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, 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, 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 way to really understand foundation, to understand shapes and make your cartoon solid" is to master the fundamentals.
It's a reminder that even legends are still learning.
The Panic That Powers Creation
What drove Ann to political cartooning? Two specific moments: watching the Tiananmen Square massacre in 1989 while working on a freelance gag cartoon project, and then the Anita Hill/Clarence Thomas hearings.
The Anita Hill hearings particularly enraged her because "I was a young woman who had worked, and I had dealt with sexual harassment, and I knew all this crap that these senators were arguing about... They knew absolutely nothing about the reality of sexual harassment for women."
These moments awakened something in her: "I finally took my love of art and drawing and combined it with something, and it really clicked for me." Sometimes you need to get angry enough to find your voice.
The Mission-Driven Gender Gap
Ann has a fascinating theory about women cartoonists. There were maybe 17 or 18 working women cartoonists during the suffrage movement. "But once they got the vote, they all quit." The pattern suggests women cartoonists are driven by a mission: "We have a mission, right? We have other things, but we have to do this."
It's a different relationship to the work, less about career, more about necessity. When there's injustice to fight, women pick up their pens. When the immediate battle is won, they move on to other ways of making change.
The Real Housewives Administration
Our conversation kept coming back to the Trump-Musk fallout, and Ann captured it perfectly: "It's like watching Real Housewives except there are real-world consequences." These aren't just personality conflicts – they're affecting international relations, democracy, society, and the entire government.
The fact that two of the most powerful people on the planet are conducting their beef online makes it even more surreal. As I pointed out, "It's also performative. It's not like they're doing this in person." The online disinhibition effect is amplifying everything to a level that's "affecting our international reputation."
Why We Can't Check Out Now
Despite the exhaustion, Ann's message is clear: this isn't the time to tune out. "I had a lot of friends who just basically checked out of the news because they're tired... But I don't think now is the time to do that."
Her practical advice: "You can listen to the radio news while you're getting ready in the morning. Just keep updated on things because this administration is throwing things faster than anyone can even process them."
And then do something about it: "Call your representatives, go join a protest, make some noise because that's the only thing that's going to help us."
The Historical Echo Chamber
Our conversation got darkest when Ann talked about her German relatives and how she's always wondered how educated, normal people got "sucked into something like a Nazi government, a Hitler regime." Her conclusion is chilling: "I see it now."
"We have a guy in office right now who is definitely playing... to people's fears. Autocrats do that in order to get power and keep it." It's not hyperbole when you're watching the playbook get executed in real time.
Cartoonists’ Response to Chaos
What struck me most about talking to Ann is how cartoonists process chaos differently. We don't just report on it – we distil it, exaggerate it, make it impossible to ignore. When democracy is under siege, political cartoonists become war correspondents armed with brushes instead of cameras.
Her work during the Bush administration, particularly her devastating takedowns of Dick Cheney, remains some of the most prescient political commentary of that era. But as she noted, "now is a more frantic time with Trump and more urgent."
The question is: how do you capture the surreal when reality itself has become a cartoon?
Drawing Through the Apocalypse
As we wrapped up our chat, I was struck by Ann's combination of clear-eyed realism and stubborn optimism. Yes, we're watching democracy get stress-tested by megalomaniacs. Yes, it's terrifying. But we're also watching artists, journalists, and citizens refuse to normalise the abnormal.
Ann's still at her kitchen counter, still going to life drawing classes. She's documenting the decline while fighting against it, one cartoon at a time.
In times like these, maybe that's exactly what heroism looks like: showing up every day and drawing the truth, even when –especially when– it's too absurd to believe.
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Thanks for tuning in!
‘til next time,Your pal,
Key Resources Discussed:
* Democracy Under Siege - The prescient documentary featuring Ann
* Columbia Journalism Review article on Pat Oliphant - Ann's piece on the legendary cartoonist's drawing process
* "Curtis Yarvin's Plot Against America" in New York Magazine - Essential reading on the neo-reactionary movement
* The New Yorker piece on Jeff Bezos and the Washington Post - Required reading on media ownership and democracy
