a ruler snapped in two. Footsteps followed me, uneven, a drag in them. A voice threaded through my own breathing, chanting in that cadence childhood rhymes live in forever.

There was a crooked man…

I woke with my heart flapping and a metallic taste behind my tongue. The clock read 3:03. I sat in the kitchen with the lights on until the world grew edges again.

Thursday morning, Caleb’s seat stayed empty. The principal met me at my door.

“He didn’t come home last night,” she said. “Parents called the police. They’re searching.”

On my desk, under the grammar workbooks I could have sworn I’d left on the shelf, sat the drawing. I hadn’t brought it to school.

The crooked man stood at the door of the crooked house now, one hand laid on the frame. In the window, the figure had sharpened. I could see the hair in a bun and the faint outline of glasses.

Me.

I took the paper by the corner and tried to tear it. The fibers held like it had been lacquered. When I looked away and glanced back, the tear was gone.

After dismissal I drove to Cedar Court, where the Hendersons’ ranch house sat at the end of a cul-de-sac. A tricycle lay on its side in the yard, one wheel turning when there was no wind.

The woman across the street watered dirt that didn’t need water. She watched me over the hose. “You one of his teachers?”

“Yes,” I said. “Have you seen him? Or anyone near the house?”

She looked at the Hendersons’ drawn blinds. “Police were here till morning. Not the first kid we’ve lost.” She shut off the hose. “Some say a man walks late here. Bent all wrong. If you see him, don’t watch too long. And never let him in.”

At home I propped the drawing on the mantel and sat where I could see it. The sun slid off the edges of things. Somewhere inside the wall a pipe ticked.

At 12:17, three slow knocks sounded at the front door.

I stood, legs trembling. Through the peephole, he filled the circle: one eye too close, the far socket a pit. That smile. The head tipped, listening.

The knocks came again. Then silence.

The latch turned.

The door didn’t open, but footsteps crossed the floor behind me. Uneven, dragging.

“There was a crooked man…” The voice slid through the air.

My heel caught on something. The drawing lay at my feet. The crooked man was inside now, standing behind the figure with the bun and glasses.

Behind me.

I turned.

The hallway had lengthened. The straight lines of the walls had softened, tilting toward each other as if the house were bending to watch. The picture frames hung at angles no level could fix.

At the far end, a shadow stretched toward me—not away from a light source, but as though pulled by unseen hands. First came the tilt of the head, listening. Then the higher shoulder, the backwards-bent knee, the turned-in foot.

He moved with the patience of something that knew time would never run out.

I stepped back, my bare feet catching on the edge of the rug. My heel landed on the drawing again. On paper, his hand was already lifting toward my shoulder.

The smell hit first—wet cardboard, pennies, the damp rot of a basement left shut for decades.

He stopped in front of me, close enough that his shadow swallowed mine. Long fingers rose, the joints bending with unnatural slowness.

In the drawing, the same penciled hand rose toward the figure of the woman.

“Take me,” I heard myself say. The words came out hoarse, but steady. “Leave the boy. Take me.”

The smile widened—not pleased, just deeper. His hand came down on my shoulder. It was heavy, pressing through skin and bone, as if testing the fit.

The lights in the hallway flickered, stretching into thin threads before snapping back. The walls pressed closer.

In the drawing, the woman’s hand began to rise toward his. Not to push it away. To hold it.

The floor tilted under me, and the house exhaled—a long, slow breath that made the hair at my nape lift.

He leaned forward, his mouth near my ear. The whisper was warm and damp. “Come along,” he said, like a father coaxing a child.

The rest of the house seemed to bend toward us, as if listening.

---

The police found my front door open the next morning. The kitchen light still burned.

The drawing lay in the center of the rug. The crooked man stood alone now. The window of the house was empty.

---

At Oakwood Elementary, a new boy joined the class. He didn’t speak, didn’t look up from his desk.

When the bell rang, he walked to the front and handed the teacher a folded sheet of paper.

The crooked man stood outside a different house now.

And in the window… was her.

---

© 2025 Karen Cody. All rights reserved.
This original story was written exclusively for the Urban Legends, Mystery, and Myth blog.
Do not copy, repost, or reproduce without permission.
This tale may appear in a future special collection.

Enjoyed this story? Urban Legends, Mystery, and Myth explores the creepiest corners of folklore—from haunted objects and bloodthirsty creatures to chilling historical mysteries. Also,don't forget to check out last week's Free Story Friday

Want more bite-sized horror? Check out our book series, Urban Legends and Tales of Terror, for reimagined fiction inspired by the legends we cover here.

Because some stories don’t stay buried.