In the summer of 1997, following the murders of both 2Pac and the Notorious B.I.G., hip-hop underwent a transformation. Amid the continued rise of Clinton-era “tough on crime” policies, the unexpected and widespread popularity of gangsta rap from the projects to the suburbs showed no signs of stopping. But the music industry itself felt bogged down by the real-life violence that rap stars spoke of. As a rising star, Missy Elliott was frequently hired by Bad Boy Records to write for some of its hottest stars, and she even ran into Biggie Smalls the night he was killed. But rather than dwell on the tragic murder and roiling violence of rap at the time, Missy sought to capture the feeling of a generation breaking out of societal norms in the name of amusement and pleasure with her debut album, Supa Dupa Fly.

When faced with times of escalation, the Black community often folds within itself to find solutions. With hip-hop, the Black youth that had fought and raged to be heard saw themselves at the helm of what would become a billion-dollar industry. By the late ’90s, rap had shifted from gritty biography to decadent stories about children of the crack era growing up to be millionaires off their own talents and oral history. Those who had been marginalized were now the Black nouveau riche—a movement led in the East by Bad Boy Records. The label’s music focused on a new class of black millionaires who wanted to talk more about what they were looking forward to rather than leaving behind, and Missy was right there in the mix.

Though Missy was mostly writing for R&B stars and was then known as a singer, it seemed inevitable that she would try her hand at rapping. The late ’80s and early ’90s had introduced New Jack Swing: a fusion of hip-hop rhythms, samples, and production techniques with urban contemporary R&B. The success of Teddy Riley, a Virginia native and father of New Jack Swing ushered in the reign of the Neptunes and Timbaland: producer powerhouses who would eventually become titans of the industry by running with new styles of production. By virtue of its geography, Virginia connected the tenacious sounds of the Northeast and the looser style of the South. It was this very storm that brewed up the magic of Missy and her partner in beats, Timbaland.

High school friends who had met in their home state of Virginia, Missy and Timbaland spent the better part of the ’90s writing for almost every major R&B act at the top of the charts, including SWV, Jodeci, and Aaliyah. By the July 15, 1997 release of Supa Dupa Fly Missy was already the head of her own imprint, The GoldMind Inc, which co-released the project. Considering the male dominated landscape of the era, this feat was not only incredibly impressive for a female rapper but an undeniable catalyst for the way the genre would take shape in the new millennium.

Hailing from Portsmouth, Virginia, Melissa Elliott had spent her entire life onstage, even performing for her own dolls at a young age. Getting her start singing in church, she became a regular fixture in talent shows across the city and state. She first linked up with Timbaland while working on material for her all-female quartet, Sista. The group got a break when they caught Jodeci’s DeVanté Swing backstage at a show; he took the group on. Unfortunately, the Sista project was shelved and Swing’s label, Swing Mob, later shuttered, but Missy took it as a lesson to become well-versed in songwriting and production. Timbaland has said that working with Missy was what first introduced him to the idea of melodies and made him think of his beats in song form.

While much of the music of the time was powered by well-known samples, including Bad Boy’s hits such as “Mo Money Mo Problems” (which flipped Diana Ross’ “I’m Coming Out”) and “Can’t Nobody Hold Me Down” (based on Grandmaster Flash’s “The Message”), Timbaland and Missy preferred not to sample—and if they did, it had to be interesting. Timbaland would speed up vocal samples just to use as them as a bass line. He used breakbeats in a unique way, too, employing them to create pauses and longer stretches of silence. The dead space became its own canvas within the beat where Timbaland could use overlays of beatboxing, clicks, and just about any cool sound, from a baby’s cry to an Egyptian flute. But it was the intuitive songwriting style and unique imprint of Missy’s pen that would make the duo a top-tier act.

By summer 1997, Missy had just finished writing nine tracks for Aaliyah’s One in a Million and made her debut as a rapper with a feature on Gina Thompson’s “The Things You Do.” Supa Dupa Fly was not a project she had long considered making but rather a reaction to the demand for her talent; the record was recorded within two weeks. “I did this album for my fans and not to make money, because I’m already making money with my songs,” she told interviewers around its release. Timbaland produced the entire project, and, together, they delivered a perfectly edited joint résumé.

It is impossible to separate the two throughout any of the 17 tracks. The record even has moments where they sample themselves, bringing back beats they had previously used for other artists: The syrupy guitar loop of SWV’s “Can We”—a song that notably starts with Missy’s soft whispers of being “supa dupa fly”—is interpolated on three separate tracks. It becomes a signature of sorts on an audio collage of Afrofuturism and Black Cool within the pop space.

Throughout the album, Missy follows the algorithm of pop lyrics: short and catchy phrases that boil down raw feelings in real time. However, her concerns were never with the sunny side of love but rather the work and pain that it takes for one to find real affection in this world. Tracks like “Beep Me 911” and “Sock It 2 Me” speak of a need for sex more than true love. “I was looking for affection/So I decided to go/Swing that dick in my direction/I’ll be out of control,” she sings. Missy’s brand of nasty singing was less Anita Baker and more in line with the hypersexualized bars of the likes of Lil’ Kim (who would become one of her best friends) and Foxy Brown.

This talk was especially innovative coming from a curvy, gender-bending woman who often appeared in exaggerated and animated form in her videos. In the iconic visual for “The Rain(Supa Dupa Fly),” Missy appears as a Michelin woman, dancing into the camera while wearing a giant plastic bag suit and biker’s helmet. The costume made her look even bigger than she was but also took away the obviousness that she was not a thin Lolita type. In the same video she wears a straight wig and sits on a hill twirling it in caricature of Lil Bo Peep. “We wanted to make fun of the ways record companies try to make black women look white,” Missy has said. “Fake hair, fake music.”

She was quite aware of how she looked and how the mostly male-audience of rap would receive her but she did not cower away from being the sexual aggressor. Missy rapped and sang about the woman who was self-assured and still sensitive to heartbreak; one that knew what she wanted enough to demand it but was prone to getting hurt. Even better, because of her “lack” of sexual appeal to the market of the time, she was able to skip the highly-sexualized performative nature of her female rap contemporaries. Many of those acts spun objectification into sexual empowerment, and Missy also empowered those who may have been told that their bodies were not attractive and therefore not valuable to consumers. What sells is not real life, and she made it clear that women like her have sex too. She also did not look down on her peers. Her focus was innovation, not morality.

One of the LP’s strongest ballads, “Best Friends,” featuring Aaliyah, tells the story of a woman who wants to protect her pathetic man in spite of what her friends may say. “My best friend say she sick of me cryin’ on the phone/Tellin’ how the men be doggin’ me/My best friend say don’t tell her nothin’ bout me and you/’Cause she ain’t showin’ me no sympathy,” Missy cries before belting out a chorus that declares her defiant commitment to be there for this wayward lover and whatever he may need. These everyday stories of love give her writing style the freedom to be as empathetic as it is explicit. Missy brings the biographical component of rap full circle for women here, not as just a raunchy counterpoint to its misogyny but an entirely new safe space for women to express their sexual liberation in dulcet tones.

Better yet, she was able to make her music contextually specific to its audience. Some of the album’s initial reviews criticized Missy’s writing skills, claiming that the lyrics were lacking in substance and structure. But whereas contemporary pop had been mostly for a white audience, R&B was a decidedly urban (read: Black) art form. 1997’s top love songs were far from sexually explorative: LeAnn Rimes’ “How Do I Live” and Backstreet Boys” “As Long as You Love Me” spoke of love as a virtuous happenstance, and heartbreak as a calamity that would stop all motor function. Missy spoke of tortured love at the hands of men that were not quite respectful and most definitely bad for you-- the kind of relationships you needed friends to survive through—and she spoke of it in the language of the hoods she came from. What some wrote off as “lazy” and “uninspired” lyrics were simply in AAVE, speaking directly to the audience from which they came. On “Beep Me 911,” Missy takes on the role of a spurned lover who has had enough of being humiliated but may still hear him out. “Why you played on me, wasn’t I good enough for you/All those other girls you’ve been with can’t do like I do/Gave you all my dough when you needed it all the time/And if you planning on leaving me again then give me a sign.” These were not linear characters with strict moral standards on how they could be treated but real people with flaws who went against what was best in the name of comfort or even orgasm. These were topics that everyone could empathize with, marketed directly to those who informed the context.

Supa Dupa Fly speaks to the way Missy stuck to having fun with the music. She and Timbaland saw a opening to transpose the outlook of this young Black culture class and the very sound it used to define itself. What followed Supa Dupa Fly was many years of the industry attempting to reproduce what Missy and Timbo had created organically and by the time “Get Your Freak On” became an international success in 2001, much of the urban and pop landscape was employing Timbaland’s sound. But no one would ride his beats like Missy. On “They Don’t Wanna Fuck Wit Me,” the pair do back to back, almost freestyle verses, talking shit about their innate ability to crush tracks. Missy notes the things that seem to irritate her detractors, though they can’t stop listening. Over a sparse beat she rhymes, “I come back into my flow/My people just don’t know/They hate the way that I hee/They hate the way that I hee-haw/Cuz I got too much dough/You know my steelo/So what you come here fo’?” She brings back to focus the new money of rap’s Golden Age, which not only bought her a new lifestyle but the space and privilege to enjoy being herself.