Pittsburgh Celebrates 20 Years of The Miseducation of Lauryn Hill

The impact of The Miseducation of Lauryn Hill, Lauryn Hill's 1998 debut (and only) solo album, has grown large in the cultural consciousness of hip-hop and R&B in the 20 years since its release. It was almost immediately canonized as a classic first album, with Hill possessing a laser-focused sense of purpose and delivering a stark and beautiful personal journey buoyed by a virtuosic display of talent (my god, that voice), mastery of genre (hip-hop, neo-soul, reggae, folk music), and her Haitian heritage on proud display. Miseducation is a landmark album because it's a world until itself, with Hill the center of gravity, pulling listeners along through her story with passion and care. 

As an executive producer, as a rapper, as a singer, Hill's work on Miseducation remains unimpeachable, but the album also serves as a bittersweet time capsule of a career that only seemed to be going in one direction. But as we know now, Hill hasn't released an album of new material since Miseducation, and has ghosted in and out of the public eye over the last two decades—reportedly due to the pressure of ever growing fame and dissatisfaction with the record industry—with only a few stray singles and a long line of mercurial live performances and cancellations left in her wake. Whether it's fair or not, Hill's turmoil has only added to the outsized myth that surrounds the record. 

But now, on the 20th anniversary of the release of The Miseducation of Lauryn Hill, we've asked several WYEP contributors, local musicians and music writers to reflect on and celebrate their favorite songs, paying homage to one of the most important albums of the 1990s.  Patrick Bowman

"Doo Wop (That Thing)"

One of my favorite songs on The Miseducation of Lauryn Hill  is “Doo Wop (That Thing).” This lead single received a lot of radio play before and after she released the project. I remember many car trips being mesmerized by the production. I was 6 years old when this song was released; however even then I was drawn initially to the beat and instrumentation. As I grew older and more aware, I would listen to the record through new ears.  I slowly began to realize the significance of the lyrics. The song presented words of caution and perspective when dealing with matters of the heart. Through this song Lauryn taught us to look past facades and material things and encouraged us to see a lover’s true intentions. Navigating through the emotion of love for anybody is complicated.  This record served as an eye opener and guide. — Kai Roberts


Hearing this album in 1998 is what made me a fan of Lauryn Hill. There are a few songs on the album that really hit home for me, one of them being "Ex-Factor," a song that she supposedly wrote as a reflection of her relationship with Wyclef Jean, a member of The Fugees. I would play this song on repeat, riding around East Liberty and the Hill District singing my little lungs out and feeling like I connected with this song on such a deep level even though I was only 19 at the time and couldn't really claim having any actual, meaningful relationships. However, that first line "It could all be so simple. But you'd rather make it hard" is something that most people can identify with. We have all been in a relationship where we just felt the other person wasn't "getting us" or that we weren't being heard or understood, but at the same time we may not have been ready to completely abandon the situation. Lauryn's raw emotions always come through loud and clear in her work, but this particular song is one that will hit you right in the core. Being a hip hop artist, I also feel like this song can be applied to the love/hate relationship I have had with the genre over the last 20 years or so. Dear Hip Hop: "No one loves you more than me. And no one ever will." — Hollyhood

"Lost Ones"

Ostensibly the album opener (save a short, classroom-tinged interlude) "Lost Ones," with Hill immediately declaring "Funny how money change the situation," is an unforgiving punch in the mouth, especially considering most fans who purchased the record were lured in by the groovy neo-soul inflected hip-hop of lead single "Doo-Wop (That Thing). Hill cooly unspools tightly coiled verses of venomous bars--allegedly aimed at ex-lover and former bandmate Wyclef Jean--over sparse, pulsating keyboard samples, kick drums, and record scratches, dipping in and out of a Caribbean patois as she goes. It's a neck-snapping re-introduction to say the least, solidifying Hill's bonafides as a truly fearsome MC ("My emancipation don't fit your equazaaan," is a phrase I think about on a weekly basis) while putting one of the biggest hip-hop stars in the world, and the most toxic person in her life both professionally and personally, on blast with her first words on the record. Ms. Hill, we salute you. — Patrick Bowman (WYEP Contributor/Speed of Sound)

"To Zion"

The Miseducation of Lauryn Hill is turning 25 this year on the day after my birthday. This album served as one of the soundtracks of my childhood, but the song that stands out among them all to me is "To Zion". Not only is this my mother’s favorite Ms. Lauryn song but it's one of the most emotional on this album. It tells the story of a young Lauryn Hill who is has just found out she's pregnant and now is faced with the challenges of raising a child and continuing her then budding career. She speaks about how others told her to get an abortion and instead she chose to follow her heart and have her son. This song sticks with me because its a story that mirrors that of my own mother and I hope it sticks with you all in the same way. —Barz Blackman (of BB Guns)

"When It Hurts So Bad"

When someone as soulful as Hill takes on a tried-and-true topic like heartbreak, the pain makes the notes vibrate as much as her vocal cords do. The subtle, midtempo groove on “When It Hurts so Bad” mirrors Hill moving through the emotional aftermath of loving a man who “wasn’t even concerned.” A pronounced bassline, textured percussion, floating background vocals, fingerpicked guitar, and harp strums frame Hill’s voice. Even in her wounded state, she moves, she speaks—she isn’t stagnant. And her vocal runs shine—remarkable and clean but drawing from something obviously raw and real: valleys of lament (“I loved real, real hard once/but it wasn’t returned…”), peaks of anguish (“Gave up my power/I existed, for you…”), and the introspection in between.

At this midpoint of her Miseducation, it makes sense that some lessons need learned the hard way. “When It Hurts so Bad” is strikingly vulnerable. It’s mourning in motion, and it’s gorgeous. Melanie Stangl (Sound Scene Express)

"Every Ghetto, Every City"

The Miseducation of Lauryn Hill is a milestone album in the history of hip-hop. Ms. Lauryn Hill tastefully fused rap, R&B, and neo soul in this project. "Every Ghetto, Every City" is a tribute to Lauryn Hill's hometown, South Orange, New Jersey. Her lyrics descriptively give listeners a glimpse of good and bad memories growing up in a turbulent time period. Jimmy Bucek


Not only was Lauryn a prominent female force in a male-dominated field, but she was a self-actualized, spiritually, morally and existentially potent individual. She was honed into the rap game and how fake it can be. “Superstar,” an ode to being taught to be something she was not, regarded the state of hip-hop back then in way that could be applied to the state of it today. Lauryn Hill found showing a one-dimensional version of reality trivial. The chorus poetically puts this into terms very well. “Music is supposed to inspire, why aren’t we getting any higher?” As artists and people in general, we have to question ourselves and come to find comfort in expressing our truths. Aside from Lauryn’s riffing skills, one major thing I enjoyed about the album was that it fearlessly asks important existential questions. And one question I will leave you with: Would the same people who become successful for appeasing people and looking crazy, get on for their talent, lyrical abilities and hard work if all the hype were stripped away? — Lexa Terrestrial