Timothy Olyphant’s Return In Netflix’s Adventures Of Cliff Booth Gets Disappointing New Update

Published Jul 20, 2026, 2:04 PM EDT

The actor first played James in the Quentin Tarantino-directed Once Upon a Time in Hollywood. The Adventures of Cliff Booth is a sequel that sees both Olyphant and Brad Pitt returning to the franchise, with the latter once again playing the titular character, Cliff Booth, as the stuntman rises up to become a studio fixer in Hollywood.

During an interview on Jason Bateman, Sean Hayes and Will Arnett's podcast SmartLess, Olyphant revealed that he appears "very briefly" in The Adventures of Cliff Booth. His scenes only took a day and a half to film on set.

Instead of Tarantino, though, acclaimed filmmaker David Fincher, who helmed such movies as Alien 3, Fight Club and The Curious Case of Benjamin Button, sat in the director's chair.

Olyphant found working for Fincher to be a very technical filming experience. While it's normal on a set for scenes to be shot multiple times, the way this unfolded on the set of The Adventures of Cliff Booth was extreme.

As an example, the actor said that if he had to lift his hand up, the next take would see him having to "move it just an inch left. Okay, now down just half an inch. Lift it right there."

He added that the production could get "super, super technical visually," which led to him taking a day and a half to film just one scene.

"I did a scene for like two days, day and a half. I'd never done that anything like it. I felt like I was pledging a fraternity. Felt a little bit like, oh, let's go again. Let's do it. F*** yeah. I want to be part of this. Let's go.

"It's, okay, on that moment, you know, maybe this. And then when you lift your hand up, show me where it is. Okay, now move it just an inch left. Okay, now down just a half an inch. Lift it right there. And you're like, okay, it's a lot of that. So it's everything from when you lean forward, don't lean quite that far. A little there. It can get super, super technical visually, but it can also get very, very specific about when you do that, maybe it's more of an order. It's almost like doing a run of a play, like a scene, but you're doing it so many times, you're doing it the master, you're doing like 20 times and then you're pushing 20 times. So for a day and a half, you're just doing this scene.

Despite how technical the experience was, Olyphant still loved being on set and going through the motions. At this point in his life, he realized that it's fine to do 30 takes on one scene because "life's too short" not to get it right, especially when working under the direction of someone like Fincher.

"I'm very briefly in it. So I'm showing up for this thing and I don't know how many pages that was, but we shot it for a day and a half. My coverage was day two. It was fascinating, so I loved it. I really loved it. And I think years ago when I was reading about him, I just thought, 'No f****ing way. Life's too short.' But for whatever reason at this point in my life, I just was like, 'Yeah, let's do 30 takes. Great.'"

However, there did come a point during filming when Olyphant had to battle with his own mind. "You're doing it so many times, it's hard to shut out the voice that feels like you're doing it wrong. And that's the kiss of death," he admitted.

The actor added that after shooting a great take, his confidence swelled, but then having to do it over again 15 more times, "you start to go, maybe it wasn't that good...You have to shut that voice out."

"There's a surreal quality that starts to happen that you don't expect, which is you're doing it so many times, it's hard to shut out the voice that feels like you're doing it wrong. And that's the kiss of death, right? You also start to lose your instincts because—it's like pledging the fraternity here and they're going to break me down, and I'm not going to crack. If you do a great take...you finish a take and you think that just felt so money. The fact that you're going to do 15 more after that take, you start to go, maybe it wasn't that good. You have to shut that voice out.

"I say this with a grain of salt, but for the most part my technique for the last decade or so has been memorizing the lines and then memorizing them to exhaustion so I show up hopefully in that place. So then to show up and then keep going, you have to readjust. How would you expect me to act that well when you've seen the craft service table, and we both know that's f***ed up?"

Once Upon a Time in Hollywood came out in 2019 and received positive reviews from critics, who gave it an 86% score on Rotten Tomatoes. At the box office, the film grossed $393.9 million and earned 10 Oscar nominations, winning for Best Supporting Actor (Pitt) and Best Production Design.

The story, which takes place in 1969 Los Angeles, revolves around Leonardo DiCaprio's Rick Dalton and stunt double Cliff Booth in the movie industry at the same time that Charles Manson is at the height of his power as a cult leader.

Only Olyphant and Pitt are returning for the Once Upon a Time in Hollywood sequel. They'll be joined by 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.

The Adventures of Cliff Booth will be released in IMAX theaters for two weeks beginning November 25 and then released on Netflix on December 23, 2026.