"For of all sad words of tongue or pen, / the saddest are these: 'It might have been!' " is the poignant ending to John Greenleaf Whittier's 1856 poem "Maud Muller."
The words come to mind in viewing "Garland Jeffreys: The King of In Between," a documentary about the New York musician, who, while revered by a sizable cult following, never realized the mainstream success widely predicted by those in and around the music industry. A contemporary of Lou Reed and Bruce Springsteen — both of them fans — Mr. Jeffreys's commercial aspirations were burdened by an industry intent on categorizing artists and genres.
But Mr. Jeffreys, who is in the final stages of Alzheimer's disease, defies such labeling. Growing up in Brooklyn's Sheepshead Bay neighborhood, he was smitten with the doo-wop of Frankie Lymon, snuck into Manhattan jazz clubs as a teenager, and absorbed the diverse sounds of a Greenwich Village exploding with creativity as the beat poets gave way to a folk revival and rock-and-roll. Hearing reggae in the early 1970s, he was in the vanguard of American artists who would smoothly incorporate it into their own music.
"It was very clear that this was a person who, because of his uniqueness, because of the fact that he's so hard to classify, would have a lot of trouble," the music journalist David Hajdu says in "The King of In Between." "Where does this Black-Puerto Rican guy from Brooklyn fit in? What is he?" Rather than celebrating the multitudes embodied in one man, the tendency of the music industry, and of audiences, was toward confusion. "Categorization is the reality — and the tyranny — of the music industry," Mr. Hadju says. "And he's been a victim of it."
Nonetheless, the documentary, directed and co-produced by Mr. Jeffreys's wife, Claire Jeffreys, is celebratory, bringing deserving notoriety to its subject, who repeatedly explored that "in between-ness" in his music. The 70-minute film will be screened at LTV Studios in Wainscott on Saturday at 7:30 p.m.
"He definitely felt excluded from both sides, both communities," Ms. Jeffreys, a first-time director, said last week. "I think that desire to compartmentalize is almost like a biological imperative. We're all programmed to fear the other, and anyone that looks different, sounds different . . . if you really look at the world, you will see that that's the cause of all strife. We think we're better because we're whiter, or because we're richer, or because we're Christian, whatever." That impulse, she agreed, is "so limiting."
"Half Cult Figure, Half Recording Star," reads a newspaper headline depicted in the film. "I'm a legend you see / Black and white as can be / And I give you this ballad of me," Mr. Jeffreys sang on his first solo album in 1973.
In home movies, Mr. Jeffreys, his wife, and their daughter, Savannah, are depicted in East Hampton Town, vacationing at the beach. The family rented in Springs, Ms. Jeffreys said, and Mr. Jeffreys performed at the Stephen Talkhouse in Amagansett, the East Hampton Neighborhood House, and Bay Street Theater in Sag Harbor.
Laurie Anderson, another genre-defying artist, is also featured. Ms. Anderson has a house in Springs, and Reed, whom Mr. Jeffreys met when they were both students at Syracuse University, was her husband. "Lou really admired Garland, as well as loved him," Ms. Anderson says in the film. Reed, who died in 2013, "had a great big soft spot for that kind of singing."
"Garland and Lou were really close," said Ms. Jeffreys, who confessed that "I had no idea what I was getting into and how arduous and lengthy and expensive it was going to be" when embarking on the documentary. "It was almost like a graph where as I got further into it his illness progressed. Now he's completely unable to grasp anything going on and doesn't know, and it's really sad because he'd be thrilled to hear what people are saying and to experience a screening. He would be beyond excited. That's been bittersweet. I was thinking, 'Let me tell the story, see what happens,' and here we are."
The couple met in 1981. Throughout the experience of making the documentary, Ms. Jeffreys said, "I felt I was deepening my understanding of someone I knew so well," learning of "all this life he had lived before me."
A question-and-answer session with Ms. Jeffreys and Peter Parcher, an entertainment attorney who lives in Amagansett, will follow the screening.
Tickets for "Garland Jeffreys: The King of In Between" are $15 in advance and $20 at the door. Reserved V.I.P. table seats are available for $35 and include a drink ticket. Tickets are available at ltveh.org.
"He's in the great singer-songwriter tradition of [Bob] Dylan and Neil Young," Mr. Springsteen says in the film. "One of the American greats."
