Joy, Grief, and the Power of Humor with Allen Klein

Is it possible to laugh in a hospital room?
To feel joy in the middle of grief?

I first reached out to Allen Klein after seeing a post about a new documentary being made about his life. The film — The Jollytologist, directed by Sky Bergman — immediately caught my attention.

I’ve long admired Sky’s previous films, and when I saw that she was telling Allen’s story — a story about choosing humor and playfulness even in the hardest seasons — I knew I wanted to talk to both of them about this project. I instantly saw a connection between Allen’s life work around grief and humor and my own ongoing inquiry into how to be more playful in life.

Before Allen and I recorded this conversation, I had the chance to see a sneak peek of the documentary. I loved it. It made me laugh. It made me cry. And it deepened my appreciation for the philosophy Allen has lived — not just taught — for decades.

Allen’s life story holds both heartbreak and levity. After his wife’s three-year battle with a rare liver disease, he found himself navigating profound grief while raising their 10-year-old daughter. Hospital rooms became part of daily life. And yet, in the midst of all that uncertainty, something unexpected kept showing up.

Laughter.

Not because the situation wasn’t serious.
Not because the loss wasn’t devastating.
But because joy can sometimes coexist with sorrow in surprising ways.

In our conversation, we explore that tension — how humor can offer relief without denying reality. We talk about rejection and redirection (including the moment he was kicked out of Yale Drama School), the power of perspective, and why playfulness isn’t naïve… it’s resilient.

Next week, I’ll be sharing a companion episode with Sky Bergman about the making of the documentary and why Allen’s story feels especially relevant right now. There will also be an opportunity to register for an upcoming online screening before the film heads to festivals — and I’ll share those details as soon as they’re available.

If you’ve ever wondered whether it’s okay to laugh during grief… or how to stay open and playful when life feels heavy… I think this conversation will stay with you.