Raised in South Orange, New Jersey, by a musical family, Lauryn Hill was destined to be a star from her childhood. At the age of thirteen she performed on It’s Showtime at the Apollo’s amateur night. In high school she founded the gospel choir and led the cheerleading team. At the age of seventeen she played the recurring role of Kira Johnson on the CBS soap opera As the World Turns. And when her senior year rolled around she costarred alongside Whoopi Goldberg in 1993’s Sister Act 2: Back in the Habit.
In high school Lauryn met Fugees member Pras and formed a trio called Tyme with him and a mutual friend. When the friend left the group, Pras’s cousin Wyclef Jean joined them and that’s how the Fugees came to be.
A year after Sister Act 2, the Fugees released their debut album, Blunted on Reality. It was nowhere near as big or successful as its follow-up, The Score, but that didn’t stop Rolling Stone (and other critics) from saying that “Hill, whose rich, sensuous alto is the Fugees’ most conspicuous selling point, should leave the guys behind and go solo.”
“I’d intended to be in the group forever, until I found myself in circumstances where I felt the inner desire to express myself, freely and openly without any constraint,” Hill said in a 2000 interview. “Without anybody saying ‘hey, you can’t say that! That’s not fly, you can’t say that’… The only way I could’ve done that was in doing a solo release.”
Here are some quick facts about that solo release, just so you can understand how BIG Miseducation was (and remains):
• Miseducation debuted at No. 1 the Billboard 200 chart—the first time a woman rapper had an album in that spot.
• The album was certified 3x platinum on November 4, 1998, just three months after it was released.
• The album’s first-week sales were the highest for a woman in any genre at the time.*
• Everyone fricking loved it. EW gave it an “A,” praising Lauryn’s ability to make an “album of often-astonishing power, strength, and feeling.” XXL said the album “not only verifies Lauryn Hill as the most exciting voice of a young, progressive hip-hop nation, it raises the standards for it.” Newsday called it “an ambitious, sprawling and superb recording.” I could keep going, but you get the gist.
• Artists from all genres of music have sung its praises—Maxwell, TLC, Kelly Rowland, Cyndi Lauper, and Jay-Z, who said with Miseducation Lauryn “made something that’s going to stand the test of time.”
• It was nominated for ten awards at the Grammys and Hill took home five golden gramophones: for Best R&B Album, Best R&B Song, Best Female R&B Vocal Performance, Best New Artist, and the big kahuna, Album of the Year. She was the first woman to win five awards at the ceremony and the first rapper to take home the coveted Album of the Year award.
Lauryn’s wins that night affirmed that hip-hop as a whole was award-worthy, but the fact that she also took home the most prestigious award in Album of the Year on top of it? That said her music, our music, was just as much of an art form as anyone else’s.
Now, I know you’re probably wondering, How did she win R&B awards while also being the first rapper to win the big award? And you wouldn’t be alone in that thought, because people have been debating whether or not Miseducation is a rap album or an R&B album since it dropped. Album cuts like “Ex-Factor,” “When It Hurts So Bad,” and “Nothing Even Matters” put Lauryn’s singing skills on full display and certainly fit the R&B bill. Then there’s the scathing diss track “Lost Ones” and the verses on “Doo Wop (That Thing)” that are most certainly rap.
The answer to your question is best answered by none other than Lauryn herself. In her 1998 cover story for The Source, Hill said, “I know this sounds crazy, but sometimes I treat rapping like singing, and other times I treat singing like rapping. But still, it’s all done within the context of hip-hop.” She’s a rapper, she’s a singer, the album is rap, the album is R&B, and it’s all hip-hop. Got it? Cool. Back to the Grammys.
Lauryn’s wins that night affirmed that hip-hop as a whole was award-worthy, but the fact that she also took home the most prestigious award in Album of the Year on top of it? That said her music, our music, was just as much of an art form as anyone else’s. Of course, we don’t need awards to tell us that, but the fact that Recording Academy members recognized Miseducation’s greatness makes me happy. It’s one of the times they got it “right.” With that in mind I always wondered, what if we as consumers could decide on the honors our favorite artists took home? Oftentimes an album or a song or an artist impacts listeners in ways that none of the categories can capture. And those specific points of impact best describe why a person wins—or should win—a Grammy in the first place!
So here are five more awards I would have given Ms. Lauryn Hill that night. All of them are totally made up. But all of them explain exactly why she won so many awards as well as Album of the Year.
Best Audible Middle Finger to Anyone Who Didn’t Support a Woman’s Right to Do Whatever She Wants: “To Zion”
When Cardi B revealed she was pregnant during her 2018 Saturday Night Live performance there were two groups of people: those who were ecstatic for Cardi and her journey into motherhood, and those who thought she was making a big mistake by having a baby at that point in her career. The response was exactly what Lauryn had heard a little over two decades earlier when people learned she was pregnant with her first child, Zion.
On “To Zion” Lauryn croons “‘Look at your career,’ they said / ‘Lauryn, baby use your head’ / But instead I chose to use my heart.” In this instance “they” represents the group of people who thought Lauryn was making a mistake by choosing to have a baby with her seminal solo album on the way. It wasn’t the “right time” or the “best circumstances,” to them.
But as Joan Morgan wrote her book She Begat This: 20 Years of The Miseducation of Lauryn Hill, “Black women rarely get credit for the strength it takes to choose motherhood in the face of both stigma and what the rest of society considers imperfect circumstances.”
In a society where men are the ones who decide what’s appropriate and what’s not, choosing “your way” instead of the “right way” directly goes against that idea. With “To Zion,” Lauryn affirmed your right to choose parenting on your terms. Why wouldn’t that be awarded?
Best Diss Song: “Lost Ones”
“It’s funny how money change a situation / Miscommunication leads to complication.” That’s how Ms. Lauryn Hill opens “Lost Ones,” the venomous track that’s widely believed to be a diss at Wyclef Jean. Not only were the two former groupmates, but Hill and Jean had dated for a period of time too. I don’t need to tell you that things didn’t necessarily end well.
The circumstances around how the song was initially released are part of what makes it so good. Joan Morgan tells the story in She Begat This, but I’m going to give you an abridged version.
Lauryn took “To Zion” to the then head of Sony Music and Entertainment, Tommy Mottola, and he was not feeling it. He wanted Lauryn’s music to sound like the Fugees, and as Morgan said he “thought this new mélange of soul, reggae, and relatively little hip hop from one of rap’s best emcees was too much of a departure from a proven formula.” That’s when Lauryn’s team decided to take “Lost Ones” to Ruffhouse Records so it could be pressed for distribution to DJs and mix shows. The song hit the streets like wildfire! And it made people want more Lauryn, thus creating the space for Miseducation to come through and blaze the charts.
So when she raps, “Who you gon’ scrimmage, like you the champion? / You might win some but you just lost one,” it’s a checkmate to Wyclef and Sony.
Best World Building on an Album: The Miseducation of Lauryn Hill
The thing that I love about the winner of that last award, “Lost Ones,” is that it interpolates Jamaican dance hall artist Sister Nancy’s “Bam Bam.” In 2016, Billboard said the song was “a strong contender for the title of most sampled reggae song of all time,” and listening to it once will explain why. It’s a smooth, bass-heavy riddim perfectly paired with Sister Nancy’s voice. It’s the perfect sample, especially when you remember that pioneers Cindy and Kool Herc are Jamaican, and that hip-hop and reggae have a close-knit relationship.
The thing that I love about the album is that, as Morgan said, Lauryn “deliberately wrote herself into the discourse of diaspora, drew on the global nature of black music, and fashioned herself a citizen of the world.”
When Lauryn invokes call-and-response patterns at the end of “To Zion,” it’s an element directly tied to the postslavery music that led to the formation of the blues. When Carlos Santana’s guitar starts playing at the opening of the same song, listeners are exposed to his influence by the blues and African rhythms. “Doo Wop (That Thing)” literally names the genre it’s inspired by, a kind of rhythm and blues born out of African American communities in the 1940s that relies on light instrumentation, ensemble singing, and group harmonies.
Lauryn and her collaborators incorporated the sounds of so many parts of the Black diaspora at every stop, and it sounds authentic, organic, and beautiful. Yes, she gets this award too.
Best Album Skits: The Miseducation of Lauryn Hill
I don’t know why there aren’t awards for album skits, but this is my petition to make it a reality. Miseducation opens by placing listeners in a classroom, the sound of a school bell signaling the start of class. Ras Baraka, an educator, author, and politician who would later become the mayor of Newark, starts taking attendance. When he gets to “Lauryn Hill,” he repeats her name a few times before it’s clear to the listener that she’s not in class.
The skits continue throughout the album, but my favorite one is placed right at the end of “To Zion,” when Baraka asks the class how many of them have ever been in love. The girls and boys in the room start sharing their definition of the word, and it’s an innocent, honest, and eye-opening conversation between children and an adult about the simplest thing we’ve ever complicated. “Willingness to do everything for that person,” says one boy. “Love is not phony!” says one of the girls. When asked how you know you’re in love, one of the girls says, “It’s sometimes, like when they try to act funny in front of they [sic] boys, like when they get around say [sic] they love you. They can’t love you. ’Cause love-love-love wouldn’t do that.”
The presence of the students on the album is storytelling at its finest, with the kids’ commentary rounding out a listening experience built around this idea of Lauryn’s “miseducation.” So yes, she gets this award too. And the kids should as well!
Most Prophetic Song: “The Miseducation of Lauryn Hill”
The last song on the original album release is so prophetic it’s not even funny. On the chorus Lauryn croons, “But deep in my heart, the answer, it was in me / And I made up my mind to define my own destiny.”
At the time that I’m writing this Miseducation remains Hill’s only studio album. She released her live album Unplugged No. 2.0 in 2002, and after that removed herself from the public. She’s dropped a few singles since then and appeared as a featured artist on a handful of songs. There have been shows here and there, and naturally a lot of calls from people for another album. Through it all Lauryn has stood firm in her desire to not let the music industry dictate her worth.
The legacy of Miseducation doesn’t exist without contention either. In 2001 Hill, her management team, and record label settled a lawsuit with a group of musicians who wanted songwriting and production on the album. As reported by Rolling Stone: “The four musicians claimed in the suit that they worked on arranging and producing all the cuts on Hill’s Grammy-winning solo debut, The Miseducation of Lauryn Hill, and requested partial writing credit on thirteen of the fourteen original tracks on the album, with percentages specified in the suit.”
The track they didn’t ask for credit on? “To Zion.”
The suit emphasizes the importance of proper credit, and also reminds me that an album isn’t any less impactful because of collaboration. In 2014 Miseducation was added to the Library of Congress’s National Recording Registry, which is an archive of recordings with cultural, aesthetic and historical significance, and in 2021 the album was certified diamond by the RIAA for selling ten million units, making her the first woman rapper to achieve this feat. The album still gets played because of its impact, and it won all of the Grammys it did because of its tremendous power. And if none of the categories she won even existed, the ones I proposed would do just fine.
Excerpted from FIRST THINGS FIRST: Hip-Hop Ladies Who Changed the Game © 2024 Nadirah Simmons and reprinted by permission from Twelve Books/Hachette Book Group.