[Just the top 20, as I couldn’t bring myself to write about more; I’m not generally a big fan of the pop of this era.]
1 — I DON’T WANT TO MISS A THING –•– Aerosmith – 1 (1) — They should really be ashamed of this hot garbage, but I doubt Steven Tyler is ashamed of anything. His bandmates, however… (And most of the blame, of course, goes to songwriter Diane Warren, who even at her schlockiest is better than this.)
2 3 THE FIRST NIGHT –•– Monica – 4 (2) — Now, this is the stuff. At the end of the ’90s, Jermaine Dupri was one of the straight-up dons, and Monica was one of his top priorities — for good reason. That voice, just oozing with sass and class, was capable of toplining just about any song, and Dupri wisely had her follow up her half of “The Boy Is Mine” (#5, below) with this “Love Hangover”-jacking insta-classic about not “get[ting] down [on] the first night.” It’s gross and unfortunate that “The Boy Is Mine” was knocked off the top by Aerosmith’s bleating ballad; it would’ve been beautiful serendipity for Monica to replace herself at #1. That said, after four weeks stuck in the runner-up position (weirdly, the entire top 5 stayed static for the month of September), this punched its way to #1 and spent a fortnight there.
3 4 CRUSH –•– Jennifer Paige – 10 (3) — A lovely, frothy little bonbon of pop, but not as transcendent as I’d remembered. Where this is good, Donna Lewis’s “I Love You Always Forever” (to compare it to another female-voiced one-hit wonder) is great.
4 2 MY WAY –•– Usher – 12 (2) — Jermaine Dupri, as I noted above, made a lot of great records in the late ’90s, but this wasn’t one of ’em. This is a fairly tacky song in which Usher, getting old before his time, tells his rivals that their girlfriends like it, uh, his way. The song is both too simplistic (it sounds as if it’s based around a Casio preset) and too busy (Dupri won’t stop shouting in the background, a la Puffy) at the same time. Both Usher and Dupri are better than this.
5 1 THE BOY IS MINE –•– Brandy & Monica – 15 (1) — I’ve previously written of this single, “Darkchild and Dallas Austin teaming up to make absolute musical magic behind the boards, supporting Brandy and Monica making magic of their own, like Babs and Donna did 19 years earlier. This is the plushest, friendliest catfight ever.” This “Boy” spent 13 well-deserved weeks at #1, a feat only 10 other singles (most recently, of course, “Despacito”) [as of this writing] have ever accomplished. Brandy’s smooth coo meshes marvelously with Monica’s grittier vocals; even though Brandy’s first single had only come out in 1994 and Monica’s arrived the following year, both exhibit the self-assurance of seasoned pros here. One of my favorite singles of the decade.
6 7 YOU’RE STILL THE ONE –•– Shania Twain – 30 (2) — It’s so sad how Twain’s marriage to “Mutt” Lange ended, because you can really feel the genuine emotion and love in not just the lyrics, but her vocal performance of this song. This is an immaculately crafted and produced love song, one which, like it or not, will be played at weddings and anniversary parties for decades and decades to come.
7 6 ADIA / ANGEL –•– Sarah McLachlan – 15 (3) — The ’90s, musically, were bad for a lot of reasons, but here’s a good one: the return of double-sided hits! It wasn’t really so far, in retrospect, from 1989’s “Vox” to McLachlan’s 1998 status as The Queen of Lilith (and the burgeoning Adult Top 40 format); sure, early McLachlan was a bit more Kate Bush and a bit less campfire singalong, but apart from that? You can hear the well-meaningness in her voice, and I like that. This isn’t some phony bullshit: she means it, maaaaaan. “Adia” is a lovely, loping reminder that “we are still innocent” (I’m not sure what that means, but okay), while “Angel” is a gorgeous, aching piano ballad on which you can almost hear McLachlan’s voice crack several times. I like, and will defend, them both.
8 8 DAYDREAMIN’ –•– Tatyana Ali – 5 (8) — A rote R&B record that interpolates the same riff from Steely Dan’s “Black Cow” that Lord Tariq & Peter Gunz used earlier in the year for their own “Deja Vu (Uptown Baby)” — and just to drive it home, Tariq and Gunz appear on this. I mean, come on. That’s about all we should expect, though, from a singer/starlet who gained fame as an actress on The Fresh Prince of Bel Air.
9 5 NEVER EVER –•– All Saints – 7 (4) — All Saints are legends in their home of the UK: a home-grown girl group who released nine singles, every one of which hit the top 10, with five of them going to #1. That’s an incredible strike rate. And some of those, like 2000’s “Pure Shores,” are absolute pop classics. So why is “Never Ever” — their first UK #1 and their only hit of any significance in the US — so goddamn drippy? This is a bland-as-cream-of-wheat girl-group ballad with a remarkable deficit of soul.
10 11 WHEN THE LIGHTS GO OUT –•– Five – 14 (10) — Another British phenom: Five had 11 hits in the UK, and all 11 of ’em hit the top 10. And like with the preceding single, this was their only bite of the hit apple in the US. However, unlike “Never Ever,” this is premium TRL fodder, an excellent (well, except for that “rap break”) boy band record on par with “Everybody (Backstreet’s Back),” if not “Pop.” It would, alas, get no further on the chart, and they’d never bother us in the US again.
11 10 CRUEL SUMMER –•– Ace Of Base – 8 (10) — Until I started my research for this chart, I had no idea that Sweden’s second-biggest musical exports had covered Bananarama’s 1984 gem. This version is not such a gem, however, nor is it a jam. It’s an identikit shiny, happy, pop record, scrubbed of any and all personality. Much like Ace of Base themselves.
12 12 LOOKIN’ AT ME –•– Mase Featuring Puff Daddy – 7 (12) — On its way to a high of #8, this would be Mase’s final top 10 single. He should’ve been happy to play sidekick to Puff, because goddamn, his solo work was terrible. This is an early Neptunes production, which I hope for their sakes they’ve expunged from their discography. The track is dull, and Mase is even duller.
13 14 TIME AFTER TIME –•– INOJ – 3 (13) — Another record touched by the hand of Dupri, this bass remake of Cyndi Lauper’s indelible classic was the second hit cover version from INOJ (the first being her take on Ready for the World’s “Love You Down”), a Wisconsin singer whose fame came just from appearances on So So Def Bass All-Stars comps. But hey, this made it all the way to #6 pop, so she grabbed that brass ring for a couple minutes. As for the song itself, you needn’t trouble yourself with it.
14 9 TOO CLOSE –•– Next – 30 (1) — 5 weeks at #1, 53 weeks on the Hot 100, and the #1 pop single of 1998: not bad for an R&B trio’s second single. Lyrically, this is kinda gross — really, guys, I don’t need to hear about your erections — but musically, Naughty by Nature’s Kay Gee made a superb track over which Next could sing about their boners. It’s rooted in a sample from Kurtis Blow’s “Christmas Rappin’,” and is one of the smoothest R&B singles of its era, which is precisely why it endures [over 25] years later.
15 13 MAKE IT HOT –•– Nicole Featuring Missy “Misdemeanor” Elliott & Mocha – 11 (5) — From the era when everything Missy touched turned to gold (records), this fair-to-middling R&B record (produced by Timbaland, of course) by a fair-to-middling singer and featuring, in addition to Elliott, a fair-to-middling (if that) rapper, this just further proved that Missy was in the midst of her Imperial Phase. Her coattails could bring anyone a hit, even if it wasn’t particularly compelling. Spoiler alert: the best thing on this is Missy’s bridge.
16 16 THIS KISS –•– Faith Hill – 25 (16) — A great Beth Nielsen Chapman song (she had two co-writers, but to me this is thoroughly a Chapman song) gets a sterling, big vocal from Hill and great production from Hill herself and Byron Gallimore — this sounds big, and even though it crossed over to #7 pop and #3 AC, it never sounds less than country (where it, of course, hit #1, her fifth to date). This is a song of pure joy, and everything about it delivers.
17 18 I STILL LOVE YOU –•– Next – 5 (17) — The follow-up to “Too Close” couldn’t help but disappoint, getting to #14 pop/#4 R&B on the fumes of its predecessor. It’s truly generic R&B in every way that “Too Close” wasn’t.
18 15 FRIEND OF MINE –•– Kelly Price – 8 (12) — Don’t hold R. Kelly against this single, a fine tale of infidelities (her BFF is creepin’ with her man) which R. had a hand in the production and writing of (but not the only one). But what makes this record a triumph is Price’s huger than huge voice, which can truly sing it all. Not a year later she’d have a featured role on Whitney’s “Heartbreak Hotel” — that’s how good she is. Price’s material often isn’t worthy of her, but this “Friend” is. (5 weeks #1 R&B, too.)
19 — THINKIN’ BOUT IT –•– Gerald Levert – 1 (19) — Gerald Levert was a master at making au courant R&B that was still very much grown-folks music. The stats back me up: in his post-Levert (the hit trio he started in the mid-’80s who peaked, pop-wise, with 1987’s “Casanova”) solo career, his first eight consecutive solo albums, between 1991-2003, all peaked in the top 2 on the R&B chart, and in that same stretch he hit the R&B top 10 with 10 singles, including a trio of #1s. This came close, peaking at #2 (and #12 pop, thanks to its strong sales), and is one of his best. It’s a strange single, basically a Dan Savage column in musical form, with Gerald singing to his lady that he knows she’s sleeping around on him (and that payback is a mother), along with an odd lyric about “that I should share your underwear” — after [over 25] years I’m still not sure what that’s about. Musically this is very much of its moment, ultra-contemporary, but yet doesn’t sound remotely dated. We lost quite a talent when he died in 2006 at only 40 years old; there’s no doubt in my mind that, were he still alive, he would be the king of Adult R&B right now. [I just discovered that deep house eminences Blaze remixed this single at the time; if you love deep house like I do, you’ll want to hear this.]
20 17 COME WITH ME –•– Puff Daddy Featuring Jimmy Page – 11 (4) — Talk about an Imperial Phase: Puff got so big (and so fast), he could bring in Jimmy Page (and, in a less well-known role, Tom Morello) to replay chunks of Led Zep’s “Kashmir” for a shitty Godzilla soundtrack single. And it is as ponderous as “Kashmir,” only without any of the interesting parts. [Interesting that this is the only single in this top 20 missing from streaming - though of course, that’s only right considering its maker.]