This is an episode about history. Collective history and personal history. Marc finds himself in Washington, DC on the latest leg of his standup tour, a place imbued with symbolism, both for what we want it to be, but also what we really are. And it's where Marc's college roommate lives. First, Marc reckons with a history of injustice at the Smithsonian National Museum of African American History and Culture with curator Dr. Dwandalyn Reece. Then Marc tries to piece together his own past with his old roommate, Lance Mion.

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Michael Che wanted out his life on the Lower East Side, but his initial path was not comedy. It was painting and fine art. Michael tells Marc how he became enamored with standup while living in his brother's basement, how he came to love the grind of building an act, and how he puts everything he's learned into his sketch show, That Damn Michael Che. They also talk about the growing pains of doing Weekend Update on SNL and why hosting award shows isn't all it's cracked up to be.

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Sandra Oh spent much of her career believing certain opportunities weren't going to come her way because they're just not afforded to Asian actors. Sandra and Marc talk about what she found in herself to overcome that sense of externally imposed limitations and how she built a body of work including Grey's Anatomy, Sideways, Killing Eve and The Chair. Sandra also explains how she's drawing inspiration from John C. Reilly in this next phase of her life as an actor.

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The Doobie Brothers is a band with almost twenty official members throughout its five decades of existence. But Tom Johnston and Pat Simmons have been playing guitar and performing vocals for the band since Day One. Tom and Pat talk with Marc about how their family-like band has grown and evolved throughout the years, particularly during iterations with members like Jeff “Skunk” Baxter and Michael McDonald. Also, during his time in Tulsa, Marc pays a visit to the new Bob Dylan Center and talks with its director, Steven Jenkins.

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Marc remembers the life and comedy of Dan Vitale, a comedian whose raw and unapologetically personal style of stand-up was a big influence on a young Marc Maron. Marc talks about how his perception of what it meant to be a stand-up comic changed while watching Dan, how their talk in 2014 exemplified WTF, and how the connection they maintained in the following years helped Marc through the darkness. Marc also shares the entirety of Dan's episode from March 2014.

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Nicole Holofcener has trouble breathing. She finds herself holding her breath for too long, which could be a result of allergies or a byproduct of sleep apnea. But it's also an apt metaphor for the life of an independent filmmaker. Nicole and Marc talk about what it takes to make films with small budgets, casting conundrums, and deeply personal subject matter. They discuss the films she wrote and directed like Walking and Talking, Lovely and Amazing, and Enough Said, as well as her contributions to The Last Duel and her reasons for continuing to work on episodic television shows.

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Tony Hawk walked into Marc's garage on a broken leg, the result of a recent skateboarding trick gone wrong. It's everything about Tony that's on display in the new documentary Tony Hawk: Until The Wheels Fall Off, distilled down to one cracked femur. Tony and Marc talk about why it's so hard to stop doing what you love, the fear of being seen as washed up, and the feeling of being a kid and finding something that you know you want to do for the rest of your life.

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It's normal for everyone to call Troy Andrews by his stage name, Trombone Shorty, because he's been playing the trombone since he was a tiny, four-year-old boy. Troy and Marc talk about the musical culture of New Orleans, growing up in the Treme, touring with Lenny Kravitz right out of high school, becoming the frontman of his own band, making the trombone a featured instrument, creating a musical education academy, and recording his new album, Lifted, which is inspired by his mother.

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Vanessa Bayer knows her comedic talent comes from a decidedly unfunny place. Vanessa's teenage cancer diagnosis focused her comedy skills, which in turn allowed her to help people process, understand and laugh at horrible things. Vanessa and Marc talk about how her natural optimism guided her through this health crisis and also put her in a great headspace for the Saturday Night Live audition process. Vanessa also explains why she incorporated her real life medical history into her new comedy series, I Love That For You.

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Children's book author Aaron Blabey can measure success by the more than 30 million books he's sold. But that success was a long time coming and in many ways felt like it was never in reach. Aaron tells Marc how the popular art and culture coming from outside Australia made him feel dissatisfied with his own life, how his excursions into acting and painting left him empty, and how he accidentally fulfilled all his creative impulses when he came up with The Bad Guys books. They also talk about The Bad Guys movie and what it was like to have Marc playing one of his characters.

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