"Timothy Olyphant"

The episode begins with sponsored segments for Hotels.com, Apple Card, and Amazon Health AI before diving into Timothy Olyphant's interview. The hosts discuss childhood experiences with cheating and theft, with one host recounting a story about being arrested for stealing a turkey sandwich while drunk in college. Timothy shares his background, revealing he grew up in Modesto and attended USC as a fine art major, eventually receiving his degree in fine arts after 32 years following his current career success. He studied under professor Ruth Weisberg and chose to complete his degree while his children were finishing high school.

The conversation explores Timothy's path to acting, noting he never initially planned it but wanted to try multiple creative pursuits including stand-up comedy, acting, and being in a band before committing to fine art. The hosts discuss the range required in acting, with Timothy expressing admiration for Robert De Niro's ability to blend comedic and dramatic performance. They explore the concept of "sing for real"—a game where someone must sing a song from the radio authentically without performance tricks.

Timothy discusses his television work extensively. He spent three years on Deadwood and six years on Justified, working alongside actors like Margot Martindale. He shares a memorable anecdote about creator David Milch knocking on his trailer to announce the decision to kill off his character's son in the storyline, framed positively as creating better material for Timothy. He mentions his lack of a computer or laptop and his phone-less lifestyle, noting the advantages of unpredictability when making plans without constant contact.

The discussion turns to recent and upcoming projects: season two of Alien: Earth will shoot in London instead of Thailand; Stick season two is renewed; Lucky is an Apple TV crime thriller with Anya Taylor-Joy and Annette Bening; The Five-Star Weekend features Jennifer Garner on Peacock; and Adventures of Cliff Booth is a Quentin Tarantino sequel directed by David Fincher. Timothy describes his extensive experience working with Fincher, who conducted a day-and-a-half shoot for a brief scene, doing 20+ takes of master coverage and push-ins with technical precision about hand placement, timing, and performance nuance.

The hosts discuss directorial approaches and note styles. Soderbergh gave minimal notes (one exchange rating a performance "seven or eight out of ten"), while Bradley Cooper similarly operates cameras and gives minimal feedback. The episode concludes with promotion of the SmartLess live show at the Hollywood Bowl on October 17th, accessible through smartlist.com/live.