Famous Caption Contests & What We Can Learn

Caption contests have been around for decades, from magazine competitions to viral internet memes. Some of the most legendary contests have produced captions that are witty, sharp, and unforgettable. Let’s take a look at some of the most famous caption contests and the lessons they teach us about writing winning captions.

1. The New Yorker Cartoon Caption Contest

📖 The Gold Standard of Caption Contests

The New Yorker magazine has been running its weekly cartoon caption contest since 1999. With thousands of entries per week, it has produced some of the most clever and refined captions in history.

What We Can Learn:

✅ Subtlety Works – The best captions aren’t always the loudest or most obvious. They let the reader connect the dots.
✅ Situational Humor is Key – Winning captions often highlight the absurdity of the situation in the cartoon rather than forcing a joke.
✅ Conciseness Matters – The best captions rarely exceed 10 words.

💡 Example Winning Caption:
Cartoon: A man and a bear sitting at a bar.
Winning Caption: “I’ll have what he’s having.”

2. The New York Times’ “Best Picture Caption Contest”

📸 A Play on Pop Culture

The New York Times runs an annual caption contest for Oscar-nominated films, inviting readers to add humorous captions to iconic scenes.

What We Can Learn:

✅ Pop Culture References Work – A well-placed reference to movies, politics, or viral trends can make a caption feel fresh.
✅ Exaggeration is Funny – Sometimes, taking an emotion or situation to the extreme makes a caption hilarious.

💡 Example Caption for an Image from “Titanic”
“When you say ‘unsinkable,’ do you mean emotionally?”

3. The Reddit “Photoshop Battles” & Meme Contests

🌍 The Internet’s Wild West of Captions

Reddit’s r/PhotoshopBattles and Twitter’s viral meme contests take captioning to a new level by remixing images with hilarious text overlays. These contests are less about polished humor and more about fast, reaction-based comedy.

What We Can Learn:

✅ Relatability Wins – The best captions make people think, “That’s SO me!”
✅ Timing is Everything – A joke can lose its impact if it takes too long to set up.

💡 Example Caption on a Photo of a Dog in a Suit:
“When your job interview is at 9 but belly rubs are at 10.”

Final Takeaways:

• Test different humor styles—dry wit, absurdity, or pop culture references.
• Keep it concise—brevity makes a caption hit harder.
• Think outside the box—unexpected angles often win.

Want to test your skills? Enter our latest caption contest and see if you can craft the next legendary caption!