14 best Armchair Expert episodes, from Brad Pitt and Cher to Kristen Bell

Published on 10/07/2026 Federico Vargas

Brad Pitt on getting sober, Cher telling Dax his wife deserves better, Conan O’Brien on crashing a bicycle. These are the Armchair Expert episodes worth your next two hours.

Dax Shepard has recorded more than a thousand conversations in the attic, and a lot of them are good. These 14 are the ones I keep sending to friends. Press play on any of them and you will see why Armchair Expert with Dax Shepard keeps such a loyal crowd.

Cher

Release date: January 5, 2026
Duration: 1 hour, 59 minutes

Cher

01/05/2026 01:58:51

Cher tells Dax his wife deserves better, to his face. That line made the headlines in January, and she means it as a compliment to Kristen Bell. The rest of the episode is just as direct. Cher walks through why her earlier attempts at a memoir failed, singing backup in Phil Spector’s studio before anyone knew her name, stumbling into her first acting job with Robert Altman, and the Burlesque set where she met Kristen. She calls herself a woman who has always worked, not an icon. After two hours, you believe her.

Brad Pitt

Release date: June 23, 2025
Duration: 2 hours, 8 minutes

Brad Pitt

06/23/2025 02:08:13

A movie star with the press-junket armor off. Brad Pitt and Dax got to know each other at a twelve-step meeting, and it shows: this is two sober friends talking. Pitt covers leaving college one week short of his degree to try Hollywood, getting shut down when he tried to get his SAG card, and the high of delivering lines at 180 miles per hour on F1 The Movie. His joke that if he ever had a gay experience, it would not be with Dax went everywhere within a day. The full two hours are better than the clip.

Paul Giamatti

Release date: January 8, 2024
Duration: 2 hours

Laurie Santos

05/21/2020 01:28:21

He will teach you a thing or two. Here’s to starting the year with a bang. Paul Giamatti chats about his acting path, spilling details about growing up in a family of actors and his passion for the stage. He gets real about his own challenges and guilty pleasures. Listening to him, you really get pulled into the world of a dynamic performer. How does it feel to be the bad guy in the movie? His tales and thoughts genuinely grabbed my attention.

David Letterman

Release date: March 22, 2023
Duration: 1 hour 40 minutes

A legend’s perspective. David Letterman dives into his life after hanging up his late-night suit, sharing how he approaches interviews and the lessons he’s learned since his heart surgery. Chatting with Dax, he sprinkles in wisdom, humor, and even some unexpected bear chatter. If you love deep talks with a quirky edge, you will find this episode fantastic.

Nov ’21 Spotify Exclusive: Bradley Cooper

Release date: November 29, 2021
Duration: 1 hour 53 minutes

A peek behind the curtain. Bradley Cooper joins his old friend Dax Shepard in this laid-back chat. They dive into everything from their journey to sobriety to Cooper’s infectious laughter. It’s like sitting in on a conversation between two pals, full of light-hearted yet meaningful stories. This one had me smiling from start to finish.

Episode 171 – Ronan Farrow

Release Date: January 13, 2020
Duration: 1 hour, 50 minutes

Intrigue and Inspiration. Ronan Farrow brings intrigue and inspiration to the attic. His stories, from being a child prodigy to a journalist exposing Hollywood’s dark secrets, are nothing short of compelling. I found myself hanging on every word. This episode isn’t just informative; it’s a fascinating look into a life that’s anything but ordinary.

Episode 158 – Emilia Clarke

Release date: November 18, 2019
Duration: 2 hours, 16 minutes

Hey, Game of Thrones fans! Ever wondered what Daenerys Targaryen is like in real life? Emilia Clarke spills the beans in this Armchair Expert episode. She’s surprisingly down-to-earth, sharing juicy Game of Thrones details and opening up about her challenging experiences with brain hemorrhages. It’s a mix of fun facts and deep, personal stories. You won’t want to miss this one.

Episode 149 – Monica Lewinsky

Release Date: October 14, 2019
Duration: 1 hour, 38 minutes

Resilience and New Beginnings. Monica Lewinsky steps into the attic, and the atmosphere shifts to something deeply meaningful. She talks about her past with a rare, raw honesty. But it’s her transformation into an advocate against bullying that really impressed me. Listening to her story, you can’t help but feel empowered and moved. It’s an episode that reminds us of the power of resilience and new beginnings.

Episode 147: Dr. Nadine Burke Harris

Release date: October 10, 2019
Duration: 2 hours, 8 minutes

Eye-opening and empathetic. Dr. Nadine Burke Harris discusses Adverse Childhood Experiences (ACEs) with Dax, explaining how childhood trauma impacts life. This talk is a real eye-opener. It helps you get where others are coming from and really amps up your empathy. If you want to learn about public health and personal stories, this is your go-to episode.

Episode 35 – Jason Bateman

Release Date: June 25, 2018
Duration: 1 hour, 23 minutes

A Lesson in Friendship. Ever wanted to be a fly on the wall during a celebrity heart-to-heart? Episode 35 is your ticket. Dax Shepard and Jason Bateman chat about everything from sobriety to their early scumbag days. It’s honest, it’s relatable, and it’s filled with moments that’ll have you nodding along. Not just a conversation but a lesson in friendship and the journeys we all navigate.

Episode 25 – Dax’s Mom (Laura Labo)

Release Date: May 7, 2018
Duration: 1 hour, 15 minutes

Episode 59 – Conan O’Brien

Release date: November 26, 2018
Duration: 1 hour, 56 minutes

Get ready to laugh! Conan O’Brien brings his unique humor to this episode. From hilarious stories about bicycle accidents to his views on life, O’Brien doesn’t hold back. It’s a playful, engaging conversation that proves why late-night hosts are great interviewees.

Esther Perel

Release date: May 2, 2019
Duration: 2 hours, 16 minutes

A deep dive into relationships. In this episode, Dax teams up with Esther Perel, the famous therapist, to dive into some pretty fascinating stuff like eroticism, what we expect from relationships, and how a couple’s vibe affects their family. They really get into challenging what we think is normal and how we see ourselves. If you’re curious about the nitty-gritty of relationships, you’ve got to give this one a listen.

Episode 1 – Kristen Bell

Release date: February 14, 2018
Duration: 2 hours

A raw, honest look at a Hollywood couple. Dax Shepard starts his podcast journey with his wife, Kristen Bell. They’re open about their relationship’s ups and downs, giving us a real peek into their lives and making a fresh start for this podcast. It’s a bit tense but sincere and relatable. You’ll see why they’re a couple we all love and relate to, flaws and all.

Jumping into Armchair Expert feels like opening a box full of fascinating stories. Every episode has its unique charm, offering new perspectives on the world. Looking for laughs, inspiration, or just great entertainment? These episodes got you covered. Why not tune in? Your new favorite story could be just a play away. Here’s to continuing our adventure, episode by episode.

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