This week the legendary Judd Apatow returns to Working It Out for his fourth and best appearance yet. Judd tells behind-the-scenes stories from Bridesmaids and Funny People, as well as the most helpful filmmaking advice he’s gotten from other greats along the way. Judd and Mike also break apart the story of Judd’s first ayahuasca trip—and what that experience might have to do with both his parents’ divorce and his first sexual experience. Plus, jokes about how Judd somehow gained weight on Ozempic.

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In Chris Fleming’s recent Peacock stand-up special Hell, he calls out some audience members who are married and shouts, “This show is not for people who have wives. You have a wife?! Go see Mike Birbiglia!” Fleming is fearless about dragging the names of other comedians into his bits: from Bo Burham to Nikki Glaser to Bert Kreischer and more. Chris is a Massachusetts theater kid turned comedian and it manifests in stand-up comedy that is simultaneously avant-garde but also crowd pleasing. Mike and Chris sit down for a truly productive session of working out new material and they break down why Massachusetts is so darn repressed. Plus, they do no-holds-barred impressions of each other in what is one of the most unhinged episodes of Working it Out of all time.

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Mike welcomes Rory Scovel, whose special made Mike laugh so hard he spit water all over himself. Rory talks about how telling the truth and being vulnerable on stage led him to his best bits, how his taking up abstract painting is similar to comedy, and how a week of fully improvised stand-up shows gave Rory a new perspective on his career. Plus, the best and most off-the-rails “Working It Out” section the podcast has had yet.

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