Interviews | "Making Sense of Humor" Documentary

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Listen to my in-depth conversation with the great Craig Kilborn, former host of The Daily Show and The Late Late Show. We discuss his remarkable career and how he’s harnessed humor as both art and perspective. We also talk about his evolution in television, the subtlety of his comedic voice, and how everyday humor can unite, comfort, and connect us all. This interview and the others, are  part of my larger documentary, Making Sense of Humor.

Here, I have an insightful conversation with Brian Kiley, a two-time Emmy- award-winning comedian and longtime writer for Conan. For 27 years, Kiley helped define late-night comedy, earning 16 Emmy nominations and two wins.  We discuss his decades in comedy, his approach to writing for television, and how humor connects people at their most human level. From late-night punchlines to moments of quiet laughter, Kiley shares what makes great comedy timeless, uniting, and deeply meaningful. This interview is part of my larger documentary, Making Sense of Humor.

Listen to my conversation with Preet Bharara, former U.S. Attorney for the Southern District of New York and Host of Stay Tuned with Preet. We explore  how humor functions in his life as well as places like the law, politics, and public life. This interview is part of my larger documentary, Making Sense of Humor.

Check out my conversation with Jessica Pisano, Professor of Politics at The New School and an expert on authoritarianism, propaganda, and the politics of humor with a focus on Russia and Eurasia. We discuss how Volodymyr Zelensky, a former comedian turned president, has harnessed humor as a form of leadership and resilience in Ukraine. Pisano explains how his authenticity, timing, and warmth have helped forge national unity, disarm fear, and connect deeply with a population under extraordinary strain. This interview is part of my larger documentary, Making Sense of Humor.

Here, I have a conversation with David Litt, former Senior Speechwriter & Comedy Writer for President Barack Obama. We dive into how Litt helped shape Obama’s sharp, witty public voice, from White House Correspondents’ Dinners to viral speeches. He shares insights into crafting political comedy. This interview is part of my larger documentary, Making Sense of Humor.

I also interviewed  Richard Carwardine, one of the world’s leading Abraham Lincoln scholars and former President of Corpus Christi College, Oxford. Author of several acclaimed books on Abraham Lincoln, including "Lincoln: A Life of Purpose and Power" and "Lincoln’s Sense of Humor," Carwardine offers some good insight into the role humor played in Lincoln’s leadership. We discuss Lincoln’s incredible ability to disarm tension through wit, his gift for self-deprecation, and the funny, deeply human stories that reveal how laughter helped him endure the Civil War and connect with the American people. This interview is part of my larger documentary, Making Sense of Humor.