Ray Romano: Sometimes the Setup is the Punchline

(Recorded May 2023) Ray Romano has an iconic sitcom and a celebrated stand-up career under his belt, so what drives him to keep challenging himself artistically? Mike and Ray, who often follow each other at the Comedy Cellar, ponder the complicated answer to that question. Plus, discussion of comedy craft, joke-writing technique, and the two separate times Ray was held up at gunpoint.

Rosebud Baker’s first appearance on Working It Out was in 2021. Since then she’s become a writer on SNL, written for That Damn Michael Che, and become a parent. Now Rosebud returns to talk with Mike about how being a parent affects comedy, and they dispel certain attitudes about filming a comedy special while pregnant. Plus, the art of pitching ideas for different types of sketch shows, and why Rosebud’s daughter has to call her grandfather “Mr. Baker.”

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John Early, recently nominated for an Emmy and a Critics Choice Award, sits down with Mike for the first time since the two of them appeared as brothers in Taylor Swift’s, “Anti-Hero” music video. The two discuss avant-garde comedy, Brittany Spears impressions, and what it means to express earnest despair in John’s new Max special, “Now More Than Ever.” Plus, the time John ran away after coming out to his best friend.

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We’ve created an episode for all of you making long car trips or taking long jogs or stretching out on your long beloved couch. It’s our best moments of 2023 episode! It includes Ray Romano’s take on marriage, a joke from Ramy Youssef’s funniest uncle, Rachel Feinstein’s pitch perfect impression of her husband, and deep confessional moments about Mike’s friendships with Tom Papa and Gary Gulman. Plus, Ira Glass’s diagnosis to not just work out Mike’s jokes but to work out Mike’s life.

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Working It Out will be back on January 1. This week, we’re sharing an episode of The Sarah Silverman Podcast, from our friends at Lemonada Media.

Sarah hates men’s cologne and wants you to STOP. IT. Plus, she offers advice on setting ground rules for a threesome, reacts to a child who’s obsessed with her hooky-ass song, “Night Bra,” and recounts a special moment on stage with her sister, Laura.

To hear more of Sarah’s show, head to https://lemonada.lnk.to/sarahsilverman

Mike welcomes back to the podcast comedian Beth Stelling, whose Netflix special If You Didn’t Want Me Then is on seemingly everyone’s best of year lists, including Mike’s. Mike and Beth discuss touring together, Beth’s desire to be authentic on stage, and Beth’s dad feeding raccoons out of a trough. Plus, they explore the parallels between stand-up comedy and Beth’s new venture: professional field hockey.

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Jimmy Carr is one of the most successful comedians in the entire world. On the heels of playing Carnegie Hall and heading out to hundreds of concert dates across many continents, Jimmy Carr returns for another episode of Working it Out. Jimmy and Mike discuss the benefits and pitfalls of dark humor, what Jimmy discovered from several public cancellations, and why sometimes the goal is simply to get better than you were last year. Plus, what ever happened to ordering just a slice of pizza?

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Mike welcomes back three-peat guest Joe Birbiglia to celebrate the premiere of Mike’s new Netflix comedy special The Old Man and the Pool. Mike and Joe discuss the four year development of the show, share memories about the Worcester, Massachusetts YMCA pool, and share the funniest jokes that didn’t make it into the special. *Should* they have made it into the special? Joe thinks so. You be the judge. Plus, Mike answers listeners’ questions about the special.

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Mike’s new special, “The Old Man & The Pool” is finally on Netflix and he brings on an all-timer to celebrate. Pete Holmes returns for a third Working it Out, and he and Mike roast each other as hard as only old friends can. Mike and Pete discuss Pete’s new Netflix special “I Am Not For Everyone,” the problem with Micheal Jackson’s nickname “Wacko Jacko,” and what secrets Pete has in store for his next hour of comedy. Plus, Pete literally won’t stop doing impressions: Bill Burr, Jerry Seinfeld, John Mulaney, and of course, Mike.

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Jo Firestone joins Mike for her second appearance on Working it Out. In addition to just being named the head writer of the newest late night show on network TV, Jo just published a comedic murder mystery called “Murder on Sex Island” and proclaims she is *nothing* like the book’s protagonist even though the similarities are striking. Jo also explains why there’s so much dust in her purse, and posits that the scariest part of haunted houses aren’t actually the jump scares, but rather the promise of nudity.

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