Episode #500: Michael Cruz Kayne

Michael Cruz Kayne is a comedian, actor and writer based in NYC. He wrote for the last six seasons of The Late Show with Stephen Colbert, where he’s an Emmy nominee again in 2026. At the Upright Citizens Brigade Theatre, he co-wrote and starred in Terrible Babysitters, a 2013 webseries with D’Arcy Carden, and directed Josh Sharp and Aaron Jackson in their two-person musical, Fucking Identical Twins, which ultimately became the 2023 feature film, Dicks: The Musical. You may have seen Michael Cruz Kayne in a supporting role on Severance, or seen him tell jokes on Late Night with Seth Meyers. Ten years after one of his sons died shortly after childbirth, he went viral on Twitter writing about how he realized a decade later he needed to talk about his grief all the time — that ultimately led to an off-Broadway run with Audible for what became Sorry For Your Loss, released as a comedy special on Dropout in March 2026. Michael Cruz Kayne sat down with me over Zoom this past week to talk about his life and career and what comes next, even if the heat wave fried our Zoom in the process. There’s a lot to get to, so let’s get to it!