Josh Gondelman is a writer and comedian who currently writes and produces comedy for Desus and Mero on Showtime. Before that, Gondelman spent five years at HBO’s Last Week Tonight with John Oliver, earning multiple Emmys and other awards for his work on the writing staff. Much before that, before his comedy career took off, he taught preschool in the Boston area. As a performer, you’ve seen him tell jokes on Conan, The Late Late Show with James Corden, and Late Night With Seth Meyers, or heard him on one of his three comedy albums. As a writer, his work also has appeared in McSweeney’s, New York Magazine, The New Yorker, the Modern Seinfeld parody Twitter account, and more. His book of essays, “Nice Try: Stories of Best Intentions and Mixed Results,” is out now. So let’s get to it!

Jim and Jeannie Gaffigan have survived and thrived in ways they couldn’t have imagined when they pulled the plug on their TV Land series in the summer of 2016. Within months, Jeannie was diagnosed with a life-threatening brain tumor, and the couple, who have five young children, wondered what would happen next. Jeannie writes about all of that in her new book, “When Life Gives You Pears: The Healing Power of Family, Faith, and Funny People.” Jim, meanwhile, was nominated for Grammy Awards in both 2018 and 2019. And in August 2019, Gaffigan became the first stand-up comedian to launch a special with Amazon Prime Video as an Amazon Original with “Quality Time.” Jim and Jeannie gave me some quality time in their New York City apartment to talk about everything they’ve been through together, so let’s get to it!

Evan Shapiro had run cable TV stations IFC, Sundance Channel, and Pivot before he launched Seeso, a streaming comedy service owned by Comcast and NBCUniversal in 2016. Shapiro went independent for a couple of years after that, but in May 2019, he took the reins as president of the National Lampoon, where he’s in charge of all development, acquisitions, and production on television, digital and audio content for the entertainment company. Shapiro helped rebrand the Independent Film Channel as a home for celebrated comedy in IFC, and brought podcasters to TV with Comedy Bang! Bang! and Maron. What can he do to revitalize the National Lampoon brand? He’s already working with the Forever Dog podcast network to develop some of their shows for TV. Shapiro, who also teaches TV at NYU, invited me to his unconventional offices at Soho House to give us a crash course in what’s happening with comedy these days. So let’s get to it!