Brad Pitt starred as free spirited, stuntman Cliff Booth – a laidback loner who had more success picking up cute hippy chicks in late 60s Los Angeles than finding employment in Quentin Tarantino’s masterpiece, Once Upon a Time… in Hollywood.
The 60s were almost at an end, the hippy, free love movement fading, and evil was brewing under the surface in LA. Set in the summer of 1969, Once Upon a Time… in Hollywood tells the story of the people on the fringe of society in the city of angels – out-of-work actor Rick Dalton (Leonardo DiCaprio), who is Cliff’s drinking buddy and neighbor to film producer Roman Polanski and his pregnant wife, Valley of the Dolls actress, Sharon Tate (played by Margot Robbie). And, a couple of hundred miles away in the less exclusive part of town, the Manson Family – a sinister cult who were behind a series of assaults, murders and attempted murders.
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Brad Pitt to revive laid-back stuntman Cliff Booth
Brad Pitt’s memorable performance in Once Upon a Time… in Hollywood earned him the Oscar for Best Supporting Actor at the 92nd Academy Awards.
The 61-year-old has resurrected Cliff Booth for a Netflix-backed spin-off directed by David Fincher which is due to start filming next month. “This is something Quentin Tarantino wrote,” Pitt revealed during the London premiere of his new Formula 1 film. “It’s more of a standalone episode than a direct sequel. Quentin didn’t want to direct it himself at this stage, so our friend David Fincher stepped in.”
#F1TheMovie star Brad Pitt discusses ‘The Adventures Of Cliff Booth’ and reveals that he’s going to start filming it in July: “This is something Quentin Tarantino wrote. It’s an episode, not really a sequel, of the character from ‘Once Upon A Time’. He didn’t want to direct it at… pic.twitter.com/7YXJFisqUH
— Deadline (@DEADLINE) June 23, 2025
Brad Pitt on all the great things about working with Tarantino
And he looked back on Once Upon a Time… in Hollywood in a recent chat with Dax Shepard, who confessed that he is obsessed with the movie, watching it eight times in 18 months.
There was one question that Dax was keen to ask Brad – if starring in a Tarantino film ruins the experience of going to watch it when it comes out.
“There is no bummer about being in a Tarantino movie,” Pitt immediately replied. “That dialogue is just like… c’mon!” And when asked about balancing the scenes so that Cliff didn’t steal the limelight from the film’s lead, DiCaprio’s washed-up Rick Dalton , he said: “That’s the thing that’s least understood is the degree of difficulty. And even we’ll get credit for [the work done by] a great director or great writing, great editing… He was doing multiple layers in there, and that star tantrum cracks me up”.
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