Caption Writing Tips

10 Caption Contest Tips for Winning

Crafting a funny caption is both an art and a science. Whether you’re entering a caption contest or just want to entertain your friends, the right mix of wit, brevity, and creativity can make your words shine [and win]. Use these ten actionable tips on your next contest entry!

1. Analyze the Photo Carefully

Before you write, take a moment to absorb the image. Who are the characters? What’s the setting? Is there something unexpected or absurd? Focus on the element that stands out.

Lawrence Wood, a New Yorker Caption Contest veteran, advises looking for “the logical tension—what’s just a little bit off in the scene?” This sharpens your focus on what’s ripe for humor.

Example: In a cartoon showing a snail at a finish line, the obvious theme is slowness, but a closer look might reveal the snail has a cheering crowd. This opens up new angles, such as competition or fame.

2. Think in Opposites

Humor often lies in the unexpected. Try flipping the usual perspective or exaggerating contrasts.

Example: A photo of a cat sitting in a doghouse.

Caption: “Well, one of us needs therapy, and it’s not me.”

3. Use Brevity for Impact

The best captions are short and punchy. Trim the fat from your punchline Aim for 10-12 words max.

Example: A picture of two penguins wearing sunglasses.

Caption: “Cooler than icebergs.”

4. Tap Into Relatable Humor

Think about universal experiences or emotions the image evokes. Relatable captions often land well because they connect with a wide audience.

5. Embrace Absurdity

Sometimes the most nonsensical caption is the funniest. Embrace randomness if it fits the image.

Example: A giraffe peering through a car window.

Caption: “Just checking if you’ve seen my neck pillow.”

6. Channel a Character’s Voice

Imagine the thoughts or dialogue of the characters in the image. Anthropomorphism—attributing human traits to animals or objects—works especially well.

7. Play With Puns… Sparingly

A good pun can elicit a groan-laugh, but overuse can be cringeworthy. Keep them clever and original.

Example: A bee holding a microphone.

Caption: “To bee or not to bee? That’s my opening joke.”

8. Consider Cultural References

Pop culture, idioms, or current events can add a layer of depth. Just be sure the reference is widely recognizable.

9. Revisit and Refine

The first draft of your caption isn’t always the best. Experiment with different phrasings or angles. As Lawrence Wood says, “Editing is where the magic happens.”

10. Trust Your Instincts

If it makes you laugh, you’re onto something. Trust your comedic intuition and have fun with the process. After all, humor is subjective—not everyone needs to get the joke for it to be great.

Now that you’ve mastered these tips, it’s time to put your skills to the test. Submit your funniest take on the current featured image. You might just see your words in the spotlight—and who knows, you could win a prize!

Happy captioning!