I just heard from Timothy Olyphant himself about his part in the new movie, The Adventures of Cliff Booth, and it sounds like he’s playing a surprisingly significant role as James Stacy. It’s bigger than I initially thought, and I’m definitely intrigued to see what he brings to the character.
The actor originally portrayed James in Quentin Tarantino’s Once Upon a Time in Hollywood. Now, in The Adventures of Cliff Booth, both Olyphant and Brad Pitt are back – with Pitt reprising his role as Cliff Booth, who evolves from stuntman to studio problem-solver in the world of Hollywood.
Timothy Olyphant shared on the SmartLess podcast with Jason Bateman, Sean Hayes, and Will Arnett that he makes a “very brief” appearance in The Adventures of Cliff Booth. He said filming his scenes only took a day and a half.
Rather than Quentin Tarantino, the highly respected director David Fincher – known for films like Alien 3, Fight Club, and The Curious Case of Benjamin Button – directed the movie.
Timothy Olyphant described working with David Fincher as a highly technical process. It’s common for directors to ask for multiple takes, but Fincher took this to another level while filming The Adventures of Cliff Booth.
The actor explained that the director would often give very precise instructions, like asking him to adjust his hand slightly for each take. He recalled being told to “move it just an inch left, okay, now down just half an inch. Lift it right there.”
He explained that creating the visuals for the project became incredibly complex, so much so that filming a single scene took him a day and a half.
I spent about two and a half days filming one scene – something I’d never experienced before. It felt like an initiation, constantly being asked to do another take with a lot of energy and enthusiasm. I really wanted to be involved and contribute to the project; it was incredibly motivating.
We’re working through the details, making small adjustments – a little to the left, a bit down. It’s very precise, visually and in terms of timing. It’s like rehearsing a scene repeatedly – maybe twenty times in a row, then another twenty. We spend a day and a half focusing on just this one part, refining it over and over.
Even though the work was very detailed and demanding, Olyphant still enjoyed being on set and acting. He’d reached a point where he felt it was worth perfecting every scene, even if it took many tries – as he put it, “life’s too short” to settle for less, particularly when working with a director as skilled as Fincher.
I only had a small role, but I really enjoyed being involved. We filmed for a day and a half, and I worked on set for the second day. It was a fascinating experience, and I loved it. I used to think the project was something I’d avoid – life’s too short, I thought – but I was in a different headspace this time. I was happy to put in the effort and do multiple takes.
During filming, Olyphant struggled with self-doubt. He explained that repeating the same actions so many times made it difficult to ignore the feeling that he was messing up, and he said that giving in to that feeling was the biggest problem.
The actor explained that while a successful take initially boosts his confidence, repeatedly having to redo the scene – sometimes fifteen or more times – can lead to self-doubt. He emphasized the importance of ignoring that negative inner critic and staying focused.
It’s strange how, after repeating something many times, you begin to doubt yourself and worry about making mistakes – that self-doubt can ruin everything. It also starts to mess with your natural instincts. It’s like being put through a test where they try to wear you down, but you refuse to give in. When you nail a take and feel great about it, the knowledge that you have fifteen more to go can suddenly make you question if it was actually good. You really need to ignore that negative voice in your head.
I admit this might sound strange, but for about ten years now, my process has been to learn my lines completely, then rehearse them until I’m almost numb. The idea is to arrive on set feeling fully prepared. But once you’re there, things change and require adjustment. It’s hard to deliver a convincing performance when everyone’s aware of the less-than-ideal conditions – like a messy or inadequate craft services table.
Released in 2019, Once Upon a Time in Hollywood was well-received by critics, earning an 86% rating on Rotten Tomatoes. The film proved successful commercially, bringing in $393.9 million worldwide. It also received significant awards recognition with 10 Academy Award nominations, winning Oscars for Best Supporting Actor (Brad Pitt) and Best Production Design.
As a total film buff, I was completely drawn into this movie set in 1969 Los Angeles. It follows Rick Dalton, played by Leonardo DiCaprio, and his longtime stunt double, Cliff Booth, as they navigate the changing world of the movie industry. What makes it even more fascinating is that all this is happening during the height of Charles Manson’s terrifying influence and the rise of his cult.
Tim Olyphant and Brad Pitt will reprise their roles in the follow-up to Once Upon a Time in Hollywood. Joining them will be Elizabeth Debicki, Scott Caan, Carla Gugino, Yahya Abdul-Mateen II, Peter Weller, JB Tadena, Corey Fogelmanis, Karren Karagulian, Holt McCallany, Barry Livingston, and Lauren Glazier.
You’ll be able to see The Adventures of Cliff Booth in IMAX theaters for two weeks starting November 25th, and then it will be available to stream on Netflix beginning December 23, 2026.
2026-07-20 21:10