From The Comic's Comic

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!

See Michael Cruz Kayne live onstage this week:

• Monday July 20 at The Bell House with other writers from The Late Show with Stephen Colbert
• Tuesday-Wednesday July 21-22 at Audible’s Minetta Lane Theatre with his new series, What Else, What Else. His guests will include Rosebud Baker, Tommy Brennan and Patti Harrison.

On May 19, he performed with Stephen Colbert and Paul Shaffer in his musical parody idea that had previously gotten rejected multiple times for The Late Show: It’s Raining Fish!

Here was the Tweet from 2019 when he marked the 10th anniversary of his son’s death with a thread about grief:

Here’s his January 2020 performance on Late Night with Seth Meyers:

For his Dropout taping, Michael Cruz Kayne talked a little bit about the process of making Sorry For Your Loss:

And here’s Stephen Colbert giving that “Colbert Bump” to his writer on April 3 to promote his Dropout special:

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