Leslie Winer’s Music Was a Mystery in 1990. She Still Likes It That Way.

Leslie Winer seemed poised for stardom in 1990. The face of Valentino and Christian Dior the decade before — “the first androgynous model,” as Jean Paul Gaultier called her — had turned to music. Her first single, “Skin,” featured a club-ready backbeat and a hook about love and acceptance perfect for the United Colors of Benetton era. John Maybury, the director of Sinead O’Connor’s “Nothing Compares 2 U” video, made the track’s clip. But Winer’s chiseled visage didn’t appear in the abstract video, and “Skin” simply disappeared.

The mosaic of samples, hip-hop drums and slow Jamaican-styled bass lines that defined what would have been Winer’s album “Witch” (recorded under the hard-to-file name of ©) was shelved until 1993. By then, Madonna had adopted that sultry sound for “Justify My Love” and trip-hop had been defined by bigger groups like Massive Attack and Portishead. And Winer herself had moved on.

“I’m like a crazy lady at the edge of the village,” Winer said of her willingness to pioneer what became a new sound. “Never thought of any of it like that. Just the fun of making new tracks.”

Winer, 62, was chatting via video call for a rare interview from her home in France, sporting a black beanie visor pulled low under a blue hoodie, her brown hair now long and curling out at the neckline. A handful of old jazz albums and a copy of Willie Nelson’s “Always on My Mind” were visible on a shelf behind her. For the past 20 years, she’s lived about an hour outside of Paris on the way to Normandy, maintaining a monkish existence that suits her.

This month, the label Light in the Attic offered listeners a broad view of Winer’s musical legacy with the digital release of “When I Hit You — You’ll Feel It,” a decade-in-the-making compilation covering 1989 to 2018 that includes many tracks from “Witch” and the scattered songs she’s made in the years since. (It will arrive on vinyl in September.) The set includes ethereal electronics, booming breakbeats, dusty blues and a song with her daughter Mari, with Winer’s growled delivery holding it all together.

Winer’s life intersects with an array of icons and stars, yet to hear her tell it, musical stardom was never a goal. “It can be difficult to talk about making music with people because they conflate ‘making music’ with ‘popular success’ and image and brand and all these other frightening, soul-destroying late-stage-capitalist concerns,” she said. But the few people who heard her music at the time raved, including the BBC Radio 1 D.J. John Peel and Boy George.

Winer was born in Boston to a teenage mother of a prominent New England family and then was adopted. (She said she later learned the arrangement was an illegal transaction that took place in a hospital parking lot for a lump sum.) She was raised primarily by her adoptive grandmother, who instilled in Winer a love of words and poetry. Winer’s voracious reading habit continues to this day, though she now requires a magnifying glass to see the fine print.

By 17, Winer moved to New York City to study at the School of Visual Arts, though an encounter with the Beat legend William S. Burroughs soon altered that trajectory. He gave her books — “‘The Egyptian Book of the Dead,’ everything Denton Welch, Marguerite Duras,” she said — and encouraged her writing. But she also picked up one of his habits: heroin.

Winer’s S.V.A. studies were left unfinished as she took a different path, and began modeling. She worked with Helmut Newton, Irving Penn and Vivienne Westwood. She hung out downtown at the Roxy and uptown in the Bronx, taking in early hip-hop acts and bands like ESG. Her boyfriend was Jean-Michel Basquiat, though she’s quick to clarify: “Jean was not famous at this time. At all. He was just like everybody else. Making stuff.”

Modeling took her to London, where she soon fell in with a loose-knit group of musicians and artists. “What struck me about Leslie — once you get past appearance — was she’s one of the funniest people I know,” said the singer Helen Terry, a longtime friend. “She’s also one of the most polymathic. Leslie reads like other people breathe: constantly.”

Music was increasingly a part of Winer’s world. “Leslie was the first person I know who had an Akai 1000 sampler,” Terry added. “I went down with a pile of records and we ran them through it. The idea was to get some beats down and then see where they went.”

With collaborators including Terry, Karl Bonnie of the electro group Renegade Soundwave, the bassist Jah Wobble from Public Image Ltd., Kevin Mooney and Matthew Ashman of Adam and the Ants, Winer set about making her own tracks, drawing on the hip-hop she absorbed in New York and the dancehall she heard on All Saints Road in London, setting her own lancing, precise words atop it all. “The beat has to be right — or just the right amount of wrong — to be interesting,” Winer said. “Don’t have a problem with the words. Got a million of them.”

The new collection emphasizes how effectively Winer mashed up genres and approaches: the slow trip-hop of the era, breakbeats, the New Orleans’ funk band the Meters, samples of Gen. H. Norman Schwarzkopf and the words of the poet Charles Bernstein. “Tree” samples a jaunty Irish jig, chopped and layered so it buzzes like an Indian drone. Winer’s delivery — drawled yet quick, with a smoker’s rasp and acerbic tone — was nothing like the fast-talking slam poets of the era, instead hewing closer to the dry delivery of her mentor, Burroughs.

Winer often lifted passages from other writers, quoted other songs and applied her own dreamlike logic to it all, making something at once eloquent, blunt and cryptic. The monologue at the heart of “N 1 Ear,” for example, draws on a famous Gil Scott-Heron line and a women’s liberation broadsheet she found in London, ending on a powerful statement all her own: “I didn’t hit you, baby/When I hit you, you’ll feel it.”

Jah Wobble, who played on the songs destined for “Witch,” said it was clear the music wasn’t geared for the masses. “It was obviously more an art record than a commercial type release,” he said. “Once I finished the session, that was the last I heard about it. I assumed it was shelved.”

Winer kept making music in the years after “Witch,” working with the trumpeter Jon Hassell, the early sampler adopter Holger Hiller and another model turned musician, Grace Jones, before relocating to rural France and focusing on raising her five daughters. Over the years, a new generation slowly came to her music.

“It was at once familiar and completely new to me, a rarity to find,” the electronic producer Maxwell Sterling, who recently worked with Winer on a track for his latest album and an upcoming Tim Buckley cover, wrote in an email. “Each of her words hang in the air and react to rhythmic and harmonic information within the music, which never ceases to move me.”

Recently, Winer has collaborated with a new generation of producers, her low growl of a voice deepened and weathered with time. “I like doing vocals on other people’s tracks,” she said. “They’re like puzzles.”

Asked how to describe her writing style later via email, Winer wrote back: “I don’t see myself having to describe it.” She added, “It carries information that we don’t exactly have words for.”