“Have you ever had a dream, Neo, that you were so sure was real?” It’s Act 1 of The Matrix, and Morpheus is laying out the rules of reality for Keanu Reeves’ phlegmatic protagonist, offering him a choice. Neo slowly touches a mirror, liquid silver creeping up his arm, engulfing him, ripping him from the simulated life he experienced as reality and into the “real” world—an AI-controlled, post-apocalyptic Earth. The Wachowskis’ universe of brain-link tech and teleporting phone booths warped everybody’s perceptions of reality back in 1999. Now, imagine Missy Elliott watching it for the first time. It was a mindfuck, even for an artist with a similarly twisted, futuristic approach to her craft. Just like that, she’d found a framework for her second album.

By that point, Missy had proven herself a hip-hop anomaly in a rapidly digitizing world. Early Y2K radio was largely iterative of the envelope-pushing sound she and Timbaland created on her 1997 debut, Supa Dupa Fly. That album, along with the staccato beat-box rhythms on Aaliyah’s One in a Million, made the Virginia duo stand out in a sea of samplers, establishing them as the industry’s sci-fi oddballs crafting out-of-this-world, pop-savvy tracks. Pop music suddenly sounded like a dial-up internet connection on the fritz, with R&B acts like Ginuwine, Total, SWV, and 702 serving as smooth ciphers for Missy and Timbaland’s wildest ideas. In the wake of other producers cribbing their style, Da Real World was a chance for Missy to halt the assembly line and build her mythos, drawing directly from The Matrix. “I am Morpheus,” a screwed voice (presumably Timbaland) slurs on the album’s intro to remind people (as if they needed to) that he and Missy could constantly shift reality.

Though darker in tone and less whimsical than Supa Dupa Fly, her second album is driven by the same fluid melodies and myriad flows, with many of the beats sourced from sounds Timbaland collected after a trip to Japan. The Matrix framing is mostly smoke and mirrors here, peppered lightly in interludes throughout. But the movie’s key premise—the idea of transcending binaries—likely resonated with Missy and aligns with this project’s theme of women breaking free from reductive labels. In interviews for Da Real World, Missy often highlighted a double standard that feels cliché today: aggressive men are seen as bosses, while women of the same ilk are dismissed as bitches or divas. The self-proclaimed shy girl also spoke about tapping into “bitch mode” herself to get things done. Da Real World is her own personal rebellion, her egalitarian playground where she can flex alongside her male peers (Big Boi, Eminem, Redman, Juvenile, BG), claiming equity in the game while leaving room for women in her orbit (Lil Mo, Aaliyah, Lil’ Kim, Da Brat, Lady Saw, Nicole Wray) to air their frustrations over a Timbaland beat.

The pop world was then caught up in the bubblegum rapture of teen idols, Spice Girls, and sticky R&B kiss-offs—two of 1999’s biggest hits were TLC’s “No Scrubs” and Destiny’s Child‘s “Bills, Bills, Bills.” Some in the industry labeled those two songs “male-bashing anthems,” but really, they showed women demanding emotional reciprocity and equity, in addition to paying their automo-bills. Pop music was newly flush with women performing their ideas of feminism for mass appeal, sending the empowerment category toward its inevitable nadir. Missy’s approach was to verbalize the biases and bullshit women everywhere felt from a less glossy, more street-level angle while making space for playfulness and contradiction. Her songs unspooled like soapy, engrossing beauty shop confessions starring imperfect women. She told Rolling Stone in 1999, “Women seem strong in [my] songs because that’s not just a song anymore. This is what we experience in everyday life, in business, relationships, whatever.”

Coming off the success of her debut, Missy originally wanted to title her follow-up She’s a Bitch, but mainstream audiences were still contending with the term, and the big-box stores that would be selling the album were wary of it. By then, “bitch” had gone through a linguistic odyssey in rap, with Queen Latifah outright rejecting its derogatory use, only for Lil’ Kim and Foxy Brown to later reclaim the word with conviction, ushering in the era of the bad bitch. The landscape had finally expanded, allowing for a broader spectrum of voices like Eve, Da Brat, and Trina, the latter of whom decisively used “bitch” in her debut solo single and album title. And in the two years between Supa Dupa Fly’s release and Da Real World, another superstar rapper-singer emerged—Lauryn Hill, whose music spoke directly to the complexities of Black womanhood. Even with all this range among women MCs, the industry at large was still confining them to binary roles. Rapper Cormega said in a July 1999 interview, referencing Missy and Lauryn, “A lot of female rappers were just trying to sell their bodies. But these two women emphasize themselves more.” Missy’s take was that this contrast—that a woman MC could only be sexy or thoughtful—was a fiction, a part of the simulation she could transcend.

In interviews for Da Real World, Missy spoke openly about how her upbringing in Portsmouth, Virginia, influenced her view of what it means to be a woman in the world. She described the trauma of seeing her father abuse her mother, Patricia Elliott, who became a single parent when Missy was 14. “Watching my mother move from being totally dependent on my father to getting out there and working‭ and doing whatever she had to do to survive and keep me happy makes me realize how strong she was,” Missy told Essence in 2000. Patricia’s struggles turned out to be an early catalyst for the fury that fueled her daughter’s creativity. Timbaland—who met Missy through a mutual friend, the late rapper, Magoo—instantly saw her as an alien equal. “I could tell she was taking it all in, every instrument, every layer of sound. She was pulling the music apart and putting it back together in her head—the same way that I did,” he recalled in his 2015 memoir.

Da Real World is as much a testament to Missy’s tastemaking prowess as it is a bold solo statement, her voice sometimes overshadowed by a star-studded lineup of established and rising acts. Eminem characteristically hijacks two out of three verses on “Busa Rhyme” with his nasally Slim Shady antics, trampling over Timbaland’s chomping King Kong drums. The Detroit rapper was then still ascending from the mixtape scene on his way to becoming pop’s official edgelord. To say the least, his shock bars—“Punch a bitch in the nose ’til her whole face explodes”—sound jarring next to Missy’s male-directed venom, and yet Em’s star power on the song is, maddeningly, undeniable.

Redman makes a more palatable turn on “Dangerous Mouths,” a greasy track where Missy bounces off his bombastic energy, riding Timbaland’s doomsday drums. For the most part, the fun that powered Supa Dupa Fly takes a backseat in favor of a more intimidating sound on songs like “U Can’t Resist,” where Missy’s rapid-fire flow sounds smooth and composed alongside Juvenile and B.G.’s syrup-thick drawls amid slasher-film strings. The similarly haunting second single, “All N My Grill” plays like a hip-hop opera featuring Big Boi; it’s among Timbaland’s least exciting beats but still one of Missy’s most memorably plainspoken hooks, a lilting request with backup vocals from Nicole Wray: “Can you pay my bills?/Let me know if you will/’Cause a chick gotta live.”

With Missy, a hit song is less about elaborate bars and more about experimenting to find a flow that slides right into the grooves of Timbaland’s tracks until she reaches a sound both accessible and Out There. She’s explained that she tends to write the way she speaks, not in song form, and rarely with intricate lyricism in mind. That method works phenomenally on the album’s lead single, “She’s a Bitch,” a pure flex session where Missy gets to talk her shit, flipping from chill to aggressive over a beat that could break up concrete, tailor-made for Missy’s pithy threats (“I’ma give your body to the sky,” and so on). It’s the song that best bridges the album’s core themes of trash-talking and self-empowerment. Again, she’s speaking for the tribe here, repurposing the word “bitch” as a means to control her reality. In a preceding interlude before the song, Lil’ Kim evangelizes, “See, ‘bitch’ is a strong word, and only strong bitches could use that motherfuckin’ terminology.”

Often in these songs, Missy seems to be speaking on two levels. On first listen, her bars are witty and literal; listen again, and a more complex or contradictory message might surface. Even if the pop mainstream wasn’t quite ready to understand feminist nuance, this multifaceted approach implicitly demonstrated that there isn’t one single, obvious way to be feminist. “Hot Boyz” reads like a straightforward celebration of street dudes with fat wallets and luxury rides. Beneath the fun club vibe, though, you could read Missy’s whispery tone (“Is that your car? The XK8?”) as subtly mocking the guys desperate for a woman to be impressed by them. (The superior remix featuring Q-Tip, Eve, and Nas—a multidimensional posse cut—is sadly not the official album version.) “You Don’t Know,” about being tangled in a rivalry with another woman over a guy, might seem at odds with Missy’s usual stance of holding men accountable. Again, she shows a layer of self-awareness in the intro, pointing out that when it comes to cheating, men get to settle their differences and laugh it off, while women are seen as possessive and territorial. Later, Missy brags, “You been sucking his dick, tasting my clit.” The song comes across as theater.

“Stickin’ Chickens” takes on the opposing side of the drama—fierce loyalty among women in the face of trifling men. Aaliyah quietly smolders on the track, while Da Brat’s explosive verse swings between resentment and vulnerability: “Scared to set foot in another relationship ’cause of the heartache,” she raps. This is All My Children for millennial women sporting blazers in the club, the same brand of mess that makes even the most cringe-worthy reality TV so ingestible.

Between Missy’s breakout debut and the explosive, clubby Miss E… So Addictive—home to some of her zaniest, most inventive dance records—Da Real World’s story often gets lost. It didn’t match Supa Dupa Fly’s rapid success or hit singles and took eight months to go platinum (compared to two for her debut). But this album is where Missy honed her Afrofuturist vision and world-building skills while advocating for women to seize control of the language used to define them. It wasn’t until decades later that the Wachowskis, both trans women, acknowledged The Matrix could be interpreted as a story about the experience of being trans—in other words, that the film itself could be read as a complex expression of womanhood, and that making the movie was a way for the directors to reshape the world as they saw it. The Matrix theme on Da Real World, then, continues to be apropos: a reflection of Missy’s commitment to exploring new sounds and concepts, bending reality toward her eccentric vision until everyone else realizes there is no spoon.