20 Years Of Supa Dupa Fly: We Talk To Missy Elliott About Her Landmark Debut

In a sea of offers for fast money and fame, then-Elektra Records execs Sylvia Rhone and Merlin Bobb approached her with what she desired, holding a single circumstance to the deal: Elektra would distribute Missy’s The Goldmind imprint if they got a Missy Elliott solo album out of the deal. Working at a three-records-a-day pace - with this dealbreaker as the only thing between Missy and her dream - Supa Dupa Fly, the seminal 1997 album that forecasted several decades into its genre, was created in two weeks: the first for Timbaland to track Missy’s vocals, the second to gather the features.

Recorded at Master Sounds Studios in Virginia Beach - just a half-hour away from Missy’s native Portsmouth - the core creatives locked in from around four in the afternoon to three in the morning. The daily core: Timbaland, Larry Live, and Magoo. No one else was invited in, to prevent any external disruption of the workflow by having too many minds and opinions on the work. The only other sanctioned activities: food and smoke breaks, the latter Timbo didn’t partake in. “That was my heyday, so I used to smoke trees! I most definitely had the trees on deck!” Missy recalls with a fond laughter of the memories.

When she wasn’t sneak-listening to Rick James or slapping Prince and New Edition 45s on the player as a child- “I’m talmbout with the big needle: where it get dust on it and you just gotta keep wiping the needle off” - Missy indulged in her secular background of the Winans, the Hawkins, and the Clarke sisters. She cites Salt-N-Pepa as the reason she raps, alongside Queen Latifah and MC Lyte as the elders of her style. In school, Missy was the genius class clown: she mismatched her clothes on the regular, beating on the locker, freestyling slang and sound effects to match it since she didn’t have the studio, much like the homies did at your lunch table before screens became everything. This, plus the trees, gave the foundation for her lineage of phonetic trills she remixed throughout her career, tucking a seemingly-nonsensical surface into any and every pocket at will, giving life to the flavors you can’t find words for. And in the studio, every song was built just like that: from a random assortment of sounds and loops, working a few at a time until Missy and Timbo settled on a foundation hot enough to continue with.

“The genius thing about it was--which, I wish we had those reels, cuz you know, back then it wasn’t Pro Tools, it was reels-- the loops of those songs that was on the Supa Dupa Fly album, Timb would maybe find three sounds and I’d just rap or sing something over those three sounds and once I laid my vocals, then he would build everything around that,” Missy says.

Original painting by Jay Katelansky.

The two-week retreat permeated the mainstream with a bang, it's 129,000 first-week sales netting a #3 start on the Billboard 200 and a #1 on the R&B chart, the highest-ever debut by a female rapper at that time. Critically, Missy was taking her first step to becoming the superstar she fantasized of becoming back when she used to practice in front of her dolls, arranged in her room like a ravenous audience who screamed for her. In an ironic twist of fate, Missy experienced Supa Dupa Fly’s impact while still living with her mother in Portsmouth: being stopped in the store, fans throwing up 2 up, 2 down (a VA hand-sign) the rare times she hit the club, and keeping a selection of her career’s most coveted outfits in her room, until revisiting about a year ago to gather her things before her mother sold the home.

“She was like “Go through your stuff because it’s probably some stuff that you’d wanna keep,” Missy says. “And I went there and I started seeing mad clothes from that time, and I’m like ‘I was still living here?’ I was standing there looking at my clothes like: ‘I was still here doin’ ‘Sock it 2 Me?’ Like these are “Sock It 2 Me” outfits, “The Rain,” it was crazy!”

20 years later and Supa Dupa Fly remains a sonic ode to its predecessors and a rare blueprint for the new millennium: it’s boom-bap, electronic slow jams, bombastic horns and chopped-up guitar licks arranged into a collage of today and tomorrow’s Black music. It remains perched atop the Golden Era mythology - dropping around the same two-year frame as many seminal works from Pac and B.I.G., the Fugees, Lil' Kim, Wu-Tang Clan, and A Tribe Called Quest to name a near few - but a listen now wouldn't casually place it there.

Supa Dupa Fly manages to preserve the soul while pushing the future; such a focus requires sealing oneself from the world, unconcerned with the triumphs and turmoils of a popular dialogue. With the right calibrations, this quarantine forced Missy and Timbo into an uncompromising space with nothing to turn to but the voices and melodies in their heads. The result: a rap album that paid respect, but abandoned its surroundings for something greater. Now the SoundCloud crate diggers of tomorrow use these songs to frame their progressive spirits, and Missy's effortless rap/singing is a default for post-Drake modern rap radio where the slightest amount of melody is a default for even the hardest gangsters.

“I didn’t ever look at it as being risky,” Missy said. “I looked at it as being the best of both worlds because if you wasn’t a person who was into hip-hop or rap like that, you got a chance to enjoy the singing part. If you was straight hip-hop, then you got a chance to enjoy the rap part of it. I thought it was always great to blend the both because I love both equally. Just because I loved both, I tried to intertwine them all the time.”

The Supa Dupa Fly visuals follow Missy’s innovative mold to a tee: colorful, vivid Afrofuturist projections of the world she built in the music. “The Rain” was her first portrait of that brave new world: a Hype Williams-directed breakout effort with green hills, a beach, Black luxury, and a fisheye lens of the hottest talents in the industry of the time. Thanks to Laurieann Gibson, “The Rain’s” choreography was built intuitively around Missy’s natural body movements, giving it the quirkiness for the world to emulate. In this world, Missy was the beautiful superstar that never appeared the way she should in the world she inhabited: a thick, fly Black woman with endless outfits who can rock the curls and the braids, who’ll outdance you, outrap you, outsing you, and break up with you before you dump her. And, contrary to popular belief, the legendary inflatable trash bag… was a patent leather blow-up suit, which Missy corrects through a giggle on behalf of stylist June Ambrose for the umpteenth time. “Noooooo, it was patent leather, [June] gags every time, she cringes when she hear that!”

Missy lauds Hype Williams’s fearlessness as a driving force to help manifest her visual aesthetic when most other directors would stifle themselves in the conventions of their oeuvres with other artists. Every idea he had that he didn’t or wouldn’t try on anyone else, he took to Missy; two auteurs sharing an uncanny ambition that set their work as the standards. “The way he described my music to me, I knew that he got it,” Missy says. “He’s like ‘Yo, this is some futuristic shit, so… we gon’ have to take it there.’ And I’m like ‘Well, let’s go.’”

Her music videos became an event. Whenever “The Rain” or “Sock It 2 Me” dropped, it was to TRL or 106 & Park with the whole world waiting to be transported into her universe at any given time. Like the memory of her dancing on a kitchen chair to Janet Jackson’s “Pleasure Principle,” or searching for the moves to a VHS of Janet’s “Control,” she became the human highlight reel for women and girls to love, be loved, and do the damn thing no matter how the world commanded them to look.

For every question I have about Supa Dupa Fly’s intentionality - the majority of the album’s features being women, the broad scope of depictions of love for oneself and others, her impact as a feminist icon - she insists none of it was deliberate, that she only considers these talking points when writers like me bring them up, and apologizes for not giving me the “juice juice” on everything.

“I just was workin’, man,” she said. “Just doing what I love. It wasn’t calculated, I didn’t have an agenda or anything. And I didn’t think ‘Listen… years from now, they’re gonna say this, they’re gonna say that…’ I wasn’t even thinking years from now. All I was thinking is musically, sonically… I felt that we were never in the year of the ‘90s or 2000, that we was always in 3-G.”

I ask her about “Best Friend” and how her chemistry with Aaliyah was so palpable on that record, and what it meant to her now. She said she wanted someone to hear it and feel like they were listening in on their homegirls talking to each other, regardless of how famous the two were:

“That song is always gonna mean so much to me. I wouldn’t have did that record with anyone else but Aaliyah,” Missy says. “When I wrote that record, I was thinking like… ‘This is what friends do.’ Be on the phone, and it’s always that one friend that’s telling her other friend ‘I’m done, I’m done with this cat! Woo woo woo…’ And you just got that friend like ‘Yo, I’ma be here in your time of need. Forreal forreal, he ain’t no good, but… I got you. I’m slidin’ witchu.’ And because of me and Aaliyah’s friendship, I felt like that was the perfect person to have that song with and it feel natural as if me and her was on the phone, and she telling me or I’m telling her about somebody.”

Painting by Jay Katelansky

I tread the inevitable mention of today’s political climate. Missy doesn’t watch the news because it depresses her and drains her energy when she thinks of where we’re headed; ergo, the isolation for her creative process. She mentions her This is Not a Test! album - which dropped a year after 9/11 - as a precursor to today’s heightened social involvement post-Black Lives Matter, pointing to her aesthetic then (“the whole Black Girl Magic look, afros, all that stuff”) as her feeling the climate shift even then. She thanks the grace of God for her financial security so she can sit on music and drop whatever she wants without having to match today’s rampant digital output just to keep her name (“If I put it out, and even if everybody don’t like it, at least I felt like it was fire if I put it out.”)

As listeners of the now - easily engulfed by the consequences of the modern music industry’s unpredictable, algorithmic euphoria - it’s difficult not to subject new artists and their works to a furious scrutiny. We’re ever eager to dissect their trajectories for the fact and fiction; the organic and manufactured means of who becomes popular to whom in which period for which reasons. Therefore, when a timeless artist like Missy - now 45, still holding the power to shake the game at a moment’s notice - reduces a piece of timeless work as the means to an end, one’s first instinct is to deny such an assertion as mere hearsay.

Supa Dupa Fly was really a moment in a bottle: it was two childhood friends doing what they always did to get what they wanted. Missy’s still living and creating by her motto: “Work like you never had a deal,” the tireless approach that allowed Supa Dupa Fly, the first piece in a timeless legacy, to come to fruition.

“I encourage women, men, everybody to be themselves and not compromise,” Missy said. “Cuz you’d rather be able to sleep at night knowing something didn’t work, but you loved it… than to not be able to sleep at night, doing something that’s not you. And kicking yourself in the ass over and over again like ‘I knew I shouldn’t have did that,’ whatever it is. I stand by that.”