A jack-o'-lantern is one of the easiest things to draw, because it is built from shapes you already know: three triangles for the eyes and nose, a row of Vs for the teeth, and a few curves for the pumpkin around them. This one takes about five minutes with a marker.
The walkthrough follows Cartooning Club's Halloween pumpkin lesson, shot from above so you can see exactly where each line goes. Draw the face first and the pumpkin second. It is the opposite of how most people start, and it is why the face ends up centred.
What you need
A black marker and a sheet of paper. A fine-tip Sharpie gives the cleanest line, but a pencil works and lets you erase. If you plan to colour it in afterwards, marker paper stops the orange bleeding through.
The order that makes it easy
Eyes, nose, mouth, then the outline. The three triangles set the size of everything else, and the mouth defines the width. Once the face is in, the ridges and stem go above it and the sides curve around it. Draw the outline first and you are guessing where the face will fit.
Where it goes wrong
Eyes at different heights. The most common one. Mark both top points before drawing either triangle.
Teeth too regular. A perfect zigzag looks like a graph. Vary the size of the Vs and leave the outer ones open.
Sides that meet the chin in a point. Tuck each side under the chin with a small overlap instead, so the bottom of the pumpkin stays rounded.
More Halloween drawing
The same shape-first approach works for the rest of the season. Draw a bat from a head and two swept wings, or a ghost from a single flowing outline. If you would rather cut than draw, pumpkin carving uses the same triangle face on the real thing, and painting a pumpkin keeps it for another year.
New to drawing altogether? How to draw covers the pencil grades, the light-line sketching method and basic shading before you start on subjects.