Oscar-winning actor & musician Keith Carradine joins Jay to discuss growing up in a legendary Hollywood family and carving out his own path as a character actor. Keith reflects on career-defining roles, working with icons, and the philosophy that’s guided his decades in the business. The episode bounces between old-school showbiz stories, Deadwood memories, the unlikely journey of his Oscar-winning song “I’m Easy”, a house bunny named Clooney, and much more.
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