Six-time Grammy award winner Lauryn Hill is widely regarded as one of the greatest female hip-hop and R&B artists ever. Her discography presents a wide range of excellent songs that speak to prevalent issues such as racism, over-sexualization in media, and women’s rights. When looking back at all the tracks Hill recorded, it is difficult to pinpoint just a few that stand out from the others; I’m convinced that she doesn’t have a single bad song. 

In this piece, I will attempt to compile the best works of Lauryn Hill in a 10-song playlist. In addition to her solo career, Hill was a member of the American hip-hop group the Fugees during the 1990s when the group created some of the most culturally significant music of the time. Given the difficulty of narrowing down Hill’s best music to just 10 songs, I made it a little easier for myself by restricting the songs to the one’s Hill has made as a solo artist or with a featured artist, and not those made with an organized group. 

Lost Ones

“Lost Ones” is easily a top-five song by Hill and a personal favorite of mine. From the album “The Miseducation of Lauryn Hill,” this song is a diss track directed at Hill’s old bandmate from the Fugees, Wyclef Jean. Hill and Jean had been in a relationship that ended sourly, so Hill uses this song as a way to get back at Jean and highlight all his faults. It showcases smooth rapping and powerful vocals brought to life by the fiery nature of the song. 

Why Does It Deserve A Spot?

Don’t just take it from me, listen to the critics. This song is a hip-hop masterpiece and the best of what the genre offers. It is ranked 45th on Rolling Stones’ ‘100 Greatest Hip-Hop Songs of All Time’ and is included on MTV’s ‘Rap’s Top 10 Diss Songs’ list. 

“Lost Ones” is a wonderful song to sing along to, because, although it is a diss song, it emits such a jovial mood. This song takes an intricate issue – a bad breakup – and simplifies it, making it easy for any listener to understand Hill’s conflict. If I had to choose one song to play for someone who had never listened to Hill before, this would surely be the one. 

Best Verse

“I was on the humble, you on every station 

Some want to play young Lauryn like she dumb 

But remember not a game new under the sun 

Everything you did has already been done”

In this verse, Hill is explaining the difference between her and Wyclef Jean, and how that created issues between them. She also states that there is nothing new under the sun, which is a biblical reference to Ecclesiastes 1:9, which says “What has been will be again, what has been done will be done again; there is nothing new under the sun.” This bit displays how aware Hill was of what was happening around her regarding the sometimes shady actions of her ex-boyfriend.

Doo-Wop (That Thing)

Next up is a classic, “Doo-Wop.” Any listing of Hill’s best songs would be incomplete without this piece. “Doo-Wop” is arguably the most popular song from “The Miseducation of Lauryn Hill” and it is showered with accolades. From its debut, it was number one in the United States on Billboard’s Hot 100. It won big at the 1999 Grammys, earning the award for Best R&B Song and Best Female R&B Vocal Performance. It was also placed on the Rolling Stones 500 Greatest Songs of All Time list, coming in at 49th. The list of achievements and awards runs on, and rightfully so.

Why Does it Deserve a Spot?

“Doo-Wop” was and still is culturally significant because it speaks to issues like being exploited by the opposite gender, knowing your self-worth, and being a person of integrity in relationships. One thing I love about Hill is her ability to take serious topics and perform them in such a laid-back way while still respecting the subject. That’s a difficult thing to do, but she does it time and time again, and the best example of that is “Doo-Wop.”

Not only is this song full of life lessons and breakdowns of societal problems, but it also features some of Hill’s best vocals. Once again combining rapping and vocals, Hill did what she does best and left audiences speechless as she effortlessly jumped from verse to verse. 

If you need encouragement or wisdom, “Doo-Wop” is the perfect song.

Best Verse

“Girlfriend, let me break it down for you again

You know I only say it ’cause I’m truly genuine

Don’t be a hard rock when you really are a gem

Baby girl, respect is just a minimum”

Early in the song, Hill comes out swinging with heavy-hitting lyrics. She states her message clearly: know your self-worth and live up to it. I love this song because of verses like this where Hill is speaking from her heart and giving honest advice. It takes the music to another level and forces you to slow down and think about what is being said. 

I Gotta Find Peace of Mind 

“I Gotta Find Peace of Mind” is a song from a fairly unknown work of Hill’s. In 2001, Hill recorded a live album for MTV Unplugged in which she played the guitar and performed 22 original songs. This album didn’t come close to the levels of recognition “Miseducation” received, but it is notable in its own right, garnering attention for its sound messages about love, power, and faith. 

The key message in “I Gotta Find Peace of Mind” revolves around Hill finding herself, reaffirming her faith in God, and trying to make sense of the romantic relationships she’s held past and present. Differing from the previous songs on this list, “I Gotta Find Peace of Mind” could be categorized as soul and folk music, taking a step away from what we typically hear from Hill.

Why Does it Deserve a Spot?

“I Gotta Find Peace of Mind” delves into a more personal side of Hill and exposes her exceptional talent as a songwriter. In Hill’s other more popular songs, she touches on some heavier topics, but she doesn’t go as in-depth or personal as she does with this song. That is likely because this song is part of the MTV Unplugged series, where artists have a live audience but are still in a very intimate and exploratory setting. “I Gotta Find Peace of Mind” perfectly balances out any Hill playlist because it displays how well-rounded Hill is as an artist. 

Best Verse

“You love me despite myself

Sometimes I, I fight myself

I just can’t believe that you, would have anything to do

With someone so insecure, someone so immature

Oh you inspire me, to be the higher me”

Throughout the song, Hill makes several religious connections, but in this verse specifically, she is singing to God and questioning why he continues loving her with all her flaws. This verse perfectly displays how personal and vulnerable Hill gets in “I Gotta Find Peace of Mind”. 

Can’t Take My Eyes Off You

“Can’t Take My Eyes Off You” was a hit during the 1990s and has stood the test of time, still holding up as an extremely popular R&B single. This is the first song on this list that is a love song, and it is beautiful. Hill’s dynamic vocal range really shines through in “Can’t Take My Eyes Off You” and makes this song an incredibly easy listen. 

Why Does it Deserve a Spot?

Every playlist needs a fun and lighthearted song, and that’s where “Can’t Take My Eyes Off You” comes in. Not only does it balance out the deeper and more emotional songs on the playlist, but it’s also an easy song to sing and relate to. No matter your relationship status, you can likely resonate with the feelings of being in love that Hill is singing about. 

And if that hasn’t drawn you in yet, “Can’t Take My Eyes Off You” is a very catchy song; but not in a bothersome way. It’s the kind of song that sticks with you because of its easy going vibe and superior vocals.

Best Verse

“At long last, love has arrived

And I thank God I’m alive

You’re just too good to be true

Can’t take my eyes off you”

Continuing with a partially religious theme, Hill proclaims deep love and appreciation for her significant other. One defining feature that sets Hill apart from many artists of today’s time is her ability to write love songs without being lustful or excessively raunchy. She expresses pure love in a passionately poetic manner that makes “Can’t Take My Eyes Off You” a memorable and charming love song.

Ex-Factor

One thing Hill does well is diss tracks, and this list features another, tempestuous piece aimed at her former bandmate, Wyclef Jean. With “Ex-Factor,” Hill climbed the charts once again, reaching as high as number 21 on the U.S. Billboard Hot 100 and peaking at number seven on the US Hot R&B/Hip-Hop Songs. 

Not only has “Ex-Factor” earned numerous accolades and well-deserved attention, but it has also achieved the highest form of flattery, imitation. With prominent artists like Drake, Cardi B, and Kehlani sampling “Ex-Factor,”Hill has made a deep-rooted impact on R&B and Hip Hop. 

Why Does it Deserve a Spot?

I would be remiss to leave “Ex-Factor” off this list, and I can’t imagine a Hill jam session without this song. With extensive cultural influence and exceptional vocal performance, “Ex-Factor’ is an impressive display of Hill’s talents. Taking credit for both writing and producing this song, Hill shows the world why she is one of R&B and Hip Hop’s greatest female artists. 

Hill writes with such emotional vigor without appearing unhinged or unruly. In four minutes and thirty-seven seconds, Hill dissects the complex issue of infidelity and emotional abuse. “Ex-Factor” is a song that you have to hear for yourself to truly understand, so take a listen. 

Best Verse

“Loving you is like a battle (it’s like a battle)

And we both end up with scars

Tell me, who I have to be (who I have to be)

To get some reciprocity”

In “Ex-Factor,” Hill litters her lyrics with allusions to a rocky and immoral relationship that ultimately results in her being emotionally damaged. In this verse, she compares her relationship to a battle that leaves both parties hurt and questions what more she has to do to get mutual respect from her significant other. 

Freedom Time

Switching back to Hill’s MTV Unplugged album, “Freedom Time” is a track that highlights her intriguing views on society and religion. In this song, Hill focuses heavily on the idea of being a slave to your mind and being misguided by evil forces present in society such as lust. If you are looking for a song that is intellectual, thought-provoking, and musically sound, “Freedom Time” is the perfect fit. 

Why Does it Deserve a Spot?

“Freedom Time” reveals the immense range Hill has: not only can she deliver a solid love song or diss track, but she can also successfully craft a serious song that may be deemed controversial. While “Freedom Time” is heavy on the lyrics and underlying messages, it doesn’t fall short with the musicality. As with all the pieces Hill creates, this song advertises Hill’s soulful vocals and renowned rapping skills. 

Best Verse

“His word has nailed

Everything to the tree

Severing all of me

From all that I used to be”

It was a tall task to single out one verse from “Freedom Time” but I felt this verse encapsulates the key message of the song. It touches on the belief that Jesus Christ was nailed to the cross and died for our sins. Hill then makes a personal connection, stating that Christ’s sacrifice made her a new person, with no ties to her old self. 

I like this verse because it unveils how personal the MTV Unplugged album, and specifically this song, was for Hill. She delved into her personal convictions and what was holding her back from being the best version of herself.

If I Ruled The World

“If I Ruled The World” is the first song on this list where Hill is a featured artist, and in this song, she works with rapper Nas to create a Hip Hop masterpiece. I love this song because of its smooth style and liveliness, and how well Nas and Hill’s voices mesh together.

Nas and Hill put their creative minds together, and the result was a critically acclaimed piece that sent Hill soaring into the spotlight. “If I Ruled The World” peaked at number 20 on the Hot R&B/Hip-Hop Singles & Tracks chart and was nominated for a Grammy in 1997 for Best Rap Solo Performance. Not only did it reach national fame from its debut, it was certified Platinum in June 2021 by the Recording Industry Association of America. 

Why Does it Deserve a Spot?

In the hip hop community, Nas and Hill are highly respected artists, so for them to collaborate on a song was like the meeting of two geniuses. I can’t get over how smoothly this song flows, and I hum the main chorus throughout my day.

If you haven’t listened to “If I Ruled The World” yet, don’t wait. It’s a staple piece of music and a wonderful introduction into the musical genius of both Nas and Hill. 

Best Verse

“If I ruled the world and everything in it, sky’s the limit

I push a Q-45 Infiniti

It wouldn’t be no such thing as jealousies, or B Felony

Strictly living longevity to the destiny”

This verse is really powerful because it spells out the world Nas wants to live in, and how much more peaceful and prosperous it would be than the current one. The entire song is based around the idea that if Nas and Hill “ruled the world,” there’s a long list of things they would like to change. This verse lays out specific things Nas would do or have; one being a nicer car, and two a world in which violent crimes — classified as B felonies — would no longer occur. 

To Zion

If I had to select a song that defined Hill’s religious roots, “To Zion” would surely be the one. It is a beautiful testament of Hill’s profound love for her first child and son, Zion David, as well as a proclamation of her faith in God. This song is easily the most emotional song from “The Miseducation of Lauryn Hill” and it gives us a glimpse of Hill’s journey as a young mother.

“To Zion” didn’t receive the attention or fame that songs like “Lost Ones” and “Can’t Take My Eyes Off You” did, but it made a name for itself as a deeply personal and vulnerable piece. 

Why Does it Deserve a Spot?

“To Zion” balances out nicely with the diss tracks and love songs on this playlist. It has a strong religious theme, and it shows another side of Hill that can sometimes be overshadowed in her other songs. In a similar fashion to all the pieces Hill makes, she serenades listeners with a raspy and soulful tone. 

Best Verse

“To come through unto life to be

A beautiful reflection of his grace

See I know that a gift so great

Is only one God could create

And I’m reminded every time I see your face”

I love this verse because it is so well written and Hill’s vocals are amazing. Hill also explains the love she has for her child in a deeply poetic and religious manner. This verse embodies the main message of the song and sums up how Hill ties her motherhood into her faith.

Every Ghetto, Every City

Essentially an autobiography, in “Every Ghetto, Every City” Hill takes the listener on a journey through her early life in South Orange, New Jersey using vivid recollections that paint a dynamic view of her childhood. This is a really upbeat piece that has many similarities to the neo-soul and funk style of Stevie Wonder. Once again combining rap and vocals, Hill draws in listeners with a laid-back tone and poetic lyrics.

I consider “Every Ghetto, Every City” to be an extremely underrated and overlooked song from the “Miseducation” album. Hill isn’t philosophizing about the world and all its problems or dissing former bandmates as she does in her other songs, so “Every Ghetto, Every City” gets neglected. I enjoy this piece because it has a sort of nostalgic feeling to it, and although I can not relate to any of the experiences Hill draws from, I still feel as if I am right there with her on those New Jersey streets.

Why Does it Deserve a Spot?

If you’ve ever been curious about what made Hill into the superstar she is today, “Every Ghetto, Every City” is the perfect answer to your questions. Hill takes a deeply layered and personal topic, and lays it out simply. She highlights the best parts of her childhood, then sharply contrasts the moments that almost kept her from achieving her dreams. In my eyes, “Every Ghetto, Every City” is a flawless song, and one of the best pieces from the “Miseducation” album.

Not to be forgotten, the musicality of “Every Ghetto, Every City” is stellar. Nothing short of a revolutionary, Hill broke barriers in the music industry by introducing the fusion of rap and soul with “Every Ghetto, Every City”. Once again, Hill draws sharp parallels to Stevie Wonder with the neo-soul sound she produces.

Best Verse

“My mother always thought I’d be a star

But way before the record deals

Streets that nurtured Lauryn Hill

Made sure that I’d never go too far”

While this is not the most insightful or interesting verse from the song, I find it to be the most important. It introduces the main idea of the piece and paints Hill’s journey as one from humble beginnings. The clever language in this verse is a theme that carries throughout the song, and makes “Every Ghetto, Every City” one of my favorite songs. 

His Eye Is On The Sparrow

Wrapping up this list, we have “His Eye Is On The Sparrow” which fans of the movie, “Sister Act II: Back In The Habit” will recognize. This film gave Hill her acting break, shooting her into national stardom for not only her on screen skills but also her amazing voice. 

In “Sister Act II: Back In The Habit”, Hill sings a short piece of the gospel song, “His Eye Is On The Sparrow”, which garnered calls for Hill to perform the full song. Giving the fans what they wanted, Hill partnered with costar Tanya Blount to record a full version of the song which was released in 1993. Hill and Blount’s voices blend effortlessly and they hit every note with ease. 

Why Does it Deserve a Spot?

While most Hill fans aren’t familiar with “His Eye Is On The Sparrow” or the Sister Act II movie, this song is a noteworthy gem. Stepping outside of her usual sound with a gospel piece, Hill performs this song angelically. With soulful vocals and the partnership with Blount, Hill delivers an amazing piece and leaves the audience satisfied. 

Best Verse

“I sing because I’m happy

I sing because I’m free

His eye is on the sparrow

And I know He watches me (He watches me)”

This verse is a reference to Matthew 10:29-31, which says “Are not two sparrows sold for a penny? Yet not one of them will fall to the ground outside your Father’s care. And even the very hairs of your head are all numbered. So don’t be afraid; you are worth more than many sparrows.” 

Using this background knowledge, it’s easy to understand that the song is explaining just how much God values each and every one of his creations. The song is explaining that despite how lonely life can feel, it is comforting to know that God is watching over you. I really like this verse because it is joyful and particularly uplifting.

Conclusion 

Hill boasts a discography full of a diverse range of songs, so it was no easy task to pick out the best of the best. After much research — which mostly meant spending hours listening to her music — I finally decided on the tracks that I thought best represented Hill and showcased her insane musical talent. 

These ten songs are pieces that I really enjoy listening to and analyzing, and I hope that you will too.