In the premiere episode, the Once Upon a Time In Hollywood star worked with the Scott brothers to renovate the guesthouse of his longtime friend and makeup artist, Jean Ann Black — who Pitt says is “like family” to him — while she’s out of town.
“She’s family. We’re like brother and sister,” Pitt tells the Scott brothers as they prepare to renovate a back garage at Black’s Santa Monica home into a guest house that can double as a workspace and storage area for her makeup supplies. “Even if I tank a scene, she’s always right there telling me, ‘Hey, it’s all right.'”
“Makeup is a lot about trust,” Black adds of her longstanding relationships with stars like Pitt, Julia Roberts, Josh Brolin and more. “It’s not always about how great you are at makeup. It’s how much you can understand people.”
That trust can sometimes extend to some uncomfortable scenes, as Pitt jokingly recounts, “There was a time, on Legends of the Fall, she had to makeup my butt because of bad tan lines. When it comes up, we can’t really look each other in the eye.”
“This will mean so much to her,” Pitt says, growing teary-eyed as the brothers reveal some extra touches they’ve added to the space, like a makeup mirror and a special tribute to Black’s late parents. “I’m the guy who’s gonna cry on television. I can’t take it in just yet, what it will mean to her, and all the people she helps, and how much she means to me. It’s just great.”
The Scott brothers themselves were “blown away” by how “down to earth” and pleasant Pitt was while filming.
“He wanted everybody to feel like he was spending some time getting to know them,” said Jonathan Scott. “And at the very end he remembered every single person’s name on the production crew and on the construction crew. He remembered everybody and wanted to make sure that they knew how grateful he was for what was happening. He was a true gentleman in every sense of the word.”