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Jason and Shirley to premiere at MoMA 

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Photo by Ricardo Nelson

It’s hard to distinguish whether Stephen Winter’s film Jason And Shirley is a form of reality or fiction.

Upon first glance, Jason And Shirley—which premieres October 20 at the Museum of Modern Art—comes across like a relic. There's a sense that it’s an old video footage waiting to be revisited. 

Through explosive cinematography, Winter explores Shirley Clarke, “Jewish, wealthy, an Oscar-winner and a rare female film director of her era to gain national prominence,” and her relationship with Jason Holliday, “a fabulous but downtrodden black, gay, middle-aged hustler and cabaret performer whose life revolves around sex, jazz and narcotics who was known throughout New York’s pre-Stonewall gay world and jazz world as the hottest mess around.”

The product is a mesmerizing depiction of two people many New Yorkers still recall being friends with. Yet for those unfamiliar with Holliday or Clarke (and her 1967 experimental documentary Portrait of Jason), then the film leaves people wondering whether they've watched old video footage, and it is in fact a fictional retelling of a true-to-life story. 

The original film was made in 1966 over an intense 12-hour marathon filming session where Jason told his stories of racism, homophobia, abuse, and prostitution to Shirley at the Chelsea Hotel in New York City. 

Jonas Mekas, coined as “The Godfather of American Avant-Garde Cinema,” was a close friend, confidante, and colleague of Shirley Clarke. He knew her and Jason well and jaw struck by the lifelikeness to the film. 

"I heard about this film and I wanted to see it but was afraid to because I knew all the protagonists semi fictionalized in this film, so I would still see the living persons, my old friends, so well in my memory. And that is why I was surprised and amazed at the amazing job Jack Waters did, and Stephen Winter. Jack’s recreation of Jason is so amazingly true I thought I was back in Shirley’s apartment watching Jason and Shirley. The face, the movements, the character was so truly Jason. The portrayal of Shirley Clarke is true to life. And Carl Lee also comes in essence.” 

Director Stephen Winter immaculately mixes fantasy and reality with electric performances from artist Jack Waters and writer Sarah Schulman in the title roles (who both co-wrote the film with Winters). 

In his director's statement, Winter addresses how working on Lee Daniels' The Butler facilitated the making of this film:

"For work on Lee Daniels’ The Butler I had viewed and catalogued countless Civil Rights news footage, radio broadcasts, images and speeches, the turbulent era Portrait of Jason was set. And, as a biracial black and Jewish-descended queer gay man, my attraction/repulsion of the 'performance' Shirley Clarke captured of Jason Holliday alone as 'himself' had always been an enthralling embarrassment. An astonishing showcase of self loathing for Jason to drink himself staggering, smoke his lungs black, over-share failures, catalogue broken dreams, mocked by off-screen voices, then shatter into (crocodile?) tears... What was the ultimate purpose of this? To show no one should trust or find affection for the black gay man? That the homosexual African-American exists on the weakest rung of society? Moreover, despite the portrayal’s tone, Jason Holliday is virtually unknown in pop culture. Why? He may be the hottest mess in town but he’s also the first documented “snap-queen.” 

With dreams, musical numbers and graphic emotions, Jason and Shirley revisits that fateful meeting and explores this true story in a new light. 

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