Armchair Expert with Dax Shepard Armchair Expert with Dax Shepard

Armchair Anonymous: Jail

Nov 6, 2026 · 37m

Summary

In this episode of Armchair Expert, Dax Shepard and Monica Lewinsky interview three guests about their unexpected jail experiences. Jordan recounts a wild night in Austin where he fell through a bank skylight and was arrested, while Chris describes getting booked into a New York jail after throwing a bottle from a rooftop bar. Erica shares her story of being arrested for reckless endangerment after a Roman candle hit a police car during a Fourth of July celebration.

Topics discussed

Introduction and topic: jail stories Sponsor: Quince holiday gifting Sponsor: McDonald's Quarter Pounder deal Guest intro: Ben Affleck and Bell's palsy Austin rooftop adventure begins Exploring rooftops and finding a game room Attacking the skylight and fleeing Police chase and the 'punks' lie Arrest and booking process Jail time and the bank atrium reveal Google Earth verification and Harley dream Sponsors: Gusto and NoBull Sponsors: NoBull shoes and Helix mattress Sponsor: BetterHelp therapy Guest intro: Chris from Southwest Chris's story: Mr. Purple rooftop bar Bottle throwing and police intervention Arrest and the missing inhaler Locked out of the cop car Jail cell conditions and cellmates Sponsors: Squarespace and Walden University Sponsor: Superhuman Go Jail antics and the 'Ken Doll' nickname Phone calls and sentencing Rekindled relationship and shirt gag Guest intro: Erica from Denver Erica's story: 4th of July fireworks Firework incident and police encounter Arrest, classes, and record expungement Closing remarks and family stories Random questions and theme song Sponsor: Allstate insurance
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