Caricatures: Then & Now

This collection traces my work with caricature from the early 1990s through today. The first section features hand-crafted illustrations created using traditional and digital techniques. The second revisits one of those visual styles through an iterative collaboration with ChatGPT’s image generator (powered by DALL·E), illustrating how the role of the illustrator has evolved from placing every mark to directing, refining, and evaluating the results.

Samuel Beckett

Bill Clinton

Bob Dole

Frederick Douglass

Michael Moore

Richard Nixon

Ruth Bader Ginsburg

George Washington

Revisiting Caricature

More than thirty years after drawing the Joe DiMaggio caricature below, I wondered how closely AI could capture its stippled aesthetic. Working iteratively with ChatGPT’s image generator (powered by OpenAI's DALL·E), I refined each portrait through repeated prompting and critique, using the original illustration as the visual benchmark.