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Jon Voight in a closeup recalls shooting a scene for 1969’s Midnight Cowboy, where his character had to run half-naked down a dusty street. Afterward, something about the gritty tale of naive sex worker Joe Buck and his ailing con man friend overwhelmed director John Schlesinger.

“What have we done?” he told Voight. “What’ll they say?”

“We will live the rest of our artistic lives in the shadow of this great masterpiece,” Voight told him, thinking fast. It was “the most ridiculous thing I could think of” for reassurance, he notes.

“But it turned out to be true.”

That anecdote falls at the beginning of the documentary Desperate Souls, Dark City and the Legend of Midnight Cowboy. Inspired by Glenn Frankel’s 2021 book Shooting Midnight Cowboy: Art, Sex, Loneliness, Liberation, and the Making of a Dark Classic, the film doesn’t show how prescient Voight turned out to be, relying on viewers to have some knowledge of the landmark Oscar-winning film.

Rather, it’s an immersive kaleidoscope of reflections from the people who helped Midnight Cowboy come to be.

Director Nancy Buirski (A Crime on the Bayou) blends insightful interviews and archive footage to craft a picture of the era when Midnight Cowboy debuted, touching on the Vietnam War, New York City’s financial troubles, and attitudes toward homosexuality. Shots from Midnight Cowboy fade in to real-life New Yorkers, anti-war footage, or scenes from Schlesinger’s documentaries, enhancing the film’s feel as a product of those times.

While homosexuality is a subtext in the film and the book Midnight Cowboy by James Leo Herlihy, Schlesinger made the relationship between Voight’s Joe Buck and Dustin Hoffman’s Ratzo Rizzo more of an unlikely friendship based on compassion.

Herlihy wanted to write a book about how cruel people could be, someone notes, but Schlesinger, whose family accepted his homosexuality as long as it wasn’t “conspicuous,” believed were alternate relationships to family. Never comfortable in his own skin, he was drawn to this tale of outsiders.

“This story was about loneliness,” Voight agrees.

Made for $3.6 million, Midnight Cowboy grossed $44.8 million and won three Oscars: Best Picture, Best Director, and Best Adapted Screenplay. It remains the only X-rated film to win the Academy Award for Best Picture, although it’s since been rated R with no changes to the original content.

Desperate Souls is partly a bio of Schlesinger and screenwriter Waldo Salt, who had been blacklisted for refusing to testify before the House Committee on Un-American Activities in 1951. Schlesinger came from a school of documentary filmmakers and was interested in realism, much like many early postwar films in Europe but unlike Hollywood at the time.

His detached view of the culture of New York’s Forty-Second Street, then full of peep shows and other X-rated venues, was part of his attraction to it, says Waldo Salt’s daughter, Jennifer Salt.

Thanks to progressive Mayor John Lindsay, the production filmed on the streets of the Big Apple, leading cast member Bob Balaban to remark that this was the first film he’d seen where New York City actually looked real, “not like Judy Garland was gonna come along singing ‘Easter Parade.’”

Interviews with Voight and Hoffman reveal how both chased Schlesinger to be cast for their roles. Hoffman, amusingly, was fresh off making The Graduate and friends with a group of artists who thought there was “a dignity in being unemployed.”

Director Brian De Palma briefly pops in to note that the film’s cultural acceptance ties into 1969’s Easy Rider, which connected with audiences in a way that big-budget musicals at the time did not.

Midnight Cowboy was “resolutely unglamorous” but expressed the zeitgeist, someone notes, largely because it didn’t target the obvious 1960s themes and problems.

Desperate Souls is a haunting look at two lost souls on screen in a tumultuous time and the people behind the scenes who cared enough to bring them to life.

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Valerie Kalfrin

Valerie Kalfrin is an award-winning crime journalist turned freelance film writer whose work appears at, In Their Own League, Script, The Hollywood Reporter, and other outlets. Also a screenwriter and script consultant, she’s passionate about challenging stereotypes about gender and disability. Let’s tell better stories and tell stories better.