Lauryn Hill currently sits inside a prison cell in Connecticut. The neo-soul legend is approximately halfway through a three-month sentence inside the Danbury penitentiary, located a little more than 80 miles from her hometown of South Orange, N.J., where she launched her illustrious career with the influential hip-hop trio The Fugees in the early 1990s.

On July 8, Hill reported to the minimal-security correctional facility close to one year after pleading guilty to tax evasion on $1.8 million earned between 2005 and 2007. Her incarceration marks the latest incident in a enduring string of personal problems that have included reclusive disappearances from the public spotlight, erratic performances upon returning onstage, lawsuits over proper songwriting credits, and numerous other troubles.

Despite the tumultuous, and at times mysterious, struggles surrounding the former Fugees emcee and Grammy Award winner, it’s easy to forget how much she mattered at the height of her career throughout the 1990s. She’ll be in prison still when her seminal masterpiece, The Miseducation Of Lauryn Hill, turns 15 years old on Sunday, August 25. But it’s that album, her lone studio record, which exhibited her undeniable talent and, more importantly helped propel hip-hop into the mainstream and international phenomenon that it’s become today.

On February 8, 1999, Time celebrated hip hop’s 20th anniversary by highlighting the impact of rap music and its affiliated culture in a 12-page cover story. While the publication examined the genre’s rich history dating back to the Sugarhill Gang’s 1979 hit “Rapper’s Delight,” they chose Lauryn Hill to grace the magazine’s cover. In doing so, Time effectively crowned her as hip hop’s matriarch — a decision reaffirmed weeks later when she shattered records at the 41st Grammy Awards.

Following the release of her full-length debut, The Miseducation Of Lauryn Hill, the former Fugees member broke from the ranks of her East Coast rap group to become a superstar in her own right. Hill’s enormous success as part of the South Orange, N.J., trio, followed by her stunning solo album, made her one of hip hop’s most distinguished figures toward the end of the 20th century. To put her stature into perspective, Time had only placed 17 black figures on its cover throughout the 1990s (out of 525 covers). Only five — including Bill Cosby, Bill T. Jones, Toni Morrison, and Oprah Winfrey — worked in arts and entertainment. Lauryn Hill was the only musician. She was just 23 years old.

Hill exerted a self-awareness regarding her place in hip hop following Miseducation’s resounding success. “There are kids in the audiences now who weren’t born when there wasn’t hip-hop,” she told Time. “They grew up on it; it’s part of the culture. It’s a huge thing. It’s not segregated anymore. It’s not just in the Bronx, it’s all over the world.”

It appeared back then that Hill would lead a new generation of rappers that were intent on stepping beyond rap’s explicit and misogynistic status quo, and instead emphasize personal and conscientious themes. But her career took an unexpected turn. For more than a decade, Lauryn Hill’s story essentially grew into an urban legend, akin to Neutral Milk Hotel frontman Jeff Mangum, who released his seminal album, In The Aeroplane Over The Sea, within six months of Miseducation. Both records overwhelmingly exceeded initial expectations and catapulted their careers to unforeseen heights. But for entirely different reasons, each disappeared from the public eye amid periods of heightened exposure and commercial breakthrough. Hiatuses slowly turned indefinite and the question turned to if, not when, either would ever release a follow-up record.

Like Mangum — whose creative myth and subsequent admiration helped spark indie rock’s resurgence in the following decade — Hill’s public absence transformed her perception from a cosmopolitan artist into an enigmatic musician responsible for influencing the next wave of pop, soul, and rap stars in the 2000s. Not only did musicians revere Miseducation; the album became so beloved that even some religious congregations worked her songs into their services.

“Churches were substituting God in the lyrics [for the song “Nothing Even Matters”], D’Angelo, who collaborated with Hill on that song, told Rolling Stone in 2008. “Whenever they make a gospel version from a secular song, that’s significant.”

Hill was one of the first female rappers to appeal beyond hip-hop’s initial audience as she incorporated elements of soul, R&B, and reggae into her music. She wasn’t the first person to integrate disparate sounds or styles, given that rap’s first two decades were an exercise in that creative process. Acts like Run D.M.C., Beastie Boys, and Public Enemy perfected the art of rapping over samples and beats. Old School, New School, and Golden Age artists often sampled recordings in ways that innovatively juxtaposed genres, including the Fugees. But where Miseducation differed was in its cohesive production. Hill’s album drew from the songs of classic rockers (the Doors) and heralded contemporaries (Wu-Tang Clan), recognizable singles (Labi Siffre’s “I Got The…”) and deep cuts (Sister Nancy’s “Bam Bam”). She remained rooted in older influences while arriving with a sound that was, by and large, her own.

Like her predecessors, Hill borrowed from others. But sometimes the greatest innovators aren’t the ones who construct brilliant ideas from scratch, and instead innovate through melding together different artistic statements, musical elements, and cultural messages. Without Elvis Presley or Chuck Berry, Robert Johnson probably wouldn’t be known as a precursor to rock ‘n’ roll several decades later. If Run D.M.C didn’t break though with their hit single “Walk This Way” in 1986, DJ Kool Herc likely wouldn’t be remembered as a hip-hop progenitor, and 1520 Sedgwick Avenue wouldn’t be widely recognized as hip-hop’s birthplace.

The Miseducation Of Lauryn Hill represented a watershed moment for the genre as it shepherded in mainstream acceptance with a mainstream market beyond traditional rap circles. One way to understand Lauryn Hill’s impression on late-’90s popular music is to look at her sales figures. During the week Miseducation hit shelves, Hill sold more than 420,000 copies, breaking the record for release-week sales by any female artist. The Recording Industry Association Of America certified the album Gold a little more than month after it came out, and the record spent 81 total weeks in the Billboard 200. At the 1999 Grammys, Hill set two additional records for a female artist: She received 10 nominations and won five awards.

Hill’s female peers, who included Queen Latifah, Salt-N-Pepa, and Lil’ Kim, were each influential in their own way during the ’90s. These notable early female rappers created works that would pave the way for future female emcees. They achieved varying levels of popular acclaim and carved out a legacy as forerunners responsible for breaking down the genre’s gender barriers. Hill built upon their successes as she stepped beyond hip-hop’s traditional themes and lyrics in her work. She spoke about feminism, spirituality, and other parts of her life throughout Miseducation. And in doing so, she reached new and larger audiences receptive to her honesty and intimacy.

“What Lauryn is doing is opening doors for female artists who aren’t materialistic and flashing their titties,” Wu-Tang Clan’s RZA told VH1.com about a month after Miseducation’s release. “She represents a beauty and a wholesomeness that’s more down-to-earth. She makes music that people can relate to, which is why she’s done so well.”

Hill wasn’t the first hip-hop artist to be personal, but she helped pioneer conscientious songwriting in the genre in a way that hadn’t existed before. Audiences once hesitant toward the rap’s explicit content warmed up to her heartfelt approach. On “To Zion,” Hill professed her unconditional love for her unborn son and discussed the sacrifices she made in spite of her blossoming career. She confronted failed romantic relationships on “Ex-Factor,” simultaneously acknowledging her self-worth and heartbreak. Hill preached empowerment throughout Miseducation while delving into religion, self-ambition, fame, and perspective. All along, she managed conveyed a deeper universal meaning that resonated beyond prior genre barriers.

The album had such a widespread impact that many of Hill’s sales records remained intact until 2012 when Adele broke them upon releasing 21. Adele, like Hill, similarly emphasized a substance-over-style approach and crafted a souful record that focused on her voice, complementary vintage production and universal appeal. She’s an example of one artist that has approached Hill’s levels of success. But in many other areas, Hill’s work continues to trump other female superstars that have followed. Adele has listed Destiny’s Child, Pink, and Spice Girls as key influences growing up, but she says Hill’s impression has remained most evident.

In May 2011, Adele told Rhapsody TV: “I remember [Miseducation] being huge everywhere, even though I was really young and pretty oblivious to record sales and notoriety. But for some reason, I was very aware of how successful that record was. I was a big fan of Lauryn Hill when she was in the Fugees anyway and that was a record I grew up listening to, I analyzed it for about a month at the age of eight and was constantly wondering when I would be that passionate about something to write a record about, even though I didn’t know I was going to make a record when I was older.”

It’s in this sense that Hill made the most notable impact. Looking at hip-hop’s cultural milieu near the turn of the century, Miseducation helped transform the way larger audiences perceived rap music. In 2010, NPR’s Zoe Chace interviewed a then-reclusive Hill and aptly described her influence in saying that: “The story of her voice is also the story of the generation which came of age in the 1990s.” Like Adele and Chace, I’ve never experienced a world without hip hop. In that sense, Hill’s voice wasn’t simply associated with our generation. She defined it.

Similar to the way Adele or Chace experienced the record, The Miseducation Of Lauryn Hill fully resonated with me the first time I heard the album. It wasn’t because of her outspoken stance, love of God, or devotion to her unborn baby — it was the way that she sang that captivated me. Hill cries out with such conviction that you don’t need to hear every lyric, phrase, or verse to comprehend the overlying sentiment of her songs. It’s similar to the way Tom Waits’ longs on Closing Time, Brian Wilson daydreams on SMiLE, Joni Mitchell laments on Blue or Chuck D confronts on It Takes A Nation Of Millions To Hold Us Back. Like the aforementioned greats, her efficacy as a songwriter, vocalist, and producer remains just as powerful as it did when the album first came out.

“Lauryn had that blend of toughness and soulfulness, melody and swagger,” Miseducation contributor John Legend told Rolling Stone in 2008. “She did it better than anybody still has done it. People are still trying to capture that moment.”

The moment Legend referred to in that interview has since percolated into mainstream pop, soul, and hip hop since the album’s 1998 release. One of Kanye West’s earliest nods came on his 2004 debut, The College Dropout, with his single “All Falls Down, ” a track on which he interpolated Hill’s “Mystery Of Iniquity.” In 2007, he claimed he could inherit her role as rap’s preeminent conscientious lyricist, stating in his song “Champion,” “Lauryn Hill say her heart was in Zion/ I wish her heart still was in rhymin’/ ‘Cause who the kids gon’ listen to? Huh?/ I guess me if it isn’t you.”

There’s a long list of other artists Hill has influenced. Talib Kweli wrote “Ms. Hill” about her decade out of the limelight. The late Amy Winehouse frequently included Hill’s “Doo Wop (That Thing)” as part of a medley during her Back To Black tour dates. More recently, Nicki Minaj expressed an unabashed admiration for Hill as well as disappointment regarding her inability to appear on the single “Champion,” a track off her esoteric 2012 sophomore release, Pink Friday: Roman Reloaded. Minaj, whom the New York Times music critic Jon Caramanica once called “the most influential female rapper of all time,” remains indebted to Hill’s influence.

“I wanted to get her on ‘Champion,'” Minaj told Funkmaster Flex in an interview with Hot 97 last year. “That would have been crazy, right? She was my fave … Lauryn to me is the goddess. I’d love to meet her.”

Those five artists represent a small contingency of individuals swayed by Hill, let alone the respect she garnered from her contemporaries. Miseducation included contributions from artists like Mary J. Blige, D’Angelo, John Legend, and Carlos Santana. Nas, A Tribe Called Quest, and Common have featured Hill as a guest on their records; while Eminem, Missy Elliott, Jay-Z, and Kendrick Lamar have referred to her by name in their own respective songs.

But then Hill left the public eye without explanation and slowly transformed into the enigmatic artist she’s become today. A mystifying decade followed her late-’90s ascent, self-imposed exile, and other rumored personal issues. Some believe her disappearance had to do with her growing distaste for the music industry’s business practices. Others felt she left the spotlight to focus on her motherhood and spirituality.

Rumors swirled that Hill had bipolar disorder, received spiritual misguidance, and underwent paternity disputes. She refused to do interviews for much of this period, but her disillusionment remained apparent throughout the lengthy interludes on her 2002 live album, MTV Unplugged No. 2.0. She also endured an arduous legal battle after four musicians sued her for failure to properly credit their songwriting and production on The Miseducation Of Lauryn Hill. The details of that lawsuit, which reportedly settled for $5 million, never fully surfaced. Some believe Hill caved despite her legal representation’s objections in order to put an end to a tumultuous fight. Meanwhile, her skeptics claimed she should have given those musicians co-songwriting and production credit on 13 of the album’s 14 tracks (the liner notes state that Hill was the sole songwriter on 12 tracks). Few know what truly happened, but it the tussle cast a shadow on her musical legacy.

After years of silence, Hill slowly launched a return and played occasional shows. She joined the Rock The Bells tour in 2010 to mixed fanfare and made appearances at Coachella and New Orleans Jazz Fest the following year. Along the way, critics lashed out at Hill for her erratic and unprofessional performances, including some gigs where she kept fans waiting for hours to hear a shell of her former self. Hill released occasional singles, including “Fearless Vampire Killer” and “Black Rage,” but a proper release never surfaced despite rumors that dozens of songs are finished.

The law eventually caught up with Hill’s free-spirited lifestyle in June 2012 when she was charged with tax evasion. Around that time, she explained in a Tumblr post — her primary medium for public communication — that she had withdrawn from society to protect her family’s safety amid a “climate of hostility, false entitlement, manipulation, racial prejudice, sexism and ageism.” The singer added that she intended all along to fix the situation. Nevertheless, she pled guilty weeks later in the United States District Court for the District of New Jersey and stated through her lawyers she would agree to pay back taxes stemming from the three-year period.

“During this period of crisis, much was said about me both slanted and inaccurate, by those who had become dependent on my creative force, yet unwilling to fully acknowledge the importance of my contribution, nor compensate me equitably for it,” Hill said.

U.S. Magistrate Judge Madeline Cox Arleo sentenced Hill to a three-month prison sentence, which she started serving last month. Once released, Hill will remain under house arrest for three months as part of yearlong supervised probation. Right before she headed to prison, Hill signed a $1 million contract with Sony that effectively created a new label, Observe Creation Music, and obligates her to record five new songs, followed by a new album. Whether that release ever sees the light of day remains to be seen, but given her financial situation, she may have no choice but release an album — even if it’s not entirely on her own creative terms.

But that’ll have to wait until Hill finishes her sentence. For now, she has only posted one short message to the outside world that offered a brief glimpse into her life behind bars. She acknowledged her transition from international superstar to white-collar inmate has “taken some adjustment,” but largely remained hopeful about her incarceration.

“I cannot deny the favor I have encountered while in here, and general warm reception from a community of people who despite their circumstances, have found unique ways to make the best of them,” she wrote.

It’s been 15 years since Hill helped bridge the gap between hip hop and mainstream music, and still her legacy remains tied to far more than just the songs comprising The Miseducation Of Lauryn Hill. Her magnum opus told a highly personal story while gazing into the rise and fall of one of music’s most dynamic figures. Miseducation offers a lesson on the rigors of the music industry as much as it is an amalgam for mainstream music today.

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