The film is a historical re-imagining that revisits the making of Shirley Clarke's 1967 documentary Portrait of Jason.

Director Stephen Winter was working on The Butler, his third film with Lee Daniels, when Sarah Schulman, renowned writer and activist, proposed that two of their mutual friends, performers Jack Waters and Bizzy Barefoot, had conceived a character based on Jason Holliday from the 1967 documentary Portrait of Jason by Shirley Clarke.

Mike Bailey Gates is an emerging video artist, photographer and fashion muse, perfect for the mysterious spirit "Billy-Boy."

And Tony Torn as racist DP "Saul" starred in the first play Winter saw in New York, "Tight Right White" by the legendary Reza Abdoh.

The only inspiration films Winter watched were Hitchcock's Psycho and The Trial by Orson Welles, both starring haunted gay icon Anthony Perkins.

Winter writes: I choose to shoot on S-VHS so the beauty and volatility of an antiquated format would mirror our subject's vintage intensity, but also to let go from the indie film "Tyranny-of-Video-Playback."

Scott of The New York Times described the film as "self-contained drama that feels like a documentary, and a historical re-enactment that seems to be happening in the present even as it offers astute commentary on the past.

For generations of queer men of color who have been horrified by Holliday's on-screen fate, Jason and Shirley offers a reinvention of a historical moment that sought to consign them to the roles of mascots and scapegoats.