Brad Pitt Reflects on Legacy, Loss, and His Next Chapter in Esquire’s 2026 Mavericks of Hollywood Issue

Brad Pitt fronts Esquire US’s 2026 global Mavericks of Hollywood issue in a new cover story photographed by Chantal Anderson.

After more than three decades in Hollywood, over 60 films, and two Academy Awards, Pitt remains one of the most recognizable and influential actors of his generation. Yet his focus is not on repeating past successes. Following two and a half years of continuous work—the longest uninterrupted stretch of his career—he says every new role must take him somewhere he has never gone before.

Set against a gloomy day in Los Angeles, the reflective profile finds Pitt considering the experiences that have shaped him both personally and professionally. He discusses legacy, loss, ambition, aging, and the creative restlessness that continues to drive him.

Rather than treating his remarkable filmography as a finished monument, Pitt appears determined to keep evolving. Recognition and longevity may have secured his place in popular culture, but curiosity—and the challenge of doing something genuinely new—still guides his choices.

Read the complete Brad Pitt cover story at Esquire.

Cover photography: Chantal Anderson for Esquire US.
Story by Ryan D’Agostino @rhdagostino
Photographed by Chantal Anderson @chantalaanderson
Styled by George Cortina @georgecortina
Hair by Jason Low @misterjasonlow
Make Up by Jean Black
Production by Hyperion @hyperion.la
Set Design by Peter Gueracague @peter_gueracague
Tailoring by Susanna Badalyan
16mm by Luke Hanlein @photoflood_
Special Thanks to The Garibaldina Society, LA. @garibaldinasociety
Esquire Executive Creative Director: Nick Sullivan @nicksullivanesq
Esquire Executive Director: Martin Hoops @mhoopsdesign
Esquire Visual Director: James Morris @j_alexander_photo
Esquire Entertainment Director: Andrea Cuttler @angcutt
Esquire Editor-in-chief: Michael Sebastian @michaeljsebastian