"Unmanned Drone" by Kara Walker, "Last Garment" by Simone Leigh, "Rosie the Riveter by Norman Rockwell", A bathing suit designed by Claire McCardell

"Unmanned Drone" by Kara Walker, "Last Garment" by Simone Leigh, "Rosie the Riveter by Norman Rockwell", A bathing suit designed by Claire McCardell Photo-Illustration by TIME (Source Images: See bottom of page)

We asked 25 art-world insiders to tell us about a work of art or design that reflects where American culture is headed, speaks to the present in a meaningful way, or otherwise evokes this moment in time . Here are their answers.

Untitled (Cowboy) 1995 at an exhibition at the Albertina Museum in Vienna, Austria on April 16, 2026. Joe Klamar—AFP/Getty Images

Untitled (cowboy) by Richard Prince

Selected by Olympia Gayot

Richard Prince’s work captures a distinctly American way of constructing identity—pulled from images we already know and slightly reframed until they feel both familiar and off.…