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The Cartoonist's Paradox: Easy to Start, Hard to Retire - The Art of Connection with Kevin "KAL" Kallaugher

DMA#27: An Hour of Cross-Cultural Cartooning: How KAL Mastered British and American Political Humor with nearly 50 years at the drawing board.
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Draw Me Anything: A Conversation with KAL (Kevin "KAL" Kallaugher)

I sat down with legendary editorial cartoonist Kevin "Kal" Kallaugher for an engaging hour-long conversation that blended insights into the craft of cartooning with live drawing demonstrations. The discussion covered KAL's remarkable 50-year career trajectory and the evolving landscape of editorial cartooning.


Learn more about KAL’s background in the post below:

Don't forget! DMA#27 Live Tuesday @ 12pm with Special Guest Kevin "KAL" Kallaugher

Don't forget! DMA#27 Live Tuesday @ 12pm with Special Guest Kevin "KAL" Kallaugher

That’s right, Tuesday at 12pm Eastern, I’ll be drawing and speaking with cartoonist and good pal, Kevin KAL Kallaugher


KAL is approaching his 50th anniversary with The Economist in 2028, having also spent 31 years at the Baltimore Sun. The conversation explored how editorial cartoonists, unlike many other professions, tend to stay in positions for decades, becoming "part of the furniture" of daily journalism, until recently...

A Rough Guide to Hell

He discussed the importance of "batting average" over being a "home run hitter" in editorial cartooning. "The hard part is retiring as a cartoonist because then you have to do 10,000 original cartoons," adding that “Consistency matters more than occasional brilliant pieces.”

KAL emphasised creating "effective cartoons" that connect with readers, regardless of whether they agree with the viewpoint. The goal is engagement rather than universal approval, especially when working for publications like the Baltimore Sun that served diverse readerships across the political spectrum.

We got into the nuts and bolts of cartooning, and how timing on the page works a lot like timing on stage. KAL described how a composition can lead your eye right to that “aha moment,” the little spark where the joke lands and suddenly you’re in on it with him. He also talked about being the new guy back in the late ’70s, the first cartoonist at a magazine that he described as “grey and turgid” (which sounds less like a publication and more like something you’d need antibiotics for). To prove he belonged, he drew like a man possessed—layering on cross-hatching until the drawings practically shouted, “See? I’m worth the space!” The art had to look hefty enough to muscle its way in among all that serious text.

Because he’s lived and worked on both sides of the Atlantic, KAL has this rare double-vision: part London pub, part Washington think tank. He joked about the whiplash of trying to land a gag that makes sense to Brits and Americans; two audiences separated by a common language with wildly different cultural shorthand. A dartboard in a pub? Every Brit gets it instantly. Show that same cartoon to an American, and half of them wonder why you’re suddenly talking about bugs. That balancing act, weaving in Britishisms while tackling global politics, makes his cartoons feel like cultural exchange programs with a punchline.

We talked about how cartoons often get brushed off as “just entertainment.” They’re not. Visual satire has teeth; it always has. Think of Thomas Nast taking down political machines, or cartoonists today who risk their lives just for drawing the truth. The real power of cartoons is that anyone can understand them. You don’t need a degree or even to read a single word. One image can cut straight through.

The second half of our chat featured both of us sketching while talking, with one drawing request of a "MAGA pigeon at an anti-Trump demonstration". We also talked about:


KAL has been at this for nearly fifty years, and what’s remarkable isn’t just the sheer volume of work—it’s the consistency, the global perspective, and the technical chops that make him the benchmark for editorial cartooning. He’s built a career on connection, discipline, and genuine care, and watching him work feels like a masterclass in how to say something big with just a few lines.

And then came the live drawing. No matter how long you’ve been in the game, the joy of putting pen to paper, of chasing that spark of something new, turns out to be the real secret ingredient. That’s what keeps cartooning alive.

Thanks for watching!
‘til next time

Your pal,


Connect with KAL

Follow KAL's Work:

https://shop.kaltoons.com/

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