You don't need to listen to Charli XCX to know that the year 1999 was more or less a battleground for pop-culture relevancy.

While much of the nation was going crazy over the hyper-futuristic film The Matrix, widespread Y2K hysteria, and the horrific mass shooting at Columbine High School that would lead to a national debate around violence lyrics in music, the growing musical counterculture—particularly around hip-hop and R&B—was catalyzing a bold changing of the guard.

Hip-hop continued to grow by way of the game-changing takeover of Cash Money Records, Eminem's meteoric rise and Dr. Dre's return, the East Coast renaissance while reeling from the tragic murder of the Notorious B.I.G., and arguably one of the most impactful class of women between the two black genres such as Mary J. Blige, Lil' Kim, Eve, Destiny’s Child, and, of course, Missy Elliott (among others). It was a perfect storm of women’s empowerment and rightfully reclaiming the narrative around black women, artists and fans alike, during the heights of several iconic hip-hop labels, including the house Missy and Timbaland built, Blackground Records.

After the Virginia native dropped her 1997 groundbreaking debut album, Supa Dupa Fly, Missy became more prolific as one of the most in-demand producer/artists between hip-hop and R&B while being tapped to work on songs from the Why Do Fools Fall In Love and Dr. Dolittle soundtracks, along with albums by Destiny’s Child, Ginuwine, Total, and Whitney Houston. And while eager fans were salivating for Missy’s long-awaited follow-up, Da Real World, few saw the pressure she endured due to fear of the dreaded "sophomore slump."

"It was my hardest album because by that time the expectations were a lot higher. Once you get over that sophomore album, you feel like you're staying. It was the toughest album to make," explained Missy in a 2014 Billboard interview. "I thought, 'What do people expect of me next?' There weren't any expectations for the first album. The second album was like, 'This first album has got all these great reviews so where I do go from here?' I was overthinking everything. I didn't think twice about videos, but yes for music. 'Ah, I don't like that.' I drove Tim crazy.'"

Missy "Misdemeanor" Elliott had already broken the mold for what was expected for a female rapper as an uber-talented quadruple threat singer/rapper/producer/songwriter while being carefree, plus-sized black woman who proudly owned her femininity and audacious sense of sexuality. At a time where most female rappers were expected to appeal to the patriarchal gaze and be side additions to their male counterparts, Missy not only stood as Timbo’s equal, she became a musical superstar all in her own separate context.

Sonically, she, Timbaland and the Blackground Records roster (Aaliyah, Ginuwine, Playa, et. al.) influenced the R&B landscape prior to 1999 (as Missy and Timbo proudly proclaimed on the opener "Beat Biters"). This time, in the face of adversity, Missy would come back even louder, sharper, and more unapologetic than before, earning her rightful title as the (other) Queen Bitch of Hip-Hop and R&B with Da Real World.

From its core sound to its overall tone, the album was an aggressive and non-compromising shift from Supa Dupa Fly. While Missy’s debut stood out a carefree, bouncy, and fun romp, Da Real World carried an increased and appropriately measured seriousness in its dark, futuristic and polished production, matured content, and overt political nature with her controversial and defying reclaiming of the word "bitch" without being too heavy-handed. Fans received Missy at her most unapologetic at the time while still having a fun, focused and eclectic body of work.

Reclaiming the word "bitch" wasn’t a new concept in pop or black music culture at the time: Evolving from Queen Latifah and Salt-N-Pepa’s lyrical stances against the word "bitch" and its derogatory context, female artists began to empower themselves and claim their own narrative by taking the word back.

Throughout the late '90s, rappers like Lil' Kim and Trina challenged the negative connotations and redefined it on Hardcore and Da Baddest Bitch, respectively, while Missy herself alluded to the theme on Supa Dupa Fly. That same year, in 1997, Meredith Brooks released the defiant radio anthem, "Bitch (Nothing In Between)," which went on to become one of the biggest smash hits of that decade, not to mention a defining song for a cultural revolution among women.

Upon its release, Da Real World expanded on Brooks' concept in a broad and direct fashion. Her lead single, "She’s A Bitch," where she raps, "She's a bitch/ When you say my name/ Talk mo' junk but won't look my way/ She's a bitch/ See I got more cheese/ So back on up while I roll up my sleeves,” shows Missy reclaiming the word for the sake of empowerment, rallying against the double standard of male hip-hop artists being allowed to be aggressive and assertive while female rappers were, even to this day, expected to err on the side of demure.

Missy was well aware of the double-standard at the time, telling Interview Magazine, "Women are not always taken as seriously as we should be, so sometimes we have to put our foot down. To other people that may come across as being a bitch, but it’s just knowing what we want and being confident. If I’m paying people and they’re not handling my business right, I have to check them."

"For a guy, though, it’s just considered aggressive," she continued. "You don’t hear people call males 'bitches.' But I’ve heard that people talk that way about Chaka Khan. And Aretha Franklin: If it was cold in the studio, she’d put the mike down and leave. Someone who sees her act like that may say, 'She’s a bitch,' but she just means business when she says, 'Yo, please have the heat up when I get here.' Of course, nobody’s gonna call her a bitch to her face. But I hear makeup artists all the time saying, 'Oh, I had to do such-and-such’s makeup. She’s a bitch.'"

Era contemporaries were likewise eager to join in the conversation. On the smooth "Throw Your Hands Up (Interlude)," Lil' Kim bluntly brought its significance home when she proclaimed, "Ya see 'bitch' is a strong word and only strong bitches can use that muthafuckin’ terminology. Bitch! I mean if u can't wear the name, then don’t try to use it."

From her music videos to her physical appearance and fashion, Missy re-invented the wheel she had already re-invented after shedding pounds due to a health scare while going for an edgier and space-age look which was inspired by her then-favorite film at the time and cultural juggernaut, The Matrix. The videos for Da Real World only amplified the album’s dynamite sound and themes by bringing the explosive songs to life.

Starting with the visuals for "She’s A Bitch,” Missy's one-of-a-kind, highly animated treatments (often directed by Hype Williams) were still as outlandish as they were with Supa Dupa Fly, but edgier without sacrificing any of the charm that drew the masses in the first place. For example, the two million-dollar video for "She’s A Bitch" was a more dynamic contrast to the mellow and trippy treatment for "I Can’t Stand The Rain." Instead of a "trash back," Missy donned a fearsome, all-black outfit and even painted her face the same color amid a semi-apocalyptic landscape.

Meanwhile, the electrifying “Hot Boyz (remix)” was given the hip-hop Evel Knievel treatment with Missy in her glitzy racing outfit amid a burning, exploding structure. Those visuals in particular made a lasting impression on young millennials who grew up watching the beloved 24-hour music video channel, The Box.

While the music itself did not step any further outside, well, the box, compared to Supa Dupa Fly (and one could argue that sonically, the ambition is a bit stagnant), Da Real World still displayed her extraordinary versatility as Missy travels seamlessly through between hip-hop and R&B. Deep cuts like the dancehall-driven "Mr. DJ," "Stickin’ Chickens," and its chart-topping single, "All In My Grill," sound as exciting, slick, and organic as Supa Dupa Fly’s "Best Friends" and "Sock It 2 Me." And lyrically, there’s a healthy array as broad as a Wingstop platter of intense flows and bars ("Beat Biters," "Hot Boyz"), immersive concepts, ("You Don’t Know"), honeyed melodies, and twerk-friendly bangers.

While veteran music critics like Touré made a valid point, that Missy comes off as "unfocused lyrically," as her own bars don't necessarily outshine any of her world-class hip-hop collaborators, her over-the-top delivery, flow, clever, and easily infectious songwriting made up for that. She even admitted her own weakness in her raps in the previously quoted piece with Interview.

"The rapping is cool, but my lines aren’t all that fly. People like Biggie Smalls or Jay-Z who say stuff that you have to rewind and listen to twice and be like, 'Wow, what made them say that?' or 'I would have never thought about saying that'—those are rappers I really look up to. As far as flows, I can give you flows all day," she explained.

Da Real World, on its 20th anniversary should be a cherished hip-hop and R&B album for not only its ultra-polished, futuristic sound, but in its strong collaborations. Besides the memorable battle-of-the-sexes features from the returning Lil' Kim, Da Brat, and Aaliyah, along with vets Lady Saw, Big Boi, MC Solaar, Nicole Wray, Nas, and Redman, Da Real World hosted some extremely rare collaborations with a handful of the hottest and soon-to-be impactful rookies, including Juvenile, B.G., Lil' Mo, Eminem, Eve, and an emerging solo Beyoncé (Nas and Eve were only guests on the Hot Boyz remix, released separately from the album).

The lineup of then-newcomers was—and still are—special on Da Real World due to few circumstances. As one could tell, Lil Mo, Eve, Bey were individually poised for stardom, as Mo had a scene-stealing presence throughout on songs like the single "Hot Boyz" and the compelling drama "You Don’t Know." Eve was featuring on the "Hot Boyz (remix)" and the (literally) explosive video a few months prior to her solo debut Let There Be Eve dropping, and the former Destiny’s Child lead joined Missy on the spellbinding duet "Crazy Blessings."

In Juve, B.G, and Eminem’s case, not only did it shine a brighter light on them, but "You Can’t Resist" and "Busa Rhyme" would have them flexing their most savage lyrical chops outside of their Mannie Fresh and Dr. Dre, (respectively) padded comfort zones as they were brought into Timbaland and Missy’s ultramodern soundscape.

Missy even recalls a story of how she ended up reaching out to Em in her 2014 interview with Billboard.

"[Eminem] hadn't even came out with 'My Name Is' yet. I heard something of his and instantly told Tim, 'I need this guy on my album.' Immediately when I heard him rap I thought, 'He's special.' I had the label reach out to [Dr.] Dre. He did it (his verse). I heard it and thought, 'Oh, he's going to blow up,'” Missy recalled.

Of course, for all of its progressivism, Da Real World is not without problematic moments. While Eminem deserves a ton of credit for his hungry performance on "Busa Rhyme," in hindsight, lyrics like, "Spit game to these hoes/ Like a soap opera episode/ And punch a bitch in the nose til her whole face explodes/ There's three things I hate/ Girls, women, and bitches" don't age well in 2019. (Remember, at the time such controversial lyrics were only seen as “artistic expression” within the community itself.)

Despite its rocky start, peaking at No. 10 in the Billboard 200, amid steep competition from mainstream pop blockbusters like Britney Spears' debut ...Baby One More Time, the Wild Wild West soundtrack, and albums from Ricky Martin, Backstreet Boys, and Limp Bizkit, Da Real World still went platinum, selling over one million units.

Whatever its response at the time, Da Real World should be recognized as a body of work that stood both on its own and apart from the pack of late-'90s production gloss that, all too often, masked artists' true talent. If anything, Missy's abilities as a storyteller, an unapologetic songbird, and a club maestro, combined with Timbaland’s world-breaking production, only helped set the stage for her third album, Miss E…So Addictive. 

Da Real World was and remains an important album from the '90s for its songs and visuals that continue to be adored and cherished by hip-hop fans everywhere. And while it was made at the end of the millennium, it was clearly built to last multiple eras through its sonics and overall theme of being the baddest "bitch" possible. And in that goal, it succeeded.

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