Hamilton director Thomas Kail is back for round two and he usually makes me cry at the end of the episode, but this time he's switching it up and doing it at the top of the second episode. But don't worry, I deflect and change the subject pretty quickly! Whew!

Tommy is as thoughtful as he is honest, so while he talks about the power of live theatre and offers insight into how and why he works the way he does, he also asks the questions that permeate almost every single project he works on: How much time do I have? And what do I do with my time? Those questions, and the fact that he takes such amazing care of the audience (regardless of the medium) are two of the reasons why I'm so honored he took the time to record with me again, almost seven years after his first visit to the pod. I've said it a million times on this podcast, but I'll say it again because it's true: if you want to truly be seen and heard, have a conversation with Thomas Kail.

And yes, we also laugh a lot and have fun! Tommy talks about his kids, It's a Wonderful Life, upcoming projects (live action Moana!), and why he's never leaving New York City. It's all about balance, mostly because "sometimes you're the Tommy, and sometimes you're the Lin."

This episode was recorded in November of 2025 at WTF Media Studios in Manhattan and produced with Natalie Grillo from Any Moment Productions in collaboration with Meghan Miles.

#124: Thomas Kail // Part One (2018)

#125: Thomas Kail // Part Two (2018)

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#498: Thomas Kail Returns! // Part Two