As the artist celebrates her LP’s 25th anniversary, we’re celebrating the raw honesty of its songs of heartbreak, betrayal and devotion
Published Oct 25, 2023
The Miseducation of Lauryn Hill is one of the greatest albums of its era. Blazing onto the charts upon its release on August 25, 1998, it remains Lauryn Hill‘s only solo album.
Hill, an artist turned cultural phenomenon, is revered by many — in particular Black women, because she boldly stood in her power with grace, perseverance and style in a world that often expects assured women to cower. At the height of her career, the 23-year-old New Jerseyite faced intense scrutiny over the breakup of the Fugees and her tumultuous romantic relationship with band member Wyclef Jean.
Miseducation is a spin on a tale as old as time (especially in R&B, soul and neo soul, a genre Hill helped solidify) — self-worth, betrayal and heartbreak. It’s an honest depiction of the duality of life, and relatable to anyone who has ever made mistakes despite knowing better.
Hill’s album sold 422,624 copies within the first week, topping the Billboard chart and breaking the record for first-week sales by a female artist at the time. In 1998, the project made the former leading lady of the Fugees the first woman to take home five Grammys in a single night, and she became the first-ever hip-hop artist to win Album of the Year.
As Hill celebrates the 25th anniversary of Miseducation with a tour alongside the Fugees, including a stop at Toronto’s Scotiabank Arena on Thursday (October 26), we’re ranking all of the songs on her classic album (not including the “Intro,” mind you). Cultural relevance as well as musical impact were considered here, plus some personal bias, of course.
15. “Every Ghetto, Every City”
This is an ode to Newark, NJ, the place Hill grew up and began her career, which is also known as New Jerusalem. It’s a light-hearted, feel-good record, riddled with nostalgia and various tri-state references, placed on an album with many grand and heavy themes. It effectively reminisces about yesteryear, but you may very well forget it’s on the album.
14. “The Miseducation of Lauryn Hill”
Hill signs off, singing with grandiose echo against piano keys and what sounds like a crackly vinyl record playing, declaring that she will no longer allow anyone to falsely define who she is or her future. Her Motown roots, and her time spent in the studio with Aretha Franklin and writing for fellow New Jersey native Whitney Houston, can be heard here. As an outro, it ties the previous 13 tracks together in a neat bow — although, unless you were playing the entire album from start to finish, it’s not a song you would likely return to.
13. “Final Hour”
“Final Hour” screams hypocrisy, but it’s another variation of Hill speaking her truth. It’s a reminder that nothing is worth your soul — not money, fame or the thrill of an affair. The message is essential and the rap cadence is effortless.
12. “Forgive Them Father”
“Forgive Them Father” is enriched with saxophone synths and fuses jazz with reggae — sounds that Hill has embraced throughout her career and continues to lean into midway through the project. Pretentious? Possibly. A tad preachy? Yes — a common thread throughout the Miseducation. But preachiness is rightfully earned here, as the song centres on the biblical readings from Luke 23:34. It plays like a woman betrayed by those closest to her, to the point where her greatest defence is to pray for those who have trespassed against her.
11. “Superstar”
“Superstar” displays Hill’s ability to call others out on their crap, disguised in a sweet melody. She’s candid and bold while sharing her unfiltered opinions on controversial topics at the time of the project — one of which was the state of rap music. As hip-hop transformed from its fiery underground roots into a commercially successful industry, it was criticized for losing its political edge. As on “Doo Wop (That Thing),” she pleads with her fellow hip-hop artists to hold the culture in the same high esteem as in the days of its conception.
10. “When It Hurts So Bad”
“When It Hurts So Bad” isn’t a standout heartbreak song, like “I Use To Love Him” or “Ex-Factor,” but it offers just as much insight on the concept of love gone sour as the songs higher on this list.
9. “Tell Him”
“Tell Him” is a hidden track that wasn’t included in the original release of Miseducation. It juxtaposes the love Hill has for a lover with the love God has for humanity. It references various biblical definitions of love, and speaks to Hill’s growth in her understanding of the kind of love she wants after all the toxic versions she has experienced. This track feels like a hug on a chilly fall day, and serves as a final reminder of self-love as an alternative ending to the quintessential love album.
8. “I Use To Love Him” (feat. Mary J. Blige)
This track features Mary J. Blige, who by this point was standing in her own lane as the “Queen of Hip-Hop Soul.” Hill and Blige grapple with the intensities of emotional agony and the evident mistakes they’ve made along the way. The duet displays chilling vocals, identifiable to women who have overlooked themselves to appease their partners and can now express themselves, free of toxicity.
7. “Everything Is Everything”
“Everything Is Everything” was one of the three leading singles, alongside “Doo-Wop (That Thing)” and “Ex-Factor,” that earned Hill another Top 40 spot on the Billboard charts. L. Boogie flexes her rap prowess on this catchy tune to uplift listeners — especially the youth to whom she dedicates the record — to have faith in a better tomorrow.
6. “Nothing Even Matters” (feat. D’Angelo)
Nearing the end of the project, Hill tag-teams with D’Angelo, a fellow neo-soul artist who by this point was a critically acclaimed singer-songwriter and heartthrob, for the most sultry ballad on the Miseducation. The song represents a delusional kind of love, as the singers exchange verses of world-shattering catastrophes that seem insignificant compared to the intensity of love. Despite all the heartache Hill has expressed throughout the album, she’d still rather have loved and lost, and is willing to try again.
5. “Lost Ones”
On the “Intro” leading up to “Lost Ones,” Hill sets the scene as a classroom filled with students and a teacher deliberating over what it means to love. In a reworking of the routinely-sampled 1982 track “Bam Bam” by Sister Nancy, Hill comes out the gate with an eloquent boom-bap diss track, busting shots at all the naysayers, especially her ex-boyfriend and former bandmate: “My emancipation don’t fit your equation / I was on the humble, you on every station.” Breaking free from the Fugees caused understandable tension, even more so after a messy romantic breakup. It’s volatile and outright disrespectful, but plays like the initial anger in a difficult situation before setting pace for the beautiful breakthroughs in songs to come.
4. “To Zion” (feat. Carlos Santana)
Here, Hill addresses the other elephant in the room: a pregnancy at the height of her career, resulting in speculation about who the father might be. Although the timelines seem blurred, Wyclef Jean was married to someone other than Hill at the time and, unbeknownst to the public, Lauryn was romantically involved with Rohan Marley after recording much of Miseducation in Jamaica.
The song is led by Hill’s powerful vocals, over Carlos Santana’s mesmerizing guitar, as she celebrates her son despite the opinions of those telling her to focus on her musical career and the struggles of not being in a stable relationship.
Hill compares her pregnancy to the immaculate conception, symbolizing that, although she didn’t exactly plan for her son, she believes her son chose her and is a blessing from God.
This beautiful tribute to her first-born remains relevant today, at a time when women’s reproductive autonomy is being stripped from them — pressured by the men in her life to terminate her pregnancy for the sake of her career, Hill places her own desires above those of the money-making machine that surrounds her. She chooses for herself, and she chooses to keep her baby. For foresight, relevance and pulling on both heart strings and guitar strings, “Zion”rises to near the top of Miseducation.
3. “Can’t Take My Eyes Off of You (I Love You Baby)”
“Can’t Take My Eyes Off of You (I Love You Baby)” is technically another hidden bonus song (and a reimagining of a 1967 Frankie Valli song), but it deserves recognition as one of Miseducation‘s highlights. The song wasn’t released as a single, but began gaining radio play after appearing in the 1997 film Conspiracy Theory, eventually peaking at number two on Billboard’s Rhythmic chart.
Hill’s take on Valli’s hit record is a contender for remakes that outshine the originals. Try listening without cracking a smile — I dare you.
2. “Ex-Factor”
Hill has a knack for describing heartbreak with simplicity; it’s the reason the Miseducation remains timeless. In dealing with matters of the heart, regardless of the complexities found in different scenarios, both parties are fighting to be understood in a grey area that often becomes unnecessarily complicated: “It could all be so simple, but you’d rather make it hard,” she sings.
It samples Wu-Tang’s 1993 “Can It Be All So Simple,” which itself takes from Gladys Knight & the Pips’ cover of Barbra Streisand’s “The Way We Were.” It’s the song that keeps on giving, serving as a feel-good anthem for women everywhere, and it’s been sampled on loads of songs since including Drake’s “Nice For What” and Cardi B’s “Be Careful.”
“Ex-Factor” was the second single from the project, peaking at No. 21 on the Billboard Hot 100 and earning Hill the award for Best R&B/Soul Single by a female artist at the 2000 Soul Train Music Awards. Lest we forget, “Ex-Factor” might very well be the sole reason the term “reciprocity” is embedded in our vocabulary.
1. “Doo-Wop (That Thing)”
Hill is an equal opportunist; she comes for everyone equally, including herself, revealing the ills of modern relationships on a hip-hop song that nods to doo-wop, a genre popularized by African-Americans in the 1940s. “Doo Wop (That Thing)” was Hill’s first solo single, and it became her only song to reach number one on the US Billboard Hot 100.
On this track, humanity is called to do better, because no one can “win” if we are not “right within.” The women are put on game and alerted that, although patriarchy allows men to mistreat women, women can play into their own demise, making “that thing” a euphemism for both sex and money.
