If you thought Milwaukee Film‘s annual Milwaukee Film Festival was the nonprofit’s only cinematic bonanza of the year, THINK AGAIN.
Yes, Milwaukee Film’s third annual Dialogues Documentary Festival, presented by Potawatomi Casino Hotel, is set to light up the screens of the Downer and Oriental Theatres September 24-27. What’s DDF all about? Well, more than 30 documentaries and plenty of in-cinema conversations with visiting filmmakers and other special guests, that’s what.
“Our audiences love to immerse themselves in the true stories and contemporary conversations started by new documentaries, as evidenced by the documentaries that have won the Audience Award at past Milwaukee Film Festivals,” says Cara Ogburn, Milwaukee Film’s Artistic Director and lead documentary programmer, in a press release. “Milwaukee audiences are curious and deeply engaged, and we look forward to satiating that hunger for nonfiction storytelling with a great set of fresh documentaries at this year’s Dialogues Documentary Festival that are sure to inspire.”
All-access passes for the 2026 Dialogues Documentary Festival on sale NOW. (An early-bird discount is in effect through September 7.) Want a sneak peek of the fest? Check out a free-and-open-to-the-public Friends & Family Preview event Tuesday, September 8 at the Oriental Theatre. (Doors open at 6:30 p.m.; the program begins at 7 p.m.) Want a preview of the fest right now? Check out the first batch of films below, with blurbs courtesy of Milwaukee Film. (The complete lineup will be unveiled the week of August 31.)
Heavy Is The Crown (dir. Sean Kafer, 2026, USA)
Heavy Is The Crown follows charismatic Milwaukee community activist Vaun Mayes as he works alongside those most affected by cycles of violence, systemic neglect, and polarizing policing. Mayes reveals the resilience and care that sustain a community from within, empowering everyday community members to build programs and practices that nurture positivity in our city. The feature will be preceded by Dear Milwaukee, a short film made by youth at Arts@Large exploring similar themes and ideas.
Once Upon A Time In Harlem (dir. David Greaves, conceived by William Greaves, 2026, USA)
A decade after his death, genre-defying filmmaker William Greaves delivers a final surprise with Once Upon a Time In Harlem. Drawn from a 1972 gathering, the film unites surviving luminaries of the Harlem Renaissance (Arna Bontemps, Noble Sissle, James Ven Der Zee—to name a few) in electric conversations about art and legacy. Hailed as a “triumph” by The Hollywood Reporter and poised for awards season, this treasure offers a vivid, firsthand encounter with a movement that reshaped American history.
Sara Bareilles: Good Grief (dir. Josh Alexander, 2026, USA)
For the first time in seven years, Grammy-winning singer-songwriter Sara Bareilles returns to the studio with close friends to begin recording her most intimate album yet, born of profound personal loss and grief. This cinematic portrait observes the most private corners of Sara’s creative process, as well as her personal life. What unfolds in front of the camera is the incredibly raw experience of mining one’s own pain to create art—and the hope that carries an artist forward.
Time Warp (dir. Allison Berg, 2026, USA)
Fifty years after The Rocky Horror Picture Show became a queer rite of passage, the film’s message of “don’t dream it, be it” feels more potent than ever. In conservative Rock Springs, WY, 25-year-old Kenny Starling launches the town’s first drag and queer theater company, staging their own shadowcast of the cult classic. Time Warp follows Kenny and the determined troupe as they give themselves over to the absolute pleasure of chosen family and radical self-expression.
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