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Welcome to the CartoonStock Blog

Here you’ll find insights from Bob Mankoff, former New Yorker Cartoon Editor, educational resources to help you use humor, our very own Cartoon Caption Contest, and plenty of cartoons. Sign up for cartoons & offers straight to your inbox and never miss a laugh!


Expert Guides & Insights

Cartoon History

The Highest Price Ever Paid for a Single Panel Cartoon

Learn More About The History of Cartoons

Psychology Behind the Humor

Cartoon by Andrew Toos. During a board meeting the lead is asking why his humor is not apprieciated

What Makes Cartoons Funny

View all Posts

Have Something Specific in Mind?

Cartoon by Ron McGeary

How to Add Humor to Tech Presentations Using Cartoons

Find Cartoons for Your Industry


Special Features



Bob’s Cartoon Lounge

Death by Powerpoint

How to Avoid Death by Powerpoint

View All of Bob Mankoff's Hilarious Insights

Caption Contest Commentary

“No Rest for the Wicked” Caption Contest Commentary with Lawrence Wood

View Previous Competitions

Anatomy of a Cartoon

Anatomy of a Cartoon: Grandparents

More From Phil Witte and Rex Hesner


Caption Contest

CartoonStock Caption Contest

The New Cash-Prize Caption Contest.

So you think you're funny? We do, too!! Each month we're offering a cash prize of $1,000, $500 to first place and 5 runners-up prizes of $100 each. What's the catch, you ask? Well, you have to pay $5 to play. But with a chance at up to 500 smackeroos, it's well worth it!


ENTER NOW

View previous winners

Recent Posts

Cartoon by Rosie Brooks

How Cartoons Can Make Marketing Content More Engaging

September 8, 2025 by CartoonStock

  Marketing feels like shouting into the void sometimes. You craft the perfect campaign, hit publish, and… crickets. But here’s the thing: your audience isn’t ignoring you because your message is wrong. They’re scrolling past because it looks like everything else they’ve seen a hundred times today. That’s where cartoons in marketing content come in….
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Cartoon by Dave Allen

Using Cartoons in Tech: How to Simplify, Humanize, and Supercharge Your Content

August 28, 2025 by CartoonStock

When most people think about tech content, cartoons probably aren’t the first thing that comes to mind. But maybe they should be. Here’s the thing: technical content often gets buried under its own complexity. Sure, it’s packed with valuable information, but if your audience can’t easily digest it, what’s the point? Whether you’re explaining a…
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“Pirates” Caption Contest Commentary with Lawrence Wood

August 25, 2025 by Lawrence Wood

Last month’s contest featured a drawing by New Yorker cartoonist Meredith Southard. It’s set on a pirate ship where the captain, who’s wearing an eye patch and has a hook for a left hand, is saying something to the pirate who’s standing to his right. The captain’s speaking out of the side of his mouth,…
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Cartoon by John Carter

Cartoons in Tech Marketing: What Works and What Doesn’t

August 25, 2025 by CartoonStock

Cartoons in tech marketing are no longer just a novelty. They’re a powerful tool for cutting through complexity, building audience rapport, and helping your brand stand out in an industry saturated with buzzwords and bullet points. But for every cartoon that hits the mark, there’s another that falls flat—or worse, undermines the message entirely. So…
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Cartoon by Jerry King

Using Cartoons for Tech Startups: A Creative Way to Stand Out

August 19, 2025 by CartoonStock

In a world where startups are competing for attention—and often pitching complex, abstract ideas—cartoons offer a refreshing edge. They’re human, clever, and surprisingly effective at simplifying big ideas. This article explores how tech startups use cartoons in real-world ways to explain, differentiate, and connect. Read the full guide: Using Cartoons in Tech: How to Simplify,…
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Cartoon by Aaron Bacall

How Tech Companies Can Use Cartoons Without Legal Issues

August 14, 2025 by CartoonStock

Tech companies are constantly looking for ways to stand out, whether in a pitch deck, a blog post, or a social media campaign. Cartoons are a powerful way to add personality and humor to technical content, but many teams don’t realize that using them comes with legal responsibilities. In this article, we’ll break down what…
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