10/08/2026
Over the last three decades, has starred in more than 60 films, won two Oscars, and cemented himself as one of the defining figures in pop culture.
He’s coming off two and a half years of continuous work—the longest stretch of his career. Now, with every role he takes, he wants to do something he’s never done before.
On a gloomy day in Los Angeles, Pitt reflects on legacy, loss, ambition, and more.
To read the full story of this Esquire exclusive, visit esquireme.com
Story by Ryan D’Agostino Ryan D’Agostino
Photographed by Chantal Anderson Chantal Anderson
Styled by George Cortina georgecortina
Hair by Jason Low mister jasonlow
Make Up by Jean Black
Production by Hyperion Hyperion
Set Design by Peter Gueracague Peter Gueracague
Tailoring by Susanna Badalyan
16mm by Luke Hanlein luke hanlein
Special Thanks to The Garibaldina Society, LA. The Garibaldina Society
Esquire Executive Creative Director: Nick Sullivan Nick Sullivan
Esquire Executive Director: Martin Hoops Martin Hoops
Esquire Visual Director: James Morris James Alexander Morris
Esquire Entertainment Director: Andrea Cuttler Andrea Cuttler
