The Daily Show: October 23, 2025 - Jeff Tweedy

Overview

Michael Kosta dives into the alleged involvement of Portland Trail Blazers head coach Chauncey Billups and Miami Heat star Terry Rozier in illegal gambling schemes. Plus, Donald Trump continues to defend the construction of his mega-sized White House ballroom as he fully demolishes the East Wing. And Josh Johnson thanks the contractor-in-chief on behalf of waltz-loving podcast bros everywhere. Jeff Tweedy, Grammy award-winning frontman of the band Wilco and bestselling author, sits down with Michael Kosta to discuss his new solo album, "Twilight Override," named to evoke his feeling of getting older and watching a world that "appears to be getting darker." Tweedy also discusses why he's glad to have spent his formative years as a musician in the midwest, his theory that repressed trauma after Covid is one cause of present-day chaos, and the need for everyone to spend less time on their phones and more time with people who love them.