What began as a romantic affair with his co-star on the set of Mr. & Mrs. Smith, became a new chapter in the actor's life - the origins of the former couple Brangelina.
Brad also inherited Angelina's adopted children Maddox and Zahara, then went on to share Shiloh, Pax, and twins Knox and Vivienne with the actress.
In an interview with GQ, theOnce Upon A Time In Hollywoodactor admitted that during the "late '90s or early 2000s" - the years that he was with Jennifer - he was "failing to live as interesting a life" as he thought he could.
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Brad discussed his motivation for taking on the role of stuntman Cliff Booth in the Quentin Tarantino film, opposite Leonardo DiCaprio as Rick Dalton.
"Well, it’s about bringing my personal experience, my personal humour, my personal, um, embarrassments, and my personal pains," he explained. "When I watch [Christian] Bale or [Tom] Hardy, I can’t do what they do. I love watching them. And I couldn’t step into that role. I want to do the same thing on my end."
The 55-year-old revealed that he had told co-star Leonardo that he didn't feel that he was living an interesting life during the '90s and '2000s.
Brad Pitt and Jennifer Aniston were together throughout the '90s and '2000s before he fell in love with co-star Angelina Jolie on the set of Mr. & Mrs. Smith.
Brad also told the publication that he still enjoyed acting, but he didn't want to centre his life around it anymore or live through his roles.
"There was just too much emphasis on finding interesting characters. I went, ‘F*** me, man. Live an interesting life and the rest will take care of itself.’ Like, ‘You go out and you…live an interesting life. Get out and have real experiences.’ Andthatis what informs the work. Not going to find the interesting work and then trying to make it up. I just became more conscious of how I was living versus what I was living for."