Season 1

1. Lending People Money

John sits with guests Michael Keaton, Joan Baez, Fred Armisen and personal finance columnist Jessica Roy. Musical guest Cypress Hill performs.

2025-03-12 • 58 min

2. Cruises

John sits with guests Ben Stiller, Nick Kroll, Quinta Brunson and cruise industry expert Anne Kalosh. Musical guests Kim Gordon and Kim Deal perform.

2025-03-19 • 60 min

3. Funeral Planning

John sits with guests Pete Davidson, Henry Winkler, Luenell and funeral director Raymundo Perez-Plasencia. Musical guest Mannequin Pussy performs.

2025-03-26 • 58 min

4. Squatters

John sits with Wanda Sykes, John Waters, Stavros Halkias and Supreme Court lawyer Neal Katyal. Music by Daniel Hope and New Century Chamber Orchestra.

2025-04-02 • 59 min

5. Getting Fired

John sits with Bill Hader, Johnny Knoxville, Chelsea Peretti and HR executive and employee coach Catie Maillard. Musical guest Bartees Strange.

2025-04-09 • 60 min

6. Heights

John is live with guests David Letterman, Hannibal Buress, Leanne Morgan and Nikki Glaser. Musical performance by Randy Newman.

2025-04-16 • 60 min

7. Are Dinosaurs Put Together Correctly?

John discusses whether dinosaurs are put together correctly with Conan O’Brien, Ayo Edebiri and Tina Fey. Music by Metz.

2025-04-23 • 61 min

8. Can Major Surgery Be Fun?

John discusses if you should get surgery with guests Molly Shannon, Marc Maron and Ronny Chieng. Music by John Cale and Maggie Rogers.

2025-04-30 • 60 min

9. Are You Ready for Real ID?

John asks if you're ready for Real ID with Robby Hoffman, Ramy Youssef, Andy Samberg and expert Aixa Diaz. Music by Destroyer and Jessica Pratt.

2025-05-07 • 60 min

10. Why Can't I Sleep?

John discusses sleep issues with Sarah Silverman, Patton Oswalt, Steve Guttenberg and neuroscientist Dr. Rahul Jandial. Music by Alanis Morissette.

2025-05-14 • 62 min

11. Is Uber Good?

John asks if Uber is good with guests Sigourney Weaver, Natasha Lyonne, Amy Sedaris and transit expert Alissa Walker. Music by Yeule.

2025-05-21 • 61 min

12. What Is on the Minds of Teens?

John fights three 14-year-olds and asks what's on the minds of teens with Sean Penn, Joe Mande and more. Music by Sleater-Kinney with Fred Armisen.

2025-05-28 • 69 min