In re-examining Britney’s sophomore album, there’s one outlier from the group of four released singles:  “Don’t Let Me Be the Last to Know,” selected at the last minute as the replacement for the original choice for the fourth single (“When Your Eyes Say It”) was obviously intended to capitalize on the buzzworthy co-writing credit of a certain Canadian country-pop crossover icon and her husband. Shania Twain and her then-husband, Robert John “Mutt” Lange, however, couldn’t deliver a hit ballad for Britney at the time, and in considering what better choices were available, I’d throw my money behind “Where Are You Now?”—one of Britney’s loveliest ballads and seemingly the first vocal showcase in her discography.

Related RX: The Hits That Got Away From Every Britney Album: “I Will Be There”

Jive Records had the right instinct at the time in selecting a ballad for the fourth single, but both their early choices overlooked this neglected gem. “Don’t Let Me Be the Last to Know,” despite reportedly being one of Britney’s personal favorites, sounded both too similar to a Shania Twain record and too far removed from Oops!… I Did It Again’s two major strengths, it’s R&B-infused bops and the lush ballads. But “When Your Eyes Say It,” for all its seductive slow-burn sexiness, would have bombed too. Diane Warren’s schmaltziest lyrics turn up for a track that felt both too racy at the time and too tame in retrospect. It’s an enjoyable track, but it lacks the panache of “Where Are You Now,” penned by Max Martin, of course, and Andreas Carlsson.

At the end of the Oops era, this ballad would have been a welcome change of pace, and arguably would have stood out more than a more obvious choice like “Don’t Go Knocking On My Door,” albeit one of the album’s best tracks and by far the single song providing the biggest clue about the more urban routes Britney would go next with her third album. As Britney confided to MTV at the time, in general her second record was “much more funkier and edgier. And, of course, it’s more mature because I’ve grown as a person too.” Coming off the third single, “Stronger,” however, a palate cleanser was in order. Its predecessor, “Lucky” was a superb midtempo anthem, the “ultimate mallrat teenage bittersweet symphony,” as NME described it at the time in their 8/10 review of Oops!

But “Where Are You Now?” checked just as many early 00s boxes for radio-ready **********: heartbreak-infused lyrics? Check. Carefully calibrated chorus? Check. Ballad-building transitions? Check. This was, after all, the year of ballads such as the Backstreet Boys’ “Show Me the Meaning of Being Lonely,” Faith Hill’s “Breathe,” and Christina Aguilera’s “I Turn To You,” all among the most successful songs of the year on Billboard’s year-end chart.

Speaking of Aguilera, the vocals seem like the best place to begin in pinpointing just why this song would have been a hit. In the context of Spears’ peers, “Where Are You Now” sounds like any number of big-moment power ballads from the likes of Aguilera, Whitney Houston and Celine Dion, herself still riding the wave of goodwill from Titanic at the turn of the century. All three performers come to mind in the sublime centerpiece of the song, at the 3:13 mark when a choir enters for the first time to belt the beginning of the “Where are you….” Line; but it is Britney who returns for that finishing “Now,” and boy does she show up. “Everytime” may boast the softer side of Britney’s voice with her heartbreaking falsetto, but this moment is surely the most impressive recorded belt in Britney’s discography. The track explodes around her voice as she holds the note for several seconds before descending into those trademark “uh-uh-uhhh-uhhhh” nasal equivocations that Vocalney keeps on standby. Significantly, this moment does not feature a run—it’s distinctive specifically because it is a high note for Britney’s lower register, and for the vocal strength in holding the note à la Dion, who pioneered the wall-of-sound approach to reaching a note and delivering it without the slightest hint of vibrato. It’s a welcome sign that critics, even then, found something to appreciate in the simplicity of Britney’s vocals, which could be regarded at the time as “a relief compared to Aguilera’s numbing vocal gymnastics,” to borrow from EW’s David Brown in his review of the album.

Martin’s production of the track clearly embraces this appreciation for what a Britney ballad could mean. It’s the longest track on the album, indulging in almost an entire minute of gorgeous harmonies as Brit and the choir harmonize over the chorus repetitions before the song slowly fades out—an outro practically engineered for school slow dances a generation ago. Importantly, however, the track earns that big crescendo and the luxurious outro through a gradual ascent. It opens with Britney’s voice alone and classic percussive flourishes that code “ballad moment”—but each of them refrains from the saccharine context of lesser tracks like “From the Bottom of my Broken Heart.” This song, like my pick for last week’s hit that got away (“I Will Be There”) is among the most mature songs on the record. (Spoiler: next week’s has the same quality, but it’s not a ballad!) The acoustic guitar weaving throughout the first few minutes of the track and taking center stage at the 2:40 mark is far more effective than the absurd twang opening “Don’t Let Me Be the Last to Know,” for instance, and the lyrics are better too. In fact, they arguably anticipate the Britney ballad, “Everytime,” echoing the lovelorn confusion of heartbreak in that song but speaks from the opposite perspective. Britney is the lover who supposedly strayed in the In the Zone track, but here she is the lover searching for someone who has gone. “Where is your heart / when I’m not around?” she sings, as though in suspicion. That heartache is what prompts the track’s big shift around the 3:00 mark, when Britney lets it all out and reaches for the rafters of her range.

It’s a standout moment on an album that has aged surprisingly well. Little wonder it took 15 years for another female artist to exceed the 1.319 million units sold in Oops!’s debut frame, a record attached to her name for so long that the staggering numbers of Britney’s sophomore era sometimes obscure the real growth demonstrated on the album. Sure it sold almost 25 million copies worldwide, but it also was an unmistakable, early sign of Britney’s ambition, which, as Rob Scheffield described in his admiring review of the album for Rolling Stone, was complex, fierce and downright scary, making her a true child of rock & roll tradition.”

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