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.
It’s one of the great foundational questions in pop music: To get down or not to get down? Through much of its lifetime, pop music has been one of the few art forms that aims for mass audiences while still taking matters of teenage sexuality seriously. Sex is a loaded subject for just about anyone, but it’s especially loaded for teenagers, whose hormones are constantly out of control and who are continually besieged by contradictory messages about what they’re supposed to do with those hormones. Questions about sex were central to pop music even when the songs had to hide the implications of those questions. Those are the questions that the Shirelles, teenagers themselves, asked on “Will You Love Me Tomorrow” in 1961. Nearly 40 years later, another teenage pop star asked those same questions on another #1 hit. She just phrased them differently.
Monica Denise Arnold sounded like a grown-ass R&B singer when she first emerged with the 1995 single “Don’t Take It Personal (One Of Dem Days),” a song that’s all about needing to spend some time alone even when you’re in a relationship. That’s a mature sentiment, and Monica sang in a controlled and full-bodied gospel-derived rasp. But Monica was a little kid. “Don’t Take It Personal” peaked at #2 when Monica was 14, and she recorded it when she was even younger. (It’s an 8.) On her follow-up single “Like This And Like That,” Monica threatened to leave someone who wouldn’t properly commit, another grown-up concern. (That one peaked at #7. It’s another 8.)
I’m about the same age as Monica, but I don’t remember ever thinking of her as a kid, or even as a peer. She seemed to have the same impeccable cool as the R&B singers who were a generation older. Monica’s 1995 debut album was called Miss Thang, but she never embodied the precocity that the phrase implied. Instead, she seemed to arrive fully formed. So there was something striking about the way that parts of Monica’s second album used that arch, poised, muscular voice to address the sorts of questions that might keep an actual kid awake at night.
When Monica’s sophomore album arrived in stores, she was already sitting on top of the Hot 100. Monica’s peer Brandy had invited her to sing on “The Boy Is Mine,” and that song conquered the pop charts for the entire summer of 1998. At the behest of her label boss Clive Davis, Monica used The Boy Is Mine as her album title, and she released that album just a month after Brandy released her own sophomore album Never Say Never. Brandy was reportedly mightily pissed at Monica’s album title, and it probably helped fuel the ongoing beef that became a big subplot in both singers’ public lives.
Where Never Say Never is a relatively cohesive album, mostly recorded with Brandy’s new collaborator Rodney “Darkchild” Jerkins, The Boy Is Mine has Clive Davis’ fingerprints all over it, and it’s all over the place when compared to Brandy’s record. Monica’s mentor Dallas Austin had signed her to his Rowdy imprint, and he and his proteges had produced most of Miss Thang. But before she released The Boy Is Mine, Monica moved over from Rowdy to the main Arista label. Clive Davis, still working from the playbook that he’d established with Brandy and Monica’s shared hero Whitney Houston, saddled Monica with a lot of big, hammy ballads — a couple of Diane Warren-written songs, a cover of Ricard Marx’s 1989 chart-topper “Right Here Waiting.” Those tracks can be rough going, but Clive Davis also hooked Monica up with a few producers who had a better idea what to do with her. One of those producers was Jermaine Dupri.
By 1998, Jermaine Dupri was part of the pop establishment. Six years earlier, he’d broken in by discovering Kris Kross and by writing and producing their smash “Jump.” In 1998, Kris Kross were already done, but Dupri had stayed on top by producing rap-friendly R&B smashes for people like Mariah Carey and Usher. Dupri had become so successful as a producer that he’d started to think of himself as a rapper/mogul in the Puff Daddy mold. A couple of weeks after Monica released The Boy Is Mine, Dupri released his own album Life In 1472. On the single “Money Ain’t A Thang” — a collaboration with Jay-Z, a future subject of this column — JD bragged, justifiably, about taking small groups and turning them into big names. (“Money Ain’t A Thang” peaked at #52, even though I remember it being everywhere. Good song, regardless.)
Dupri had been the main producer on Usher’s 1997 breakout album My Way. Monica was on that album, though she didn’t work directly with Dupri. Instead, she and Usher duetted on a cover of “Slow Jam,” the genre-defining ballad that Babyface had co-written for Midnight Star in 1983; Babyface himself produced the Usher/Monica version. Clive Davis brought Dupri in to work on one song from The Boy Is Mine, and that song was the single that Monica released when “The Boy Is Mine” was still sitting at #1. The single was the right song for Monica at the right time. There’s no direct lineage between “The Boy Is Mine” and “The First Night,” but you could hear it as a sequel. Once you’ve established that the boy is yours, what do you do with him?
Jermaine Dupri co-wrote “The First Night” with Tamara Savage, a songwriter from Ventura, California who was only a year older than Monica. Savage had grown up in a strict Pentecostal house that didn’t allow secular music, but she snuck some in whenever she got a chance. While studying at junior collage, Savage made a living by recording demos, and that led to a songwriting deal. When she got together with Dupri to work on “The First Night,” Savage was just starting off as a songwriter; her only real credit before then was for co-writing “Take Me There,” Blackstreet’s Myá/Mase/Blinky Blink collab from the Rugrats movie soundtrack. “Take Me There” wouldn’t even come out until after “The First Night” had hit #1, so Savage was very much an unknown quantity. (“Take Me There” eventually peaked at #14.)
In Fred Bronson’s Billboard Book Of Number 1 Hits, both Savage and Dupri say that they wrote “The First Night” based on their own experiences. Savage says that she’d spent some time in New Orleans before arriving in Atlanta to work with Dupri and that she’d dated a guy there who wanted to move too fast. Dupri, meanwhile, claims that he came up with the title and that it resonated for him: “That was happening to me. I found out girls don’t really want to give it up on the first night.”
Dupri probably didn’t lend a whole lot of lyrical perspective to “The First Night,” but he did produce the song. For the beat, Dupri chopped up part of “Love Hangover,” the Diana Ross single that topped the Hot 100 in 1976, more than four years before Monica was born. “Love Hangover” is definitely a song about getting down, though Ross never specifies whether or not it’s on the first night. “Love Hangover” is a song in two parts: the languorous spaced-out opening and the euphoric disco climax. For “The First Night,” Dupri used a piece of that first part. Dupri’s beat is really a masterclass in late-’90s sampling, taking pieces of this instantly recognizable piece of music and warping it just enough that it dances around at the edge of your memory.
Like “The Boy Is Mine” before it, “The First Night” echoes the time-stretching strangeness that Missy Elliott and Timbaland were bringing to R&B in the late ’90s. Other than Diana Ross’ voice, everything from the “Love Hangover” intro is in there: the murmuring bass, the rumbling piano notes, the patient drums. But Dupri makes those sounds hiccup and stutter, working in these tiny climaxes to a track that was previously all buildup. He adds in jittery drum-programming and squelchy guitar notes. Different elements disappear and then reappear, flickering in and out of the mix. In the process, Dupri changes everything about “Love Hangover,” turning this song of tension-and-release anticipation into one that’s all unresolved tension. Because of the sample, the writers of “Love Hangover” — former Motown staff songwriters Marilyn McLeod and Pam Sawyer — also got credits on “The First Night.” I think it’s cool that McLeod, Alice Coltrane’s sister and Flying Lotus’ grandmother, got credit for writing a late-’90s R&B banger.
Unresolved tension is crucial to “The First Night.” Monica sings the song from the perspective of a girl on a first date who’s trying to decide how far she wants to let things go on this particular night. She’s attracted to this other person, but she’s also got a voice in her head that’s warning her not to do what she really wants — not because she’s moralistic or because she’s worried about infection or pregnancy but because she’s afraid of how this other person will see her afterwards: “Down to be open for some satisfaction/ Didn’t wanna say yes, afraid of your reaction.” Will you still love her tomorrow?
Monica sings the entire song to “you,” her date, but it’s pretty clear that her character isn’t saying any of this out loud. Instead, it’s an imagined monologue, and it’s all happening inside her head. She’s got her own hang-ups. Monica’s character wants to get physical, and she even convinces herself at one point that she’s in love, though she doesn’t dwell on that. She’s also got contradictory things happening internally. She thinks it would be wrong to get with this person, but it also feels right.
On the song’s intro, we hear Jermaine Dupri’s voice doing something that’s not quite rapping and not quite ad-libbing: “Baby, baby, tell me what’s up?” Maybe he’s supposed to be her date. (It’s fun to imagine Dupri using that line to figure out whether someone’s going to get down on the first night, then being shocked when it doesn’t work.) Other than that intro, though, we never hear from anyone else; Monica even sings all her own backup vocals. We hear her working though everything, realizing that she wants to get down. But the inner voice telling her not to get down on the first night wins out. On the bridge, Monica lays out what’ll have to happen for her to feel comfortable getting down: “If you want me, you got to know me/ And if you want my love, you gotta win my love.” Pretty reasonable!
It all seems simple, but for me, “The First Night” walks some difficult lines without ever losing its balance. “The First Night” isn’t a message song. It never gets preachy, and Monica never presents this decision as anything more than a personal thing. There’s no implied slut-shaming on the song, no talking down. But “The First Night” still addresses a real situation with a certain level of gravity and maybe even wisdom.
It helps that the song is catchy. There are big hooks on “The First Night,” and those hooks aren’t all in the tricky hall-of-mirrors beat. Monica has a strong, steely voice, and she sounds tough even when she’s puzzling out internal dilemmas. She sings a few fiery runs on “The First Night,” especially on the lovely bridge, but the runs never take center stage. Without ever sounding like she’s trying to rap, Monica rides the beat like a rapper, finding her own little rhythmic pockets on the track and sounding effortless and conversational. There’s real bounce and swagger in her delivery, and she uses her own multi-tracked vocals in smart ways. I like the way the lead and backup vocals come together to emphasize the line “don’t get down” on the chorus, highlighting this personal rule even amidst all the confusion that swirls around it.
“The First Night” sounded futuristic when it came out, and it still sounds pretty futuristic now. It’s very much an R&B song, but its speed and springiness make it work as dance-pop, too. The song started climbing the charts when “The Boy Is Mine” was still at #1, and Monica worked with “Boy Is Mine” director Joseph Khan on the video. In the clip, Monica and friends spend time with some boys, and she has fun blowing off her assigned dude. There’s also an excellent breakdancing showcase in the middle of the clip. More music videos should have that. “The First Night” ascended to #1 a few weeks after “The Boy Is Mine” fell from the top spot, and it was still at #1 when Monica turned 18 in October.
I love the kind of emotionally direct, technologically advanced R&B that swept in during the late ’90s and stuck around for a few years before dissipating into other sounds and genres. There’s a playfulness to songs like “The First Night,” even if the track itself is still serious. During a period when commercial rock music seemed like it was utterly out of ideas, the singers and producers and songwriters of the R&B world were testing out different sounds and ideas and approaches, figuring out how weird they could make their music sound before it got too weird. “The First Night” might not be the single best example of that trend at work, but it’s a damn good one. More would follow. We’ll see Monica in this column again.
BONUS BEATS: I don’t know why there’s never been a song with a big sample of “The First Night”; maybe it gets too complicated to sample something that’s already built on a sample. Instead, let’s go with Jermaine Dupri’s So So Def remix of “The First Night,” which had a completely restructured groove, as well as new vocals and lyrics from Monica and rap verses from Dupri and Rahman “Rocky” Griffin. Here it is:
(As lead artist, Jermaine Dupri’s highest-charting single is the 1998 Da Brat collab “The Party Continues,” which peaked at #29. As a guest, JD got to #15 when he, Brat, and Bow Wow rapped on Dem Franchize Boyz’ “I Think They Like Me” in 2005.)
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.