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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