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.

• The 99 Year Old Man Movie Trailer
• The 99 Year Old Man on IMDb

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Harry and Daniel are joined by writer Leigh Stein, author of the novel If You’re Seeing This, It’s Meant for You, to unpack the ambition, anxiety, and Jewish bravado pulsing through Marty Supreme, directed by Josh Safdie.

Rather than simply treating the film as a sports drama, the conversation zeroes in on Marty as a driven artist figure — obsessive, self-mythologizing, hungry for greatness, and constantly performing his own legend. What does it mean to chase excellence not just as an athlete, but as a Jew carrying history, insecurity, and defiant pride on his back (and sometimes around his neck)?

Leigh brings her sharp cultural lens to questions of ego, survival, and spectacle — including Marty’s provocative swagger and the ever-lingering communal anxiety: Is this good for the Jews? Is Marty a symbol of resilience, a caricature of excess, or both at once?

It’s a lively, searching conversation about ambition, representation, and the thin line between self-invention and self-delusion — with plenty of ping-pong metaphors along the way.

Marty Supreme Movie Trailer

Marty Supreme on IMDb

Leigh's Links

• If You’re Seeing This, It’s Meant for You
• Leigh Stein on Instagram
• Leigh Stein on Substack

Connect with Jews on Film online:

• Jews on Film Merch - https://jews-on-film.printify.me/products
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Harry and Daniel dive into the swashbuckling fairy tale classic The Princess Bride with filmmaker and special guest Michael Lukk Litwak, director of Molli and Max in the Future.

Directed by Rob Reiner and written by legendary screenwriter William Goldman (adapting his own novel), The Princess Bride is a story of fencing, fighting, torture, revenge, giants, monsters, chases, escapes, true love—and, yes, miracles. But it’s also something more: a distinctly Jewish-inflected fairy tale wrapped in the rhythms of a grandfather’s bedtime story.

Harry, Daniel, and Michael explore Goldman’s wry, self-aware storytelling voice, Reiner’s humanistic direction, and how the film balances sincerity and satire without ever winking too hard. They unpack Mandy Patinkin’s unforgettable turn as Inigo Montoya, the comedic brilliance of Wallace Shawn and Billy Crystal, and the film’s surprising emotional depth beneath all the quotable lines.

Together, they ask: What makes this fairy tale feel so grounded? How does Jewish humor shape the film’s tone? And why has The Princess Bride endured as a generational touchstone for audiences who can quote it line for line?

As you wish… it’s an episode about storytelling, myth-making, and why true love (and a good screenplay) conquers all.

• The Princess Bride Trailer
• The Princess Bride in IMDB

Michael's Links

• Follow Michael on Instagram
• Watch Molli and Max in the Future

Connect with Jews on Film online:

• Jews on Film Merch - https://jews-on-film.printify.me/products
• Instagram - https://www.instagram.com/jewsonfilm/
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• YouTube - https://www.youtube.com/@jewsonfilm
• TikTok - https://www.tiktok.com/@jewsonfilmpod