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Brad Pitt wears a Celine by Hedi Slimane tank top, pants, and sunglasses; Tom Ford boots; his own jewelry and watch.

Photograph by Juergen Teller; Creative Partner to Juergen Teller: Dovile Drizyte; Styled by Sara Moonves. Skin by Stacey Panepinto; Hair by Malcolm Edwards at LGA Management; Manicure by Michelle Saunders.

He's been one of the biggest stars in the world for almost three decades, but Brad Pitt had to claw his way into Hollywood like anyone else. On this video episode of "Five Firsts", the Once Upon a Time... In Hollywood star sits down with Lynn Hirschberg to reflect on his early days as an extra, when he was still struggling to get a Screen Actor's Guild card.

Hoping to sneak in a speaking part during a scene in which he was asked to silently pour champagne, he decided to improvise—and it almost got him kicked off the set. "They grabbed me to be, like, the waiter. It was a big dinner scene at a restaurant, and they had me pour champagne in the glasses, and I thought, I'm gonna try to get a line in," he recalls.

"I poured one, maybe it was Charlie's, I don't know, and then another actor's, and then I got to this actress at the end and I poured her drink, and then I looked at her and I said, 'Would you like anything else?' She looked at me and went, 'Ugh.' Yeah, the first AD goes, 'Cut, cut, cut, cut,' and he came over to me and he said, 'You do that again, you're off the set.'"

Pitt also tells Hirschberg about his first kiss, attending two different proms in high school, and how he related to his character in Once Upon a Time... In Hollywood from the first time he read the script at director Quentin Tarantino's home.

"It was a guy who was pretty at peace with his place in life, knew what he was dedicated to, what he was not dedicated to, looked for the best in people but was not surprised to get the worst in people. I could relate to that. And he gets to drive through LA in a really cool car," Pitt says. "Well, you know that comes with a Tarantino movie. You're gonna get a cool car. You're not gonna get some shit box."

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