When Donald Trump won the 2024 Presidential election, artist and editor Tod Lippy—like many of his peers on the left—was stunned. But instead of turning inward, he went looking for answers. What followed was an obsessive two-day search for voters who had publicly supported Trump, not on social media but in op-eds, news interviews, and regional press. He found 50 of them. Then, having never painted before, he began painting each one.
The result is My Fellow Americans, a grouping of portraits making its debut this week as a site-specific installation with the Meeting at Independent New York. The portraits are sincere, unsparing, and surprising—not least because of how they’ve changed Lippy himself. What began as an attempt to understand turned into something deeper: a strange kind of communion between the artist and his subjects, a project that feels as emotional as it is political.
Over the course of several months, Lippy painted nearly one portrait a day, immersing himself entirely in the process. He spent much of the winter in Los Angeles completing the series, transforming his days into an intense routine of focused labor and introspection.
As the days went on, Lippy wasn’t just learning how to use acrylic gouache—a flat, fast-drying medium he chose for its accessibility. He was also learning how to see. Studying each face in detail, he found himself connecting to people he had little in common with politically. “I actually ended up really being almost fond of these people,” he said, “despite the fact that I have nothing in common with them politically.”
That connection was forged through the mechanics of portraiture. “When you paint a face, especially when you’re really studying people’s eyes and how they comport themselves, you really get to know them,” he said. “It’s crazy. I didn’t think this was going to happen, but it ended up being the best byproduct of the whole experience.”
ARTnews: You’ve said this all started the day after the election. What happened?
Tod Lippy: I’d done a lot of canvassing during the campaign, and I really thought Kamala would win. When she didn’t, I was completely gobsmacked. The first thing I did that day was delete all my social media—everything but LinkedIn. Then I opened up Google and typed in “Why I voted for Donald Trump.” That search turned into two days of obsessive digging. I found 50 people who had publicly explained their vote, mostly in op-eds or media interviews. I wasn’t looking for specific demographics or geographies—I just grabbed the first 50 I could find.
This wasn’t about building a representative sample.
No, it was purely about access. Some of the people came from op-eds—maybe 20 percent—but most were interviewed by the Times, local papers, or TV news. The group ended up weirdly dispersed across the country. Again, I wasn’t looking for “types.” I just wanted to do this quickly, before I second-guessed myself.
You hadn’t painted before. Why use portraiture as your medium?
I think when you’re in a hyper-polarized time, people on the other side start to become abstractions. Figurative painting felt like a way to push against that—to force myself to see them as people. And painting someone’s face, really studying their eyes, their expression, you get to know them in a way you wouldn’t otherwise. I started to feel a kind of affection for these people, even though politically we’re completely at odds.
How did you choose your materials?
I picked acrylic gouache at random, mostly because it dries quickly and has a flat quality I liked. I didn’t want to deal with oils—too slow, too technical. I went to LA that winter, and while I was there, I painted almost one portrait a day. That was my life—paint, eat, sleep, repeat. It took several months to finish the full series, and over time I got better. The early portraits are a little rough, but the later ones are more refined. I was learning to paint as I went, and it was intense. It wasn’t just about technique—I was also learning how to connect to these people through the act of painting.
Did you ever worry about editorializing, even unconsciously?
All the time. That’s why I tried to be scrupulously faithful to the source photos. No embellishing, no color shifts, no making a point with how they looked. It wasn’t about flattering or mocking them. I’ve always been kind of a mimic—I did a series of drawings for my magazine Esopus, and accuracy was important there too. Same with this. I just wanted to be honest in how I rendered them.
What has the response been like? Especially from Trump supporters?
Mixed, as you’d expect. Some people refused to even walk into the room. Others said, “That looks like my grandmother.” A few Trump voters came by. They were totally fine—we talked. They were atypical Trump supporters, but they liked the show. The work isn’t about celebrating them, but it’s not about villainizing them either. That wouldn’t be interesting.
You’ve worked across a lot of mediums—magazines, music, photography. How does this project fit in?
I’ve always been someone who backs into things. I go to a gallery, see something odd, and think, “That’s interesting.” Then I start photographing it. Then it’s a book. Then it’s a show. Same with this. I didn’t set out to make a painting project. I just had a question, and this was the way to answer it. That’s been true for most of my creative work—music, design, photography. It’s just about making sense of the world through making something.
So, are you an artist?
I don’t know. I do a lot—book design, editing, consulting. I started a new press after my magazine Esopus folded. I make music. I guess I just think the world’s more interesting when I’m creating something from it. That’s how I make sense of things. Not everything has to be a capital-P Project. Sometimes you just have to start.
