Mike welcomes back comedian Gary Simons, who, since his last appearance on the podcast, opened for Mike on his latest tour, had a few of his stand-up bits go viral, and has been performing at the Comedy Cellar. Now, Mike and Gary answer listener questions from people who have taken the leap into stand-up comedy and are looking for advice about how to continue. They discuss open mics, bombing, pre-show mantras, and more.

This week PDD returns to the podcast a year and a half after originally coming on. Since then, Mike and the boys have started a monthly improv show called “Please Don’t Birbiglia” at UCB. The group talks about what it’s like to improvise together, the unsparing roasts PDD did of Mike when they opened for his show "The Good Life," and the creation of PDD’s Jon Hamm pizza sketch—from Monday’s pitch in Lorne’s office to airing live on SNL. Plus, the unlikely thing that shows up in more than one PDD member’s Instagram algorithm.

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Ira Glass has appeared on the Working It Out podcast three times before, and usually it’s Mike asking Ira for advice, whether it’s about podcasting or storytelling. But now the tables have turned: Ira recently listened to a stand-up set he performed years ago, he has the itch to try it again, so he’s come to Mike for comedy advice. On this episode, Mike and Ira listen to Ira’s old stand-up set in real time, break down what worked and what didn’t, and brainstorm ideas for Ira’s next set.

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Zarna Garg first appeared on the Working It Out podcast in 2022 and since then her popularity has continued to rise. Zarna explains to Mike how she has built her comedy career like a business, and why performing for an audience of one or two is no different for her than performing for an audience of thousands. Mike and Zarna discuss free speech in Zarna’s native India, and what it’s like for her to raise her kids in America. Plus: why no one in Zarna’s family has been allowed to read her memoir This American Woman.

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After decades of being a beloved comedian’s comedian Jessica Kirson has broken out in the last few years with viral crowd work videos and a brilliant new special on Hulu called “I’m The Man.” Mike and Jessica dig deep into the nuts and bolts and emotional work of being a stand-up comic, including overcoming stage fright and dealing with hecklers. Jessica breaks down the difference between her on stage and off stage personas, and recalls her childhood which was spent listening in, with her stepbrother Zach Braff, on her therapist mother’s sessions. Plus, Mike has an awkward experience in a steam room and Jessica tells the story of when she put a heckler up against a wall.

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This week 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.

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Rachel Feinstein recently appeared as a surprise guest on one of Mike’s shows at the Beacon Theatre, where Mike observed after the show that everything Rachel said in the green room could be a bit. Now, on the heels of her Netflix special Big Guy, and in her third appearance on Working It Out, Rachel spills all the details about living with other comedians, the time she moved in with a Bengali family she met on a bus, and all the red flags she ignored in her previous relationships. Plus, Mike shares an unflattering movie offer he received and Rachel defends her pre-schooler’s permanent record.

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This week Andrew Schulz comes on the podcast and Mike and Andrew break apart why the two of them are unlikely work friends. They discuss Andrew having Donald Trump on his podcast, Andrew’s new deeply personal Netflix special, “Life,” and the politics of free speech in comedy. Plus, Andrew reveals the guest he regrets having on his podcast, “Flagrant.”

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