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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