Stephen Winter is an award-winning filmmaker known for writing and directing “Jason and Shirley” and “Chocolate Babies.” In 2023 Stephen directed “The Space Within” the number one fiction podcast for Audible, produced and starring Jessica Chastain.
CHOCOLATE BABIES Q&A: Stephen Winter and Jeremy O. Harris
STEPHEN WINTER
DIRECTOR, PRODUCER, WRITER
Stephen Winter is an award-winning New York independent filmmaker and writer living in New York City for over 30 years. His 1996 debut feature film Chocolate Babies was restored by UCLA/Outfest in 2021; twice featured on the Criterion Channel and since been cited in multiple “best-of” lists including Indiewire. In 2004, Stephen produced Jonathan Caouette’s landmark “narci-cinema” documentary Tarnation (Wellspring), with executive producers Gus Van Sant and John Cameron Mitchell, (Sundance, Cannes, NYFF, Roger Ebert’s Overlooked Film Festival and AFI’s “Most Significant Moments”). Stephen was story editor on How To Survive A Plague (2012), produced by Howard Gertler (Academy Award nominee Best Feature Documentary), and The Death and Life of Marsha P. Johnson (2015).
Stephen’s second feature film as writer and director Jason and Shirley (2015) starring and co-written by Sarah Schulman and Jack Waters, premiered at BAMCinemaFest and played for two weeks at the Museum of Modern Art. Richard Brody called it “one of the year’s best” (The New Yorker). The new edition of the film Jason and Shirley Revisited premiered at NewFest in 2025 for a 2026 roadshow in theaters.
In podcasts, Stephen directed and co-created with Tristan Cowen the cult sci-fi comedy horror fiction series Adventures In New America for the Night Vale Network. (“The Best New Social Thriller is a Podcast,” New York Times, Sep. 13, 2018). Stephen co-wrote Sound Barrier: Sylvester, a Spotify original documentary series hosted by USC Thornton Dean Jason King, selected as one of The Guardian’s picks of the week for best podcasts on untold life stories. For Audible and Topic Studios, Stephen is director of season one and two of the sci-fi drama podcast The Space Within (2023-26), written by Josh Fagin and Greg O’Connor, starring and co-produced by Oscar winner Jessica Chastain, featuring Michael Shannon, Michael Stuhlbarg, Bobby Cannavale, Carmen Ejogo, Mandy Patinkin, Jay O. Sanders, Jessica Hecht, Karen Allen and Ellen Burstyn.
In 2025 Stephen began directing A Brief History of Silence: Marlon James Rewrites Jamaica’s Story – And His Own, a feature documentary about the history and future of LGBTQIA human rights in the island nation of Jamaica starring Booker award winning author Marlon James, who also serves as executive producer. Initial funding for the film was provided by The Ford Foundation and production will continue into 2026.
Stephen’s three 1991-1992 cover photos for the legendary Chicago-based house music publication THING MAGAZINE (She Knows Who She Is) edited by Robert Ford, was included in the Brooklyn Museum’s exhibition Copy Machine Manifestos: Artists Who Make Zines in 2023 and its catalogue (Phaidon) with essays by Tavia Nyong’o, Julia Bryan Wilson, Mimi Thi Nguyen, and others. These photos were shot while Stephen was active in ACT-UP Chicago, where he was mentored by activist Ortez Alderson and filmmaker Marlon Riggs.
Stephen has worked on films with Allan Hughes, Xan Cassavetes, John Cameron Mitchell, Jim Lyons, David France, Soledad O’Brien; and director Lee Daniels on multiple projects including Precious (2009), The Paperboy (2012 and The Butler (2013).
Stephen directed music videos for M. Lamar, Cheese on Bread, The Illustrious Blacks, Breakaway, and, of Montreal. Playwright Jeremy O. Harris has called Stephen “The father of modern Black Queer cinema.”
NEWS
December 2025
Chocolate Babies free community screening at Grand Lake Theatre for World AIDS day with Gilead and Frameline
October 10, 2025
Jason and Shirley Revisited, a new edit of Stephen’s 2015 feature, screened at Brooklyn Academy of Music as part of Newfest
March 1, 2024
Stephen is featured in the magazine BODYELECTRIC, interviewed by Jordan Firstman
Summer 2023
Winters-helmed Space Within premieres on Audible.
July 13, 2022
Stephen Winter was head writer on the Spotify podcast series, Sound Barrier: Sylvester.
SOUND BARRIER: SYLVESTER - episode 4 “Giant Step”
Available now