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Y2K is fast approaching, the conveyor belt of manufactured pop is churning out diamond-certified bestsellers from tween stars of the Mickey Mouse Club. The rap counterculture is reaching new commodified heights. The deification of Tupac and The Notorious B.I.G. continues, casting shadows over the industry, but rap’s new children DMX and JAY-Z are garnering mass appeal recognition by way of the Internet Revolution. Women in hip-hop are emboldened, destroying the proverbial glass ceiling, yet one diminutive lady by the name of Missy ‘Misdemeanour’ Elliott, looms large.

In the summer of 1999, Elliott released Da Real World, rivaling the Hip-Hop Boys Club at a time when female MCs were still not seen as credible equals. This incited Missy to actively tackle the industry’s double standards head-on; fashioning a new paradigm of female-centric audacity within the realms of hip-hop and R&B. Coming off the back of her inter-dimensional debut Supa Dupa Fly, Missy Elliott faced crippling pressure to overcome the dreaded “sophomore slump”, and whilst Da Real World didn’t match its predecessor’s sales, the 17-track LP cemented Missy’s presence in the game as THAT bitch.

Aesthetically, Missy projected a surreal, TRON-like cyber-verse where there existed a level playing field between the sexes. She finessed a more affirmative feminist agenda as evidenced by the powerful cover art. Decked out in a power suit with a flip phone in her hand, and flash of lightning breaking the monochromatic skies, Missy was in a mood to disrupt the status quo and shake things up. In her own words, Missy proclaimed Da Real World a risqué “street record” for her “ghetto mothafuckers,” as professed in the opening line of the debauched, hedonistic “Hot Boyz.”

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Elliott consciously shifted the sonic terrain from the fun-loving, hook-laden anthemics of her debut to a quietly propulsive, more austere soundscape beamed in from the future. A marked strength was not to tamper with the chemistry she’d cultivated with trusted collaborator Timbaland, whose imprint poured mellifluously over every track. The Missy-Timbo partnership was never beholden to provincial sounds, their limitless synergy bred a kind of retro-futurism that sounded fresh and new. Timbaland’s trademarked, slowed down breakbeats and syncopated orchestrations provided the backbone through which Missy effortlessly spouted laconic affirmations. From the penetrating flows on “Beat Biters,” which referenced the imitators and Missy’s reputation as an instigator, to the heady rush of clangs on “We Did It,” to the climactic string arpeggios on “All N My Grill” – Missy’s capacity to shift her intonation in a rap-sung staccato over Timbaland’s ready-made beats meant she could channel both the lusty temptress and the big game, shit-talker with equal impact. Nobody was seeing her.

Da Real World was a showcase of Missy as a gatekeeper within the industry. She cherry-picked her own collaborators, catalyzing the careers of her fellow contemporaries, demonstrating in practice what sisterhood could achieve when a woman at the helm was co-opting talent. She featured both Aaliyah and Beyoncé on underrated deep cuts, before either made definitive strides in their respective careers. A month later, the latter would deliver (also owing to Missy’s dynamite curatorial touch!) The Writing’s on the Wall, with Destiny’s Child, which in turn codified R&B at turn of the new millennium. Missy also employed the talents of Jamaican dancehall star Lady Saw, for the paean to underground club culture on “Mr DJ.” Lady Saw was an originator of the ‘slackness’ performance style, criticized by conservative Jamaicans and West Indians for its crude sexuality and performative “vulgarity.” Missy, noting the derisive and outdated treatment of female performers like Saw, Lil Kim, and Eve, called on them to feature, thereby testing the delicate barometers of acceptability.

On the album centerpiece “She’s a Bitch,” Elliott re-appropriated “bitch” to epitomize a woman who knows her mind and who demands the best from those around her – a symbol of unabashed self-determination. ‘Bitch’ was and still is deployed by male MCs in hip-hop to insult, castigate and demean but Missy was having none of it, reclaiming the describer as a means to inspire a movement against pharisaic bullies within the industry. “She’s a bitch! When I do my thing/ Got the place on fire, burn it down to flame,” typified Missy’s repudiation of rappers as decorous wallflowers – wanting instead to normalize “confrontational” and “aggressive” as inverse positive describers of women in rap.

In the accompanying video, Missy presented the female form not as an ornament but one that wielded immense autonomous power. She’d already established herself as a visual auteur with the trippy, trash bag-adorned visual for her hit “The Rain (Supa Dupa Fly).” Yet for “She’s A Bitch,” Missy chose to be menacing and licentious by channelling the The Matrix, attired as a dominatrix Power Ranger emerging from water like an alien on the offensive. In an era of peak MTV and big-budget visuals, director Hype Williams tapped into Elliott’s wild and off-kilter imagination; fashioning a new type of “sexy” in the process.

Getty Images / Jeff Kravitz

“You may get females (that) want to look nice, they want to look glamorous in their videos, as opposed to me, I’m like, whatever,” Elliott told Reuters in 1999. “I want to have the video that when the TV is turned down, it’s not the song but the video that is so ill that you gotta turn the TV up.” Her aim was not to seduce but subvert the trope that women had to be submissive ‘video vixens’ – scantily-clad, draped on the arms of rap heavyweights as trophies. Unlike other rappers, Missy performed choreography, backed by a legion of dancers, enhancing the performative aspect of her brand and Missy’s ability to self-parody herself helped project the supremacy that came with embracing the eccentricities that exist within all of us.

In the last fear years, Missy Elliott is finally getting her dues – venerated alongside the greats in hip-hop. Just last week she was inducted as the first female rapper in the Songwriters Hall of Fame; the third rapper following JAY-Z and Jermaine Dupri’s inductions in 2017 and 2018, respectively. Earlier this year, she was presented with an honorary doctorate degree at the Berklee College of Music; revisionists finally basking in the afterglow of Missy’s 25 year legacy. In an age where hip-hop continues its path down obfuscation: breeding counterfeits, rewarding mediocrity, and infantilizing women artists and their contributions to music, it’s tantamount we revisit the distilled ingenuity of Elliott’s Da Real World-era as an exemplar of a boundless pursuit of genre-bending high art. Missy – for many girls (and guys) coming up in the game in 1999 – was the equivalent of Nas or Tupac. She faced her doubters with grit and verve, rivaled her competitors with gusto, advocated a sex-positive ethos, all the while following her own instincts.

Words by Shahzaib Hussain
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