There’s a t-shirt and a meme that began circulating in the 2020s, stating, “I am my ancestors’ wildest dreams.” And even though 22-year-old rapper Monaleo isn’t a literal descendant of Ms. Lauryn Hill, she is something of a beneficiary. The Houston rapper first discovered the Fugees legend’s classic debut, The Miseducation of Lauryn Hill, at eight years old when she heard “Tell Him,” the album’s closer that can play as both a love song to a romantic partner and an ode to God. Monaleo’s mother had the song on her MySpace page and would spin the entire record while cleaning the house.

In Monaleo’s own art, she employs healthy amounts of both rapping and singing, which Ms. Hill pioneered. And as an adult, she began to resonate with “To Zion,” a power ballad dedicated to motherhood. Monaleo recorded her first album while pregnant — ironically at the same age as Hill. “I would play [that song] over and over, and it really got me through pregnancy and recording,” Monaleo told BET on a recent call. “I was able to dissect the whole body of work from a different viewpoint. Just her talking about her experiences and the different pressures, people telling her that maybe it wasn’t a good idea — I could relate to that at the time.”

As a youngster herself, then 23, Ms. Hill was as prodigious as they come. The East Orange, New Jersey native had teamed up with rapper/producer Wyclef Jean and rapper Pras to form The Fugees, and while their 1994 debut Blunted On Reality lacked originality compared to their contemporaries, its follow-up, The Score, would become one of the genre’s definitive records, both in that era and in the decades since. The trio created a sound that drew inspiration from hip-hop, ’70s soul, and reggae, using each genre to craft something new altogether — and while penning lyrics that documented the Black experience with just as much dimension, rapping about racial profiling and the desire to discover their ancestral lineage.

Wyclef rapped in addition to showcasing musicianship as a guitarist and pianist. Pras brandished rhymes and business acumen. And Lauryn was the star of the show, darting sharp, unshakably confident rhymes and a powerfully gorgeous singing voice. “Ready Or Not” saw her perform a haunting interpolation of a Delfonics chorus one moment and “defecating microphones” the next. On “Killing Me Softly,” she sweetly harmonizes the lyrics of Roberta Flack’s 1970s song of a similar title, before delivering soaring vocals on the song’s bridge. An ambidextrous approach to rapping and singing would become all but the industry standard in the 2010s and 2020s, but when Ms. Hill was doing it in the mid-’90s, it was virtually unprecedented. Between her performance on The Score and her budding acting career — she had a standout role in the hit film Sister Act 2: Back in the Habit, alongside Whoopi Goldberg — she had proven herself as one of the brightest stars in entertainment.

The Miseducation of Lauryn Hill may be the more celebrated record, but The Score was a classic in its own right: it sold seven times platinum, won the second-ever Best Rap Album with records by 2Pac, A Tribe Called Quest, and LL Cool J as competition, and it became a blueprint for hip-hop artists in the years after who were willing to try something different.

But hip-hop took a sharp turn in the two years after The Score. The genre had already begun to harness its commercial potential with success: Puff Daddy’s Bad Boy Records was pairing glitzy videos and catchy hooks with street messaging; Death Row Records was elevating gangsta rap with g-funk production on the West Coast; Nas had abandoned his street poet image from Illmatic for a new mafioso persona named Esco on his sophomore album It Was Written; and New Orleans’ No Limit Records was beginning to make inroads in the South, seemingly releasing a new album every other week. And while the genre had its share of talented women, most of the attention was going toward the likes of Lil’ Kim and Foxy Brown, who specialized in raunchy raps that allowed them to freely express their sexuality. While the new music made for a good time on the radio and at parties, many dedicated hip-hop and soul heads feared that the Black music was being diluted from what made it so special, both sonically and substantively.

Producer 9th Wonder (Jay-Z, Destiny’s Child, Erykah Badu) recognized the divide while attending North Carolina Central University and North Carolina State University in the mid-’90s. “There was a shift in the culture, where you had a lot of people falling out of love with the sound of the music,” he says. “Either you were in love with No Limit and what everybody was doing from New Orleans, or you weren’t. You had to choose a side.”

There were certainly alternatives: Rawkus Records launched the careers of acts like Yasiin Bey (formerly known as Mos Def) and Talib Kweli, whose empowering, sociopolitically-angled rhymes and boom-bap production were the antithesis of the hedonism that was taking over radio. And records like Erykah Badu’s Baduizm and D’Angelo’s Brown Sugar began to build a foundation for the genre that would later be labeled neo-soul. But those had relatively niche audiences compared to their peers' titanic presence on the airwaves and at clubs.

Ms. Hill’s quest as a solo artist soon began to tip the scales. While hip-hop was going through changes, she was going through major shifts in her life, too. She was pregnant with her first child, conceived from her relationship with Rohan Marley (the son of reggae pioneer Bob Marley), and was reeling from the professional and romantic breakup after a combustible affair with Wyclef Jean. She would later share in a documentary that she had begun to write and produce songs she planned to give to other artists, but she eventually realized she was telling her own story. She began to create her solo debut, largely recording at the Marleys’ Tuff Gong Studios in Kingston, Jamaica.

The first taste the public got of what Ms. Hill had to offer as a solo act was “Lost Ones,” a boom-bap record that sees her weaving between straightforward Newark shit-talking and Jamaican patois to deliver a scathing, three-verse takedown of an ex who mistreated her and dragged her name through the mud. “Never underestimate those who you scar / ’Cause karma, karma, karma comes back to you hard,” she warned. 9th Wonder was ecstatic: he had a song that appealed to the hip-hop aesthetics that he loved and also had mainstream accessibility.

“Mos Def and Kweli are Black Star was not on the same platform as Lauryn Hill's ‘Lost Ones.’ When it’s on the platform, everybody can find it. When it's not, that’s when it gets the underground label more than anything else,” 9th explains. “I was excited about the fact that we got a boom bap record on a major release, because we were devoid of that. So while everybody enjoyed the song and I did, too, I was elated that the sound I loved from the early ’90s was still viable.”

While “Lost Ones” was a straightforward rap record, Miseducation spread her wings even further than they were on The Score. As a member of The Fugees, she used the major stage to showcase her talent and have fun with her groupmates. But on her solo album, she had a story to tell. She navigates heartbreak with vulnerability, resentment, and despondentness on songs like “When It Hurts So Bad” and the Mary J. Blige-featured “I Used To Love Him,” singing about losing herself in her relationship before seeking spirituality to recenter herself. It makes the bliss of new love on “Nothing Even Matters” with D’Angelo feel deserved. “To Zion” is a moving account of her first pregnancy: trepidation around the impact that it could have on her career, a powerful encounter with an angel that helped convince her to keep the child, and euphoric gratitude after holding her newborn son in her arms.

And even though “Doo Wop (That Thing)” suffers from poorly-aged respectability politics around sexuality and beauty products in its quest to tell people to love themselves, credos like “how you gon’ win when you ain’t right within” are timeless. Ms. Hill outlined her mission with the album in an interview with Rolling Stone: “I think my intention was simply to make something that made my foremothers and forefathers in music and social and political struggle know that someone received what they’d sacrificed to give us, and to let my peers know that we could walk in that truth, proudly and confidently.”

But, again, the messages only matter if the music jams — and Miseducation had substance that you could groove to. “Doo Wop (That Thing)” peaked at No. 1 on the Billboard Hot 100 chart, with “Everything Is Everything” and “Ex-Factor” earning top 40 spots as well. The album would eventually sell over 20 million copies, making it one of the best-selling records of all time and, most recently, the first album by a woman rapper to go diamond. The success continued at the Grammy Awards, where Ms. Hill earned ten nominations — the most that a woman had ever been nominated for — and took home five trophies, including the coveted Album of the Year Award.

Producer Tricky Stewart (Beyoncé, Ciara, The Dream) told BET that while listening to Miseducation when he was younger, he wasn’t nearly as invested in the lyrical substantiveness as those who were disenchanted by what was on the radio. “I didn’t feel like I was being beaten over the head [with a message],” he says. It had to sound good, above all else. “She sang like a Black girl who went to church, but it sounded street. It wasn’t pretty and beautified like some of the records that I also liked at the time, like what Toni Braxton or Whitney had done in the past. This was a different voice with a different type of soul. Every element of this album, I was creatively fed.”

9th Wonder remembers the album resonating with his college class, standing on its own with all the great albums that came out before it that year and those released in the months after. “It’s playing out of every Black woman's room, bro. Like every Black woman,” he declares. “We’re listening to it on a college campus, when men and women are trying to figure themselves out. Middle of relationships, middle of hardship. So now the album brings on a different meaning at that point. You’re living it as she’s talking about it.”

“Look at what we’re encompassing: her instrumentation, her singing, her rhyming,” he continues. “If I missed the feeling of [Stevie Wonder’s] Songs In The Key of Life, I can listen to this album. If I missed what MC Lyte and Queen Latifah were doing, I can listen to this album. If I missed the social commentary in music, because we were lacking it at that time on a mainstream basis, I can listen to this album. If I miss what Nina Simone was giving us, I can listen to this album. That covers 30 years of people, easy.”

In 1998, shortly after the album’s release, four musicians — Vada Nobles, Rasheem Pugh, Tejumold and Johari Newton — filed a lawsuit against Hill. The liner notes listed each of them as instrumentalists, but all four sought additional co-writing and co-production credits for 13 of the album’s 14 tracks. “There was label pressure to do the Prince thing — written and produced by,” producer Che Pope, who also contributed to Miseducation, told Rolling Stone. “I still love you like a sister, but you didn’t do it on your own.” Hill settled with the group, known collectively as New Ark, in 2001 out of court for undisclosed terms.

Stewart says he still respects Ms. Hill’s artistry and appreciates the album but admits that the lawsuit made him see Hill differently. “I didn’t really know all the details, but if you contribute to things, your name should be present on it,” he stresses. “That doesn’t take anything away from the artists to have people help them achieve their goals sonically and musically. But Prince Roger Nelson, Rick James, El DeBarge, Brian McKnight, Babyface, Stevie Wonder — [these are] people that go in the studio by themselves, and come out with magic.”

9th Wonder has a different take. He’s careful to emphasize that anyone who contributed to the album should get proper credit and compensation, and insists he doesn’t know the details of who did what since he wasn’t there. But he dislikes the idea of Ms. Hill being penalized for things other artists and executives have not. Even if New Ark deserved more acknowledgment, he says, no one else had the perfect storm of talent, fame, and vision to pull it off the way she did. “White men have been doing this forever. Let’s start there. So now it’s a big problem if a Black woman has done it,” says 9th. “No matter how high or how well a Black woman has done something, here comes somebody who’s still trying to discredit what she’s done.”

He calls it a moot point. “There may have been a skeleton piece there [from collaborators],” he adds. “But as they say: ‘Make another ‘Hov.’ Who else has the beauty, the fashion, the voice, the singing and rapping, the style, the charisma to pull that off?”

Ms. Hill hasn’t released another studio album since Miseducation; only a live album, MTV Unplugged No. 2.0, which suffered critically while building a cult following of supporters. Her life since then has been a combination of legal issues, sporadic singles, and performances that have had fans complaining about her tardiness. But the legacy of her classic debut lives on. Her blueprint of employing both rapping and singing with equal deftness has become an industry norm, and in 2023, women have blown hip-hop open to express themselves in a wider variety of sounds, styles, and looks than the genre has ever seen before. That growth doesn’t happen without Ms. Hill’s work.

Professor 9th insists that Miseducation of Lauryn Hill doesn’t simply belong in the conversation with other women’s rap albums but with iconic albums across all genres of Black music.

“I can name the albums in history during my lifetime that became walking anthems for women,” he says, breaking down a list of less than a dozen records that includes Anita Baker's Rapture, Whitney Houston’s self-titled debut, Janet Jackson’s Rhythm Nation 1814 and Control, and TLC’s CrazySexyCool, among others. “These are staples. And out of all those albums, I have never seen one galvanize a generation of Black women more than The Miseducation of Lauryn Hill.”