Questlove: The Art of Self-Sabotage

Comedian Caleb Hearon just turned 30 and he’s already got an hour-long HBO special, hosts a hit podcast (So True with Caleb Hearon), and  was named one of the top social media influencers of 2025 by Rolling Stone. But it hasn’t been an easy road. Caleb talks with Mike about his battles with suicidal ideation, how improv comedy saved his life, and how he drew on the passing of his estranged father for his comedy special. Plus, Caleb and Mike discuss the value seeing stand-up live vs. on TV, and come up with a plan to go off the grid and live in a cabin in the mountains together.Please consider donating to KC Tenants Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

The great Jenny Slate joins Mike this week for a wide-ranging conversation about getting hypnotized after being fired from SNL, a graduation speech Jenny gave to a class of one person, and making art to feel less lonely. Plus, jokes and stories about seeing your friends naked, improv classes for the elderly, and the time Jenny’s faked case of appendicitis went too far.Please consider donating to NPR Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Best of WIO: Questlove(Recorded April 2025) The legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as The Roots. Plus, what it was like accepting an Oscar after The Slap and the behind-the-scenes process of Quest’s new documentaries Sly Lives! and Ladies & Gentlemen... 50 Years of SNL Music.Please consider donating to: The Food and Finance High School Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This week the one and only Sebastian Maniscalco sits down with Mike for a wide ranging conversation on their parenting strengths and weaknesses, the difference in what makes them cry, and Sebastian’s early days waiting on his future co-star Robert DeNiro. Plus, Sebastian reveals if he ever acts like Sebastian offstage. Please Consider Donating To: Tag, You're It! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This week Mike sits down with Julio Torres to talk comedy writing and color theories. Based on ideas posited in Julio’s new Off-Broadway solo show, Color Theories, the two of them get to the bottom of what color Barbie the Movie, Martha Stewart, and Jeremy Strong are. They also discuss the behind-the-scenes story of Julio’s viral SNL sketch, “Papyrus” starring Ryan Gosling. Plus, two encounters Julio and Mike had at the gym that aren’t sitting right with them. Please consider donating to: GLITS Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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Comedian and SNL writer KC Shornima might be the only Working It Out guest who has climbed Mount Kilimanjaro. KC and Mike get to the bottom of why she thrives in stressful situations like mountain climbing, camping on a glacier, and writing for Weekend Update. Mike asks KC some questions from her bosses, Michael Che and Colin Jost, and KC explains why she feels compelled to talk about difficult topics on stage.Please note: This episode contains discussion of sexual assault.Please consider donating to Theatre 202 Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Three years ago, comedian Ryan Hamilton was hit by an airport shuttle bus. Two years ago, Ryan came on Working It Out to talk about the experience. Now, he returns to explain how he learned to talk about the traumatic event on stage and find the humor in the pain, which included buying weed with his mom during his recovery. Ryan also breaks down the daily routine of touring with Jerry Seinfeld, and shares the blunt advice he got from Chris Rock.See Ryan Hamilton's special taping at the Neptune Theatre in Seattle on October 4. Get tickets here.Please consider donating to Scott Hamilton CARES Foundation Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

(Recorded January 2025) Mike sits down with Severance’s very own Ben Stiller and Adam Scott. The three of them dig into the behind the scenes of Severance Season 2 and discuss what it is that makes them work so well together as actor and director.  Ben and Adam share audition advice for actors, as well as how their grieving processes influenced their work together. Plus, Mike and Adam nerd out about The Ben Stiller Show and Reality Bites, and Mike reveals which Severance character he almost played.Please Consider Donating To: The Center for Reproductive Rights and the UNHCR Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Fresh off a few gigs featuring on John Mulaney’s new tour, Mike and Fred sit down for his first in-studio appearance on Working it Out. They discuss Fred’s SNL audition, his best sketch writing advice, and the manners of navigating video exhibits in museums. Plus, Fred borrows Mike’s guitar to demonstrate how cultures around the world play the acoustic guitar. Please consider donating to: Letters Charity Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.