The Winnipeg International Jewish Film Festival returns May 6 to May 23 with unforgettable stories on the big screen.

For 25 years, this festival has been about more than just films. It is about sitting together. It’s about laughing together. It’s about reflecting together. 

And it’s about experiencing stories that stay with you long after the credits roll.

This year’s lineup is filled with powerful documentaries, heartfelt dramas, and feel good comedies from around the world, along with special events that make every visit to the theatre something more.

Writer-director Matthew Shear stars as Sam, an anxious law school dropout who stumbles into a job babysitting his psychiatrist’s three granddaughters, and falls for the girls’ mother, Dianne, a once-promising actress in a rocky marriage. 

Sam agrees to babysit for the summer on Martha’s Vineyard, and he ends up in a house with the woman he pines for, her husband, the three kids, and all four grandparents, including his psychiatrist. 

In his directorial debut, Shear gives us a film that is both lighthearted and deeply real. An outstanding ensemble cast also includes Judd Hirsh, Amanda Peet, Bob Balaban, Jessica Harper, Holland Taylor, and Zosia Mamet.

This screening will be followed by an opening night reception.

Directors Matti Harari and Arik Lubetzki (Apples from the Desert) transform the beloved tales of Israeli writer Menahem Talmi into a cinematic mosaic pulsing with energy, wit, and nostalgia. This vibrant comedy focuses on the legendary Gang of Jaffa—unforgettable streetwise characters who talk fast, fight hard, and live by their own offbeat code. 

They may live on society’s edge, but their spirit, loyalty, and humour informs their lives, and it shines through every punchline and every heartbreak in the film. Jaffa Stories is a love letter to one of Israel’s most storied cities, and its people—a celebration of language, resilience, and the timeless art of storytelling.

In 2013 Israeli filmmaker Tom Shoval was casting for twins for his debut feature Youth. Among the auditionees was a pair of charismatic, non-professionals, identical twins Eitan and David Cunio, who won the lead roles.  Ten years later the Cunios were at their homes in Kibbutz Nir Oz when Hamas terrorists infiltrated. David, his wife, toddlers, and younger brother Ariel were taken hostage along with many others from the kibbutz- the hardest hit on October 7th. 

A distraught Shoval crafted A Letter to David, a cinematic letter to his friend whose fate was then unknown. Shoval uses unedited, behind-the-scenes footage and audition tapes from Youth, archival footage of the kibbutz, and present-day interviews with the Cunio family who fought tirelessly for the brothers’ release, to build a multi-layered documentary that explores the inexplicable connections between life and cinema, memory and reality and fraternal connection. 

When the film was released last year, David and Ariel were still being held in Gaza, and Shoval called Letter an unfinished film. Following their release in October 2025, Shoval added a new, longed-for happy ending.  A Letter to David The Complete Version is a cinematic experience not to be missed.

Benoît Poelvoorde (Man Bites Dog, The Brand New Testament) stars as Jean Chevalin, a bumbling trickster who accidentally deserts the army in 1940s France and must protect his family from the advancing Nazi threat. 

In a desperate bid for survival, he concocts a plan to pretend to be Jewish in order to receive help from smugglers to reach the free zone. 

This inane and misguided plan throws his family into the heart of the Resistance – and into a chaotic journey filled with danger, unexpected heroism, and personal transformation.  A surprising but hilarious and heartwarming new WWII comedy.

Throughout decades of prejudice hampering the integration of Jewish immigrants in America, the Borscht Belt in New York’s Catskills provided an oasis of belonging. Grossinger’s Resort was at the centre of it all, providing a physical and mental getaway where Jews—and others from marginalized communities—needing a break from the city could relax. 

Over the years this real-life inspiration for Dirty Dancing attracted a who’s who of comedy, as well as political and athletic figures.  

In her high spirited and comprehensive documentary, Eiselt resurrects this vanished world with an immersive warmth, while providing a timely reminder of the historic richness of Jewish culture and its immeasurable contributions to American life.