Director-for-a-day Todd Winkler choked back tears talking about working with two Oscar-nominated screenwriters, two acclaimed actors and a cinematographer of renown inside San Quentin Rehabilitation Center to help shoot a scene he, a man incarcerated there, wrote.
“It’s a really emotional day,” Winkler said, admitting to being a bit overwhelmed on Feb. 24, having spent the day in the director’s chair shepherding actors Simon Rex and Sean San José through a comedic scene he wrote.
Seeing his words interpreted by pros and witnessing the scene get shot on 16mm film, assisted by a crack crew, is somewhat of a dream come true for the writer, even if he prefers dabbling in dystopian short fiction over comedy.
Winkler’s piece being shot during the day-long workshop, the first of its kind a San Quentin, was the winning entry in a pitch-screenplay contest.
The workshop was spearheaded by “Sing Sing” director/co-screenwriter Greg Kwedar and collaborator Clint Bentley, who cowrote and produced “Sing Sing” and directed the Sundance Film Festival award- winner “Train Dreams,” which is being released on Netflix this year.
Winkler isn’t alone in considering the workshop shoot as something special.
“There weren’t any walls these days,” said Kwedar when the shoot wrapped.
Bentley considered the day one of the most fun shoots he’s ever worked on, praising the actors, writing and camerawork: “There are a number of those things that would be amazing on a film set anywhere. I hope you feel very proud of yourselves.”
Winkler was pleased to notice that Rex (a former Alameda resident who starred in “Red Rocket” and appears in the upcoming “Operation Taco Gary’s”) arrived on the set (just outside the San Quentin Media Center) so prepared, even flashing a marked-up version of his screenplay. Rex jotted down notes to better inform his character, a frustrated, taken-with-himself actor who feuds with a persistent director (San José) who has a different vision of how a particular scene should play.
Seeing Rex take the role so seriously moved Winkler so much he had to tell him, “When you pulled my script out of your pocket and it had all these notes over it, I said ‘Oh my God…’” before tearing up, unable to complete his thoughts.
“Oh, that’s beautiful,” Rex responded. “Thank you, man.”
There were many people to thank for making the day a reality, including the Kwedar, Bentley and San José, the local theater dynamo who costarred with Oscar-nominated Colman Domingo in 2023’s acclaimed film “Sing Sing,” which highlighted how the Rehabilitation Through the Arts program helped the men at the New York correctional facility.
Others who played vital roles: San Quentin Film Festival founders Cori Thomas, a playwright and actor, and Rahsaan “New York” Thomas (no relation), a writer, director, social justice activist and a Pulitzer Prize finalist who was incarcerated at San Quentin; cinematographer Amy Vincent (“Eve’s Bayou”); Workshop’s Partners Kodka, Ethos, Be Forward Productions, Panavision and the studio A24, which released “Sing Sing.” Producers Scott Budnick (“The Hangover”) and Madison O’Leary (“On These Grounds”) also played key parts.

The idea for the filmmaking workshop germinated during a talk Kwedar had with Ryan Pang—an avid and inquisitive cinematography fan who subscribes to American Cinematographer — during the San Quentin Film Festival in 2024. Pang’s narrative short “Paranormal Patrol” was in a lineup at that historic event, which drew Bentley, Kerry Washington (Netflix’s “Daughters”), W. Kamau Bell, Cord Jefferson (“American Fiction”) and others interested in works created by the men incarcerated there or filmmakers who had been incarcerated.
Kwedar and Pang struck up a conversation and Pang asked a slew of questions about making “Sing Sing.” His focus and curiosity were the sparks to fire up interest.
“Art works best when it’s an exchange… when we are leaning in and we all have something to learn and something to teach. I think that’s what’s so special about creating with everyone today,” Kwedar said at the wrap.
Earlier in the day, Pang, a huge fan of cinematographer Vincent, asked her to autograph a copy of American Cinematographer magazine.
Vincent, impressed by Pang and others on the shoot, said, “Everybody who got behind the camera, I felt like your life changed just a little bit back there. I sincerely hope I get to work with you guys again and take all your skills just a little bit further. I really appreciate the focus and the concentration.”
San José summed up most everyone’s sentiments, saying, “Let’s keep on doing it.”
Submissions are open for the 2025 San Quentin Film Festival, slated for Oct. 23-24. Warden Chance Andes also has approved the festival broadening its scope with SQFF Presents, a year-round program set to bring more screenings, filmmakers and master classes to San Quentin residents.
The festival complements San Quentin’s dynamic media center, which features a vibrant monthly newspaper produced and written by the men there, along with podcasts and other programs.
Winkler was moved that the movie professionals took the time to come to San Quentin, lend their expertise and see the talent behind the walls: “We’re in prison,” he said. “We don’t want to be here…But all these outside people come in and seem to really care…No one’s getting paid to film my story and get it on film.”
For more information about the festival, visit https://www.sanquentinfilmfestival.com/.
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