By Dustin Rowles | News | August 4, 2025
Timothy Olyphant — professional late-night talk-show guest turned professional podcast guest — appeared once again on Conan O’Brien’s podcast this week, where he does his best work (he’s also an actor of some acclaim, but that’s less important).
The hook? Olyphant accidentally revealed that he’s been cast in David Fincher’s sequel to Quentin Tarantino’s Once Upon a Time… in Hollywood, where he’ll presumably reprise his role as James Stacy for the Netflix project. He didn’t mean to spill the news — Matt Gourley casually brought up the sequel, and Olyphant, in a moment of self-satisfied mime, indicated he was in it … before realizing the podcast was being recorded on video. (It’s OK. Gourley gave him an out, but Olyphant refused, and Conan complained that he hadn’t shared the scoop with him directly.) The moment happens around the 43-minute mark in the video below.
Of course, no one watches just a minute of a Conan/Olyphant podcast. In the lead-up to the Once Upon a Time moment, Olyphant also shared that he worked on a “really bad movie” with Damian Lewis (which he still found really fun to make), and — perhaps to Olyphant’s consternation — Gourley correctly guessed it was Dreamcatcher.
After the Once Upon a Time reveal, Olyphant tells an even better story about working in Thailand and using Google Translate to ask waiters, “What is your favorite?” or so he thought. When he later spoke the same Thai phrase into Google Translate, he learned he’d actually been asking every waiter to “Gaze into my eyes.”
Olyphant never let us down. (And with apologies to Andrew for stealing the Conan story before him).
via The AVClub