Jessica Helfand|The Icarus Diaries
March 10, 2026
08: Featherweight
Read the introduction to this series.

60 x 48 inches
Oil and wax on canvas
2026
Recently I have been thinking of Icarus as a kind of footsoldier, out scavenging in an open field. Acquiring his arsenal. Gathering materials, and weighing his options. (Weighing his fate.)
The idea of painting him in a flight suit seems right—adventurer as aviator—and I think there will be another version at some point where the flight suit becomes a straitjacket. That line between freedom and failure seems tenuous.
For now, he’s a farm boy. His posture is frontal, solid and stolid, both. There’s a touch of Grant Wood in this exploration, not intentional though I’m aware of it. If I am going to root out the Icarus-ness of this story, some of the source material will nod to other things, and that includes (canonical things by) other artists.
Kiki Smith once described painting animals (and, I’m guessing, their splintered remnants) as a combination of geometry and consciousness. This feels right.

AI is like a Ouija board, leading me to a wide, and sometimes random range of components—nineteenth century noses, eighteenth century poses— a loony mashup of crowdsourcing, bricolage, and happenstance. Just as research is more rewarding when I let myself explore the adjacencies, I am taken by the surprising, oblique references that surface along the way. They’re random, yet organic; related, but raw; weird, wonderful, often disastrously wrong and other times, just extraordinary.
It’s never about a prompt. It’s always about dumpster-diving through the wreckage. If this story has the resonance I think it does, the references can (should, actually) be more eclectic, not less. AI doesn’t know what it doesn’t know—neoclassical features, nineteenth century settings, feathers, footsoldiers—I’m not sure it matters.
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By Jessica Helfand
Jessica Helfand is an artist and writer based in New England. A former critic at Yale School of Art and one of the founding editors of Design Observer, she is the author of several books on visual culture including Self Reliance, Design: The Invention of Desire, and Face: A Visual Odyssey.