Two Megalomaniacs Walk Into a Democracy: Ann Telnaes on Cartoons, Chaos, and Why We Can't Look Away
Earlier today, I got to speak with Ann Telnaes (https://substack.com/profile/13005553...) , 2025 Pulitzer Prize winner and one of the most fearless voices in political cartooning. (Also, one of my favourite people in the world.) We discussed the urgent question: “How do you document democracy's slow-motion car crash when two unhinged maniacs are fighting over the steering wheel?”
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Ann doesn't mince words. She never has. When I described Trump and Musk as "a petulant toddler and a drug-addled lunatic lobbing bombs," she laughed and countered with her more accurate assessment: "Male adolescents who have too many toys."
We're not dealing with political disagreements here. We're watching what happens when unlimited power meets unlimited ego, and spoiler alert: it's not that funny.
Cartoonists: The Canaries in Democracy's Coal Mine
Ann has a theory that cartoonists are "the canary in the coal mine of democracies," and honestly, after our conversation, I'm starting to think we might already have one lung full of coal dust. The documentary she's featured in, Democracy Under Siege (https://www.newyorkcartoons.com/p/427...) , was made before everything currently happening actually started happening, yet it predicted pretty much everything we're watching unfold.
As Ann put it, there was urgency during Trump's first presidency, "but nobody noticed because he was so entertaining for the media to cover, because it got eyeballs." The cartoonists, however, "did a fairly good job showing who Trump was in the first one." We had a running start this time, but somehow we're still acting surprised that the leopard is eating faces.
When Free Speech Gets Complicated
Our conversation took a serious turn when we talked about Charlie Hebdo. Ann and I were both in the States when the 2015 murders happened, and like me, she felt that gut punch of "sadness and fear and fury." But here's where it gets interesting – and uncomfortable.
"At first, everybody was all... ‘Je Suis Charlie!’, Free speech! —and everybody was together," Ann recalled. "Then, all of a sudden, at least in this country, there started to be a divide." She strained friendships over defending those cartoons. So did I. "I discovered that I definitely am a free speech absolutist because I don't think you go down that path where you start talking about what you can and cannot draw or say."
Her line in the sand is crystal clear: "You're just not allowed to kill people because you disagree with them." The moment someone justifies murder with "Yeah, but the cartoons…" they've lost the argument immediately.
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The Kitchen Counter Revolution
Here's something that blew my mind: Ann still works at her kitchen counter. This absolute legend, who's been skewering politicians for decades, is creating her masterpieces at the same place most of us eat cereal.
Her style evolved out of pure practicality. When she started, she tried to copy the McNally crosshatching approach that everyone was doing. "I realised I couldn't do those cartoons very fast. And in business, you have to work fast." So she just started doing them in her own style fast, using the brush and ink techniques from her animation background.
Sometimes the best artistic breakthroughs come from just figuring out how to pay the bills.
The Art of Evolving Evil
One thing that fascinates me about Ann's work is how her caricatures evolve. She doesn't just create one version of Dick Cheney and repeat it forever. "For me, a caricature is more about who a person is inside rather than how they look outside," she explained. "I wouldn't say that my Cheney looks like Cheney, but it certainly feels like Cheney."
This is particularly evident in her Musk cartoons. As I told her, "Your Musk evolved as he devolved." If you did a retrospective of her Musk drawings, it would show this terrifying de-evolution from celebrated businessman to... whatever the hell this is. Her recent cartoon of Musk strung out in an alley with needles around him perfectly captured not just his downfall, but the Greek tragedy of watching it happen in real time on our collective screens.
The Pat Oliphant Revelation
Ann shared an incredible story about how Pat Oliphant transformed his art. In the '60s, his style was much more cartoon-y. But when he went to speak at the Corcoran School of Art, he noticed they were teaching life drawing and decided to sit in. That's when his incredible draftsmanship really developed.
Ann's advice? "If you want to learn to draw, go take life drawing classes. I still take them." She goes to open sessions to draw the figure because "the best wa...
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