All of Brad Pitt’s Hollywood Moments From W’s Archive

Brad Pitt may have played an astronaut flung into space in his film Ad Astra, or the mythic character Tyler Durden in Fight Club—but longtime readers of W know that Pitt has always seemed otherworldly. For his four solo covers of the magazine (and one infamous joint cover with his now-ex, Angelina Jolie), Pitt has been photographed by Steven Klein, Chuck Close, Mario Sorrenti, and Juergen Teller. As much as he’s evolved for the screen (a place from which, at 55 years old, he has decided to slowly remove himself), Pitt has also evolved for W. Ever since he first landed a cover in 1999, the photos of Pitt that can be dug up from the W archives depict him in many roles, most of which engage with different takes on masculinity and all of which could be described as sex symbols: the domestic family man playing house in Palm Springs, the classic silver screen actor, reminiscent of the golden days of Tinseltown—and most recently, himself, on the streets of Los Angeles, in our Best Performances issue. Revisit the rest of Pitt’s greatest hits from the W archives, here.