For their 100th (give or take) episode, Harry and Daniel celebrate a major milestone by revisiting where it all began—with their very first guest, Yuli Masinovsky. Together, they keep things loose, reflective, and a little bit meta as they dive into The 99 Year Old Man, the documentary from Judd Apatow chronicling the life and legacy of Mel Brooks.

Along the way, the trio looks back on four years of podcasting—how the show has evolved from plot-heavy breakdowns to more thematic, free-flowing conversations—and what it means to build a creative project over time while balancing careers, families, and life changes. They revisit early Jews on Film staples like “the stretch,” the IMDb summary, and the ever-elusive perfect format.

On the film side, the conversation explores Brooks as both a comedic pioneer and a complicated cultural figure: his role in shaping Jewish-American humor, his connection to figures like Sid Caesar, and the lineage of comedy that runs from the Borscht Belt to today. The group also digs into the documentary itself—its length, structure, and whether it reveals anything new about a performer who’s always “on.”

Most provocatively, the episode wrestles with questions of Jewish identity in Brooks’ work: Is his humor a bridge to mainstream audiences or a performance for an in-group? Does the film sidestep deeper explorations of Judaism in favor of persona and mythmaking? And what does it mean for a Jewish artist to both embrace and satirize his own identity?

It’s a celebratory, thoughtful, and occasionally heated conversation about comedy, legacy, assimilation, and storytelling—plus a few looks ahead to the next 100 episodes.

Mazel tov to Jews on Film… and here’s to 100 more.

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