“Why is the measure of love loss?” Jeanette Winterson asks in her 1992 novel Written on the Body, where a genderless narrator mourns their previous relationship so deeply they write long, vivid paragraphs cataloging the departed lover’s body parts, her legs, torso, mouth, hair, trying to reconstitute the whole through the memory of fine details. Take stock of what the world looks like after a relationship ends; it’s an emptier one, as if an apocalyptic event removed half of everything from existence. Furniture is gone. Certain perfumes and cooking smells no longer hang in the air. Friends who were their friends are no longer your friends. It can feel disorienting to move through this new world where someone who was always there is now missing, like tiptoeing the edge of a crater.

Plenty of breakup albums past and present attempt to depict this feeling, whether from a place of hurt or acceptance or stranded at an uncertain point between. But Meshell Ndegeocello’s masterpiece, 1999’s Bitter, lives inside of it. The doomed timeline that your life diverted into when you broke up with the person you loved the most. The silence that took over every room of the apartment, the darkness that filled in that silence at night. Bitter’s songs develop in this dark space like spider webs in corners. Piano chords and acoustic guitars tremble at the threshold of being heard, while Ndegeocello’s voice cradles a sentiment so extraordinarily vulnerable that it couldn’t be delivered in any register louder than the softest breath, lest it fall apart entirely: “You made a fool of me/Tell me why.”

Ndegeocello made Bitter from a place of abandonment, though it was more creative than romantic: When 1996’s Peace Beyond Passion was misunderstood by her record label, radio, and music television, she threatened that it would be “the last Meshell Ndegeocello album,” that she would retreat into making instrumental music instead. One of the singles from Peace, “Leviticus: Faggot,” about a gay teenager who is beaten to death after getting kicked out of his home by his parents, had its video banned from BET, and Peace itself, an album that swings through various forms of queerness and spirituality in an attempt to find an evasive truth, was worlds more complex than Ndegeocello’s debut single and only solo mainstream hit to date, “If That’s Your Boyfriend (He Wasn’t Last Night).” (Note that from her very first single she was interested in people slipping in and out of categories like liquid.) “I’ve already said as much as I can say in my songs at this point,” she said at the end of Peace’s promotional cycle. “I need a break… I hurt.”

Bitter blossomed gradually out of this hurt. If she was going to make a new album, she needed a new approach. She wrote a few songs with David Gamson, former member of Scritti Politti and producer of Ndegeocello’s first two records. While those albums were smooth soul-funk records chopped up by drum machines, the material Ndegeocello was writing merited a recording process that was more subtle, more live. The songs seemed to fall in line with other singer-songwriters of color that had traveled across the racial boundaries of genre before her, into a kind of celestial folk music: Joan Armatrading, Richie Havens. (Blackness isn’t genre, Ndegeocello is more or less always saying with her work—a person’s race doesn’t necessarily predict the sounds they’re surrounded with or eventually make.) She hired producer Craig Street, who had just recorded a standards album with k.d. lang, to foster this sense of naturalism, to make songs that were less composed and more played, a room of musicians responding to each other’s faintest gestures.

How better to craft a work of art about loss than with an act of subtraction? Peace Beyond Passion’s songs constantly move, developing new branches of melody as they go. Bitter, by contrast, would almost seem static if you didn’t also register its constant quiverings. They are spectral songs in terms of genre, spartan as folk, dynamic as jazz, on edge with feeling as the most incandescent soul record. Sometimes the music stirs lightly, as if it’s been awake in bed for hours, depressed, only moving when necessary. Sometimes it follows a memory back to when the relationship was strong, then casts its focus to when it was only a few strands away from fraying; this is the feeling the title track spins through, just Ndegeocello’s voice and an acoustic guitar wringing the final poisoned kisses out of a courtship that’s run its course. The whole album is like this, an account of a relationship that is constantly adding footnotes to itself: This is where I was almost unfaithful to you, yet here as well is where I felt hopelessly devoted to you. Monogamy is untenable and eventually unbearable—as Ndegeocello sings, “No one is faithful/I am weak, I’ll go astray”—but someone can still be the only person who satisfies you, their love your lone “saving grace.”

It’s at the center of these tensions where Ndegeocello can most effectively play the masculine and feminine against each other, inhaling as one, exhaling as the other, wearing each persona like a mask. A man loves his girlfriend with “sweetness and sincerity,” while she only offers him the pretense of love, a deliberate reversal of how heterosexual relationships are usually depicted. Later, in “Loyalty,” Ndegeocello creates and fully inhabits a man and a woman who, despite the broken homes they emerge from, are trying to find something permanent in each other, even though something yawns beyond them, a future they can’t quite see clearly, where everything they know may end in hurt—as the girl’s mother (another perspective Ndegeocello manages to sneak into) tells her, “Trust only in change, ’cause hearts change/But betrayal always feels the same.”

Like her hero Prince, Ndegeocello’s work is constantly flowing between different embodiments of gender; if she seems relaxed wherever she temporarily touches down on the gradient it’s because she could be one or the other or really anything at all at any given time. “[Prince] fights his femininity and he fights his masculinity,” Prince’s guitarist Wendy Melvoin, who plays on both Peace Beyond Passion and Bitter, said. “Meshell doesn’t pay too much attention to being male or female. She’s not self-conscious about it, and that’s in her music. Sometimes she’s a boy, and sometimes she’s a girl.” Inasmuch as her albums invoke the concept of gender, it doesn’t remotely feel like a binary, like a switch being flipped. Ndegeocello is masculine here, feminine there, without ever losing her coherence as a person. And Bitter is full of different types of voices and relationships as she is—masculine, feminine, lesbian, straight, all like different imprints in the sand made by the same wave.

As on most of her records, Ndegeocello incorporates a cover in the Bitter tracklist, like a conversation with the past to determine where her own music is. Here she covers Jimi Hendrix’s “May This Be Love.” Her version of the song—which in its original form is a dreamy electric crackling, a love song hummed by power lines—is so smooth it’s like a pebble taken from the bottom of the ocean; where Hendrix’s recording gave off sparks, Nedegeocello’s goes liquid in your grasp, a feeling that nothing could contain. She replaces the bridge with an ambient whirlpool, and you hear Ndegeocello’s voice, surrounded by washes of sound, reciting Hendrix’s words instead of singing them, as strings curl outward from the slipstream of keys. It’s masculinity submerged, crystallized, held in the feminine, a perfect prismatic expression of Ndegeocello’s own sexuality through the vessel of someone else’s song; it’s also the centerpiece of Bitter, an album about being held, or at least about wishing you could still be held, by someone who complements you, who is you and isn’t you at the same time.

Critically, Bitter was beloved—Newsweek declared it album of the year for 1999—but it received little promotional muscle from Ndegeocello’s record company, Maverick (she had once again turned in an album that sounded little like “If That’s Your Boyfriend”), and was released to sales as motionlessly quiet as some of its songs. She heard the undertones looming beneath what her record company and the sales were saying: She’d seemingly abandoned the Black music that had gotten her on the radio. But the music on Bitter isn’t any less of a fusion than the records Ndegeocello put out before and after it. It may be her simplest, starkest record, feeling years older than it is, like wood floors creaking underfoot; but that doesn’t keep it from being a soul record, just a soul retreated inward, a door closed behind it—instead of witnessing its full force, you glimpse the evocative shadows of its movements.