Drawing Challenge #20: Caricature

#W2DTogether Challenge #20

Original Run: Sunday, January 25, 2026 – Sunday, February 1, 2026

Hi everyone! 🙂

We just hit 20 weeks in a row of providing you with drawing ideas every single week. That alone is worth celebrating!!! 🥂

We hope this challenge series has helped you get past art block, discover new techniques, and maybe even meet a few new art friends along the way. If you are new here, you can see how we got to this milestone by checking all past challenges here.

Now, let’s get into this week’s theme!

The Challenge

Challenge number 20: Caricature

This week’s challenge is about playfulness and letting go of the rules. A caricature is not about realism or perfect proportions, it is about exaggeration.

The Task: Your task is to draw a caricature of either yourself, someone you know, or a well-known person (celebrity, historical figure, etc.).

Need a “Cheat Code”? If drawing a caricature from scratch feels too difficult, you are allowed to “cheat” for this challenge! You can find an existing caricature made by another artist, study it, and redraw it in your own way. As long as YOU are the one doing the drawing, it counts!

How to Approach It

Identify Key Features: Look for the most recognizable parts of a face: a big smile, unique glasses, or a specific hairstyle, and push them to the extreme.
Focus on Energy: Don’t worry about making it look “pretty.” Focus on capturing the person’s personality through bold lines and exaggerated shapes.
Simplify: You don’t need a million details. Sometimes a few well-placed lines can say more than a fully shaded portrait.

The Rules

Must be YOUR drawing.
Medium: Drawings only (pencil, pen, colored pencils, markers, or digital). No paintings.
No AI art.
Requirement: Share at least one caricature drawing.
All skill levels welcome: Whether you are a caricature pro or trying it for the first time!

Where It All Started

This challenge was originally posted on Reddit. You can visit the original thread to see the fun results—from community members drawing their colleagues for the office whiteboard to creative self-portraits!