One night about seven years ago, Robert Yapkowitz and Richard Peete, two guys with budding careers in film, found themselves hovering over the jukebox at a Brooklyn bar. They were pleasantly surprised to find songs by two revered, long-departed folk artists, Fred Neil and Tim Hardin. Tantalized, they flipped through the offerings in search of songs by another cult artist they loved: the beguiling and eternally enigmatic Karen Dalton. They found none.

“We said right there that we’d make a movie about Karen Dalton and shoot and release it by the end of the year,” Yapkowitz recalls. And so, over the clank of beer bottles, a passion project was born. It ended up taking Yapkowitz and Peete much more than 12 months, but their documentary, Karen Dalton: In My Own Time, arrives in theaters October 1 before streaming in November. (Wim Wenders is the executive producer.)

Bob Dylan, Dalton, and Fred Neil perform at Cafe Wha?, on MacDougal Street in New York, 1961.

“Karen had a voice like Billie Holiday and played guitar like Jimmy Reed,” Bob Dylan, an avowed Dalton fan, once said. The Holiday comparisons grated on Dalton’s nerves, but there’s something to them. The singer, who died in 1993 at the age of 55, had a voice that was plaintive and doll-like, earthy yet otherworldly. It was also eerie and vaguely antique, like something off an old 78-r.p.m. record—the sound of a ghost emanating from the parlor. She and Dylan shared stages together in the Greenwich Village glory days of the early 1960s, when Dalton—a half-Cherokee Okie with a luminous presence, like Ali MacGraw with a Gibson 12-string and a banjo—hit the scene like a meteor.

It’s easy to go down the seductive rabbit hole of Karen Dalton—beautiful creature, elemental talent, troubled soul. (See also: Syd Barrett, Roky Erickson, Sandy Denny, Judee Sill, et al.) She’s a cult hero’s cult hero, one who was adept at cultivating mystery and performing disappearing acts; as early as 1966, Fred Neil reportedly told an interviewer, “No one knows where she is.” Dalton tended to flit from place to place—out to Colorado, back to New York, up to Woodstock. It turns out that before Dalton even arrived in the Village, she’d had two children and two marriages by the age of 21. She was emotionally well traveled; her life was a swerving journey though secrets and past lives.

She and Dylan shared stages together in the Greenwich Village glory days of the early 1960s.

In My Own Time is the first ambitious attempt to find Dalton: who she was, what she did, where she sits in the pantheon. Yet the filmmakers wisely approach their skittish subject with a gossamer touch: They refuse to entirely pin this fascinating butterfly down. To do so would be antithetical to the very concept of Karen Dalton; it might also be impossible. “There are parts of Karen’s life that we’ll never know,” Yapkowitz says, “and we were researching it for seven years.”

He and Peete interviewed high-placed fans (including Nick Cave and Rick Moody), friends and collaborators (Peter Stampfel, Lacy J. Dalton, Michael Lang), and family (notably the singer’s daughter, Abralyn Baird). Cave says of his first encounter with “Something on Your Mind,” Dalton’s best-known track, that the music wasn’t just jarringly sad—“It was perfect.” Stampfel points out that among the 1960s folk scene it was Dalton who was authentically folk. Her daughter backs this up, providing hitherto unknown details about Dalton’s Great Plains girlhood; photos show a radiantly cute child whose life could have been documented by Dorothea Lange or Walker Evans.

Like Ali MacGraw with a Gibson 12-string and a banjo: the poster for the new documentary.

Artfully weaving rare archival footage with Super 8–textured B-roll, Yapkowitz and Peete bring us way inside Dalton’s mysterious and often bleak universe, an effect heightened by passages from the singer’s own poetry and journal entries. These are voiced with startling intimacy by the singer-songwriter Angel Olsen. (As we hear Dalton’s words and watch them scroll by on the screen, the question arises: Why didn’t Dalton, a cover artist extraordinaire, set these bracing observations to her own original music?) This huge cache of Daltoniana—comprising nearly 500 pages, by the filmmakers’ estimate—was destroyed in a 2018 fire. It survives because Yapkowitz and Peete had the foresight to scan it.

In My Own Time takes its title from Dalton’s second album, recorded upstate at Bearsville Studios and released in 1971. (It would also be her last.) Along with the Band’s Music from Big Pink and Van Morrison’s Moondance, it’s a quintessential Woodstock album, from the era when that Catskills village was a Brigadoon of music titans, from Dylan to Todd Rundgren, the Laurel Canyon of the East. But Dalton was not destined to be a titan. In fact, she seemed to find the notion of stardom downright distasteful, despite an unending series of near misses, from her friendship with Dylan to touring with Santana. “I was actually surprised at how close she got to stardom,” Peete says. “A lot closer than I had imagined.”

Dalton was a magnetic performer, who, either through hardheadedness, insecurity, or an ironclad belief in the music’s noncommercial authenticity, was as hostile to the grasping American marketplace as Thoreau was. Like him, she seemed to prefer a hermit’s life. But her own version of isolation—in trailers and hovels—wasn’t exactly transcendental. She spent the long dénouement of her life in poverty and obscurity, self-medicating with needles. By the time Dalton died, of AIDS in 1993, she was a virtual unknown. In the 21st century, reissues of her slim two-album catalogue finally brought her an audience, small but adoring.

The incompleteness of Karen Dalton—the spare output, the few film clips, the early death that closed off the possibility of a second act—has nurtured the legend. “It’s a dark world,” Cave says of the world of Karen Dalton. It is. But, as In My Own Time makes clear, there is more to that world: talent, heart, and guts, not to mention shimmering, one-of-a-kind music. “She’s usually portrayed as a one-dimensional figure—she was tragic,” Yapkowitz says. “But we didn’t want to see Karen Dalton as a victim. We wanted to celebrate her bravery.”

Mark Rozzo is an Editor at Large for Air Mail

Karen Dalton: In My Own Time is in theaters October 1 and on digital platforms November 16