Timothy Olyphant may have accidentally revealed his potential role in Quentin Tarantino's Once Upon a Time in Hollywood 

On the August 8, 2025 episode of Conan O’Brien Needs a Friend, Timothy Olyphant seemed to have dropped a hint of being a part of The Adventures of Cliff Booth, the sequel to Quentin Tarantino's Once Upon a Time in Hollywood.

When Conan mentioned the sequel, the show's co-host Matt Gourley confirmed that it was written by Quentin Tarantino and directed by David Fincher. Olyphant casually replied, "Yep," and said, "I'm in it." He soon realised the slip-up and stated that he wasn't sure about his involvement.

Distributed by Netflix, Quentin Tarantino's sequel is in early development. It features several new faces in the ensemble cast alongside Brad Pitt, who is reprising his role from the original film.

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Timothy Olyphant fuels speculation on his possible role in Quentin Tarantino's comedy-drama sequel

During the podcast episode, Olyphant might have slipped up about his possible involvement in Quentin Tarantino's sequel when the show's hosts mentioned the upcoming film. He didn't explicitly confirm it, but the on-air blunder has prompted rumors that he might be in the eagerly awaited Tarantino's follow-up.

The Grinder fame stated that he only found out about the opportunity a few weeks ago and that he’s still uncertain about whether he’ll be taking on the role in Quentin Tarantino's sequel. Conan teased him about keeping the scoop from him, prompting Olyphant’s sarcastic reply that the latter hadn’t even seen him in weeks.

In the original, Olyphant portrayed James Stacy, a real-life actor best known for his appearance in the Western TV series Lancer. Acting opposite Leonardo DiCaprio's character, Rick Dalton, in a TV shoot set inside the movie, Olyphant's Stacy makes an appearance during a fictionalized Lancer set piece.

With a screenply by Quetin Taratino, The Adventures of Cliff Booth, reunites David Fincher and Brad Pitt in a remarkable return to the iconic role of stuntman Cliff Booth. The film features new ensemble including Scott Caan, Elizabeth Debicki, Yahya Abdul-Mateen II, Carla Gugino, JB Tadena and Corey Fogelmanis among others.

The filming began on July 28, 2025 in California, using period-appropriate settings like Highland Park’s historic Highland Theatre. The production is expected to continue into early 2026, and the filmed will be released on Netflix.

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What was the plot of Once Upon a Time in Hollywood?

Once Upon a Time in Hollywood (Image via Prime Video)

Quentin Tarantino's Once Upon a Time in Hollywood centers on Rick Dalton (Leonardo DiCaprio), a fading television celebrity who was famous for his roles in a popular western series, and his stunt double and best friend Cliff Booth (Brad Pitt).

Cliff serves as Rick's confidant and driver while dealing with allegations about his past as Rick tries to adjust to a transitioning film industry. Their lives intersect with real historical figures, most notably Sharon Tate (Margot Robbie), a rising actress married to director Roman Polanski.

The film revisits the infamous Manson Family cult, who actually carried out the Tate–LaBianca murders, while simultaneously following the fictional adventure of Rick and Cliff. Events drastically change in Tarantino's version.

It reinvents history with dark comedy and violent outbursts while paying tribute to the 1960s Hollywood's fashion, music, and television culture. The film explores friendship, fading celebrity, and the timeless power of film through a blend of heartwarming character moments and twists and turns.

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