In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
I couldn’t stop looking at the clock. My eyes jut kept gravitating to those blinking red numbers. Four years ago, I was in a park in Chicago, watching Ms. Lauryn Hill close out the Pitchfork Music Festival. It had been a gamble to book Lauryn Hill. L-Boogie was on tour to celebrate the 20th anniversary of The Miseducation Of Lauryn Hill, the only solo studio album that she has ever released in her entire life. The idea was that Ms. Lauryn would perform every song from the album every night, but previous nights on that tour had not gone so well. Hill was and is notorious for coming to the stage late, and some of those shows had to be shut down before she finished her set. In Chicago, someone had installed a digital countdown clock on the side of the stage. It was out of view for most of the audience, but I was standing in a fenced-off journalists’ area by the side of the stage, and I could just not look away from that clock.
That night, the Lauryn Hill live-show experience was strange but vivid. Miseducation is a near-perfect album, a universally beloved artifact from the end of the monoculture age. It had won just about every commercial and critical plaudit that an album could possibly win. Onstage, though, Hill and her band radically rearranged the songs, to the point where they were nearly unrecognizable. When songs would start to wind down, Hill would gesture for her band to keep awkwardly vamping. In my little area of the crowd, an anxious hum got louder and louder. Hill only had a few minutes of stage time left, and she hadn’t played any of her biggest hits. What would happen when that clock hit zero? The Pitchfork Fest was in a public park, and it had to end at a certain point.
Lauryn Hill was not worried about the clock. When it hit zero, someone hit some kind of snooze button, and 10 more minutes magically appeared. When those 10 minutes ran out, another 10 appeared. When those 10 minutes ran out, the clock just blinked zero, and Lauryn Hill paid it no mind whatsover. She just kept performing until she finally closed things out with the only #1 pop hit of her career. Here’s how I put it when I wrote about the performance: “Lauryn Hill played chicken with the entire concept of time, and she won.”
Lauryn Hill, you see, does not particularly care for other people’s deadlines. Over the years, she’s made that very clear. The whole arc of Hill’s career has been messy and confounding. She’s generally remembered as one of the greatest rappers and singers of an era when singers didn’t really rap and rappers didn’t really sing. She left behind a hugely successful group and made an even-more-successful solo album, and then she just disappeared. When she has resurfaced in the years since, she’s done it entirely according to her own terms, and she has frustrated a great many people in the process. But Hill doesn’t care about that, and she probably shouldn’t care about that. She made The Miseducation Of Lauryn Hill, and that has earned her the right to ignore other people’s advice. So it’s funny that Hill’s biggest hit, her only chart-topper, consists entirely of her giving advice to other people.
You can see Lauryn Hill’s defiant streak in some of the oldest footage of her performing in front of audiences. Hill was born in Newark, and she grew up in a middle-class family in suburban South Orange, New Jersey. (When Hill was born, the #1 song in America was Earth, Wind & Fire’s “Shining Star,” which feels appropriate.) Hill’s parents were amateur musicians, and when Hill was a kid, she fell in love with her mother’s stack of old soul records. Young Lauryn Hill loved performing, and in 1988, when she was 13, she got booked to sing at one of the amateur-night showcases on Showtime At The Apollo. It didn’t go well, until it did.
The Showtime At The Apollo audiences were notoriously vicious, and their impatience with performers was one of the show’s big selling points, but it’s still pretty shocking to see how that crowd treated a 13-year-old kid on that night in 1988. Hill sang “Who’s Lovin’ You,” the 1960 single that Smokey Robinson wrote for his group, former Number Ones artists the Miracles. (The Miracles’ “Who’s Lovin’ You” never charted, but Brenda And The Tabulations’ 1967 cover peaked at #66.) At the beginning of the song, Hill’s voice wobbled nervously for a split-second, and the crowd just immediately turned on her, practically booing her out of the building. But Hill never reacted, and the Sandman never came out with his stage-hook. She just kept singing, growing more confident as she kept going. By the time she finished, she’d audibly won over a large portion of the crowd. The video of that performance would seem hacky if it was a movie scene. But it wasn’t a movie scene. It was real. After that, how could Lauryn Hill ever worry about a blinking countdown clock on the side of a stage?
In high school, Lauryn Hill was a straight-A student, but academics weren’t her only focus. In ninth grade, Hill teamed up with classmate Pras Michel to form a rap group called the Translator Crew. Eventually, Pras’ cousin Wyclef joined the group, and the Translator Crew became the Fugees. At first, Hill sang the choruses, but then she learned to rap. Pretty soon, she was rapping better than the two guys in her group.
For a while, the Fugees were strictly a leisure-time activity for Lauryn Hill. Before she finished high school, she already had the beginnings of a hugely promising acting career. In 1991, she was MC Lyte’s understudy in Club XII, a rap-themed Off-Broadway production of Shakespeare’s Twelfth Night. (Wyclef was in the play, too.) Soon afterwards, Hill landed a role on the soap opera As The World Turns. In 1993, an 18-year-old Lauryn Hill made her big-screen debut in Sister Act 2: Back In The Habit. Her musical numbers were pretty clearly the best thing about the movie, and she immediately looked like a star.
That same year, Hill also graduated from high school and played a small role in Steven Soderbergh’s King Of The Hill, and the Fugees signed with Columbia’s Ruffhouse imprint. She and Wyclef Jean, who was six years older and married, became an on-and-off couple. The Fugees’ 1994 debut album Blunted On Reality was hugely promising, full of dancehall overtones and acoustic guitars, but it was also a bit messy and disjointed. Blunted On Reality wasn’t a hit, but the single “Nappy Heads” crossed over and reached #49. On that song, Hill fit nicely with her two compadres, but she also seemed so much more effortless than either of them. While all of this was happening, Hill also went into her freshman year at Columbia University.
Hill stayed at Columbia even after the Fugees blew up. The trio’s 1996 sophomore album The Score improved on Blunted On Reality in every conceivable way. There’s some stuff on the album that doesn’t quite work; I always thought Wyclef’s acoustic-guitar cover of Bob Marley’s “No Woman No Cry” was dorm-room hokum. But the vast majority of The Score is pure gold. All three rappers were tougher and more confident, and they’d made tracks that gave them space to operate. All through The Score, Lauryn Hill is on fire, both as a rapper and a singer. Her hook on lead single “Fu-Gee-La” just floats.
“Fu-Gee-La” peaked at #29 on the Hot 100, and it remains the Fugees’ highest-charting single, but that doesn’t tell you anything about that album’s impact. The Score was a full-on rap blockbuster, topping the Billboard album chart and eventually selling seven million copies in the US alone. The real big hit on The Score didn’t have any rapping at all. Instead, the album took off on the strength of the group’s cover of Roberta Flack’s “Killing Me Softly With His Song.” Wyclef had some ad-libs on the track, but it’s almost entirely a solo showcase for Lauryn Hill, who wails the song out evocatively over A Tribe Called Quest and Rotary Connection samples. I like her version better than the Flack original.
The Fugees’ “Killing Me Softly” never came out as a commercial single, so it never charted on the Hot 100, but it was one of 1996’s defining summer jams. Even after what Hill did with that song, though, Wyclef Jean clearly believed himself to be the leader of the Fugees. At live shows, he’d hog the spotlight, doing backflips or playing guitar behind his head. One of Hill’s big moments that year didn’t have anything to do with the Fugees; it came when she sang the hook on Nas’ single “If I Ruled The World (Imagine That),” which peaked at #53.
The year after The Score, Wyclef became the first Fugee to go solo. Clef’s 1997 solo album The Carnival went double platinum, and he made it to #7 with his weirdly beautiful orchestral folk-rap experiment “Gone Till November.” (It’s a 10, and it’s still Wyclef’s highest-charting single as lead artist. As a guest-rapper and a producer, Wyclef will eventually appear in this column.) Lauryn appeared on a few tracks from The Carnival, but she wouldn’t work with Wyclef again for years afterward.
Before Lauryn Hill and Wyclef broke up for good, Hill met Bob Marley’s son Rohan, who was playing football for the University Of Miami, and she got pregnant. Marley and Hill’s son Zion was born in 1997, shortly after Hill dropped out of Columbia and turned 20. Hill deeply resented everyone who told her that motherhood would be bad for her career, and she also resented everyone at her label who wanted more Fugees music when she wanted to go solo.
Hill didn’t just want to make a solo album; she wanted to write and produce the whole thing herself. She got her way. While she was pregnant, Hill wrote and produced songs for legends like CeCe Winans, Whitney Houston, and Aretha Franklin. (Aretha’s Hill-produced 1998 single “A Rose Is Still A Rose” peaked at #28.) Around the same time, Hill assembled a group of New Jersey musicians that she called New Ark, and they got started recording The Miseducation Of Lauryn Hill in New York and Jamaica.
The Miseducation Of Lauryn Hill is one of those rare popular-music miracles. Hill and her collaborators figured out a seamless blend of samples and live instrumentation, and Hill herself slid back and forth between singing and rapping almost effortlessly. (There’s still a debate over whether Miseducation should be considered a rap album or an R&B album. It’s both, obviously, though I was bummed out at the time that Hill didn’t do more rapping on the record.) On the album, Hill took aim at Wyclef, without specifying who she was going after, and she also vented rage at everyone who’d questioned her decision to become a mother. But Miseducation isn’t an angry album. It’s a whole universe of a record, one that’s full of love and joy and heartbreak and nostalgia and glowing pride. The album was often grouped within the neo-soul movement that was picking up steam around that moment, and Hill did work with a few neo-soul standouts like D’Angelo and keyboardist James Poyser. But it’s pretty clearly just a Lauryn Hill record — the Lauryn Hill record — and it exists outside the context of just about everything else that was happening in pop at the time.
Miseducation was an immediate critical and commercial smash. It drew rapturous reviews from just about every publication, and it debuted at #1, selling nearly a half-million copies in its first week. For a while, nearly a half-dozen Miseducation tracks were in radio rotation; I damn near crashed my parents’ minivan the first time I heard “Lost Ones” on 92Q. But the song that got the biggest push was “Doo Wop (That Thing),” which might honestly be my least favorite song on the album
It’s easy enough to see why “Doo Wop (That Thing)” was the single. It’s a bright, peppy, joyous track, and it features Hill both singing and rapping about as well as anyone can sing or rap. Hill used a sped-up sample of “Together Let’s Find Love,” a song that former Number Ones artists the Fifth Dimension released in 1972. (“Together Let’s Find Love” peaked at #37.) The sample was only part of the “Doo Wop (That Thing)” track. James Poyser, a prolific collaborator who’s now a full-time member of the Roots, added a prim, icy piano line. Hill’s collaborators jumped in with jubilant horn-stabs, DJ scratches, and a Motown-style string arrangement that really hits hard on the bridge.
Lauryn Hill’s multi-tracked vocals are all over “Doo Wop (That Thing).” Her sung chorus is worded as a warning — “girls, you know you better watch out” — but Hill sings it like she’s celebrating. That’s the tension of “Doo Wop.” It sounds like a party song, even if the lyrics are manifestly preachy. On the second verse, Hill admonishes a strawman who’s “more concerned with his rims and his Timbs than his women.” It’s all a little pat, but if she’s pissed at guys who skip out on fatherhood and dodge child support payments, that’s fair game. It’s the first verse that gives me pause.
The first verse of “Doo Wop (That Thing)” is one big finger-wag at young women who are showing off ass because they think that it’s a trend or selling their souls because it’s in. Hill tries to relate to these young women — “Now, Lauryn is only human/ Don’t think I haven’t been through the same predicament” — but she still talks down to them, and not always in a big-sisterly way. In fact, she literally preaches: “That was the sin that did Jezebel in/ Who you gon’ tell when the repercussions spin?” Maybe this is hypocritical, but that kind of respectability-politics rap — huge among the left-of-center crowd at the time — grates on me way more than the hedonistic stuff. At the end of the verse, Hill veers perilously close to judgmental-asshole territory: “Look at where you be in/ Hair weaves like Europeans/ Fake nails done by Koreans/ Come again.”
In a Details interview at the time, Lauryn Hill didn’t quite disavow the suggestion that she was going after rap peers like Lil Kim, someone who will eventually appear in this column: “I’m not dissing them; I’m dissing their mindset. My music talks about a certain way of thinking, and if the cap fits, you know? I knew girls like Kim growing up — I might have even been one at a certain age — and there’s a huge lack of self-esteem behind that thinking.” With the benefit of hindsight, I would dispute the notion that Lil Kim ever lacked for self-esteem.
That kind of hectoring viewpoint always bugged me, and maybe that’s a me thing. (My parents were big on hectoring.) It doesn’t stop “Doo Wop (That Thing)” from being a truly great song, but it’s never sat quite right with me. On the other hand, maybe those lyrics are one side of a conversation that was happening within the black community, and maybe it doesn’t matter what I think of them. (I mean, it definitely doesn’t matter what I think of those lyrics. It doesn’t matter what I think of any of the songs that appear in this column. Who the fuck am I?)
For the “Doo Wop” video, Lauryn Hill pulled off a neat trick. The British directing duo known as Big TV staged a sort of time-traveling block party. In splitscreen, we see two different Lauryn Hills at two different neighborhood jams on the same Washington Heights block — one in 1967, one in 1998. The old-timey Lauryn sings; the then-contemporary one raps. (It’s a little sobering to realize that we’re almost far-removed enough from 1998 that you could practically recreate that video today, with 1998 Lauryn as the relic of the past.) The concept is a little cutesy, and the imagery has that weird late-’90s Gap-commercial sheen to it, but Lauryn makes it work through sheer charisma and precision. That bit where the two different Lauryns do the same shimmy-sway move in unison? Cinematic magic, baby.
At first, “Doo Wop (That Thing)” wasn’t going to come out as a commercial single. But Miseducation was an overwhelming success, so Columbia printed up a limited number of “Doo Wop” singles and released them in October 1998. The album had been out for two months, and it was already double platinum. The “Doo Wop” single debuted at #1, and it became Hill’s only top-10 hit.
Two other singles from Miseducation charted — “Ex-Factor” at #21, “Everything Is Everything” at #35. But Miseducation was intended to function as a full album, and that’s what it did. In 1999, it became the first rap-identified record to win Album Of The Year at the Grammys. In the 23 years since then, only one rap-adjacent record has won that award. (Five years later, OutKast, Lauryn Hill’s opening act on the Miseducation tour, took Album Of The Year home. They’ll appear in this column eventually.) Miseducation kept selling, and it finally went diamond last year.
Soon after the release of Miseducation, the New Ark musicians who’d played on the album sued Lauryn Hill. Possibly at the behest of her label, Hill had been credited as the sole songwriter and producer of every song on the album. The musicians argued that they’d had a hand in writing many of the songs, and they wanted their credit. Hill settled that lawsuit out of court in 2001. The lawsuit, combined with the overwhelming levels of fame that came with the album’s success, had a huge effect on Hill. She still hasn’t released a follow-up album. The closest thing arrived in 2002, when Hill released her live double album MTV Unplugged No. 2.0. Hill had taped her entire Unplugged special without accompaniment, singing and rapping and playing acoustic guitar all on her own. The songs were entirely new, and the whole thing seemed baffling. The most emblematic song might be “I Gotta Find Peace Of Mind,” which is nine minutes long and which ends with Hill breaking down in tears.
Unplugged was a bold statement, and it has fans, but I’ve hardly ever returned to the record. It still went platinum, but that was far cry from what Hill had done with Miseducation three years earlier. Hill was already isolating herself from the public before Unplugged. She kept up her off-and-on relationship with Rohan Marley, and she now has six kids, five of them with Marley. (In 2017, 19-year-old Zion became a father, and 42-year-old Lauryn Hill became a grandmother.) Hill fell in with a vaguely shady spiritual advisor who some concerned observers likened to a cult leader. She also served a few months in prison for tax evasion in 2013.
In the last two decades, Lauryn Hill’s career has been an inconsistent thing. She reunited with the Fugees for the concert film Dave Chappelle’s Block Party in 2004. The Fugees also played the BET Awards and released a forgettable reunion single, but then they went their separate ways again. Hill popped up with random songs that didn’t leave much of an impression — one for a Passion Of The Christ companion-piece album in 2004, another for the penguin cartoon movie Surf’s Up in 2007. None of it seems to make much sense.
Lauryn Hill has done a lot of touring in recent years, though everyone who goes to see her has to understand that the show may or may not happen as planned. Last year, for instance, the Fugees announced a whole arena-level reunion tour, but then they called the whole thing off after doing one warm-up show in New York. Hill seems to be recording more and more lately. Last year, for instance, she had two songs out in the world — one track on the soundtrack of the Netflix western The Harder They Fall and one honestly-impressive guest-verse on a Nas track.
I continue to hold out hope that Lauryn Hill will one day return triumphant — that she’ll make another masterpiece and that the public will greet her with the same awe that we rightly gave her when she made Miseducation. Maybe it’ll happen. Maybe we’ll see Lauryn Hill in this column again. Maybe not. (Lauryn Hill, in sampled form, will definitely reappear in the column.) If Lauryn Hill ever does come back, she won’t do it on anyone else’s schedule. But if Miseducation is the first and last real solo statement from Lauryn Hill, then that’s a pretty amazing legacy, too.
BONUS BEATS: Here’s Madlib and his Quasimoto alter-ego rapping over a chopped-up “Doo Wop (That Thing)” sample on the 2002 track “LAX To JFK”:
BONUS BONUS BEATS: Here’s the late Amy Winehouse singing a medley of “Doo Wop (That Thing)” and her own song “He Can Only Hold Her” at a 2007 live show:
(Amy Winehouse’s highest-charting single, 2007’s “Rehab,” peaked at #9. It’s a 9.)
BONUS BONUS BONUS BEATS: Here’s some relatively crude footage of Rihanna covering “Doo Wop (That Thing)” while opening Kanye West’s Glow In The Dark tour in 2008:
(Rihanna will eventually appear in this column a bunch of times.)
BONUS BONUS BONUS BEATS: Here’s Drake rapping over a “Doo Wop (That Thing)” sample on his 2019 loosie “Draft Day”:
(Drake will appear in this column a great many times, and one of his future appearances will feature a different Lauryn Hill sample.)
BONUS BONUS BONUS BONUS BEATS: Kanye West tried to sample Lauryn Hill’s Unplugged track “Mystery Of Iniquity” on his 2004 single “All Falls Down,” but he couldn’t get the sample cleared. Instead, he got Syleena Johnson to sing that bit from Hill’s song, and Hill got a co-writer credit. (“All Falls Down” peaked at #7. It’s an 8.) Kanye did, however, manage to sample “Doo Wop (That Thing)” on his 2021 track “Believe What I Say.” Here it is:
(“Believe What I Say” peaked at #28. Kanye West will eventually appear in this column.)
The Number Ones: Twenty Chart-Topping Hits That Reveal The History Of Pop Music is out 11/15 via Hachette Books. You can pre-order it here.