Britney Spears Network: Billboard’s Greatest Pop Star of 1999: Britney Spears

(In 2018, the Billboard staff released a list project of its choices for the Greatest Pop Star of every year, going back to 1981. Read our entry below on why Britney Spears was our Greatest Pop Star of 1999 — with our '99 Honorable Mention runner-ups, Rookie of the Year and Comeback of the Year pop stars at the bottom — and find the rest of our picks for every year up to present day here.)

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Britney Spears' debut single "…Baby One More Time" hit No. 1 on the Hot 100 the week of Jan. 30, 1999, kicking off a year that radically transformed modern pop. "Baby" spent a mere two weeks on top, and Spears didn't come close to replicating its chart success within that year: "Sometimes," her second single, topped out at No. 21, while "(You Drive Me) Crazy" wound up peaking at No. 10. While certainly respectable, these chart positions in no way reflect how thoroughly Britney Spears dominated the pop culture of 1999.

In a way, Britney Spears's rise is analogous to the other pop phenomenons of the 1990s, trends that were incubated in the underground only to explode in the mainstream. Noisy, dangerous and defiant, alternative rock and hip-hop's ascendency dominated the decade, obscuring how a commercial counter-culture developed in their shadow. Where grunge and rap were to some extent grassroots movements, the teen-pop revolution was cannily constructed by the industry. Anchored on Nickelodeon and Disney Channel, this unabashedly pop movement picked up where New Kids On The Block and New Edition left off, updating bubblegum with new jack rhythms and corporate pizzazz. Spears cut her teeth here as part of the '90s incarnation of The Mickey Mouse Club, a place where she learned how to sing, dance and be a star.

The latter is an essential element of Britney's stardom in 1999. Her fellow MMC alum Christina Aguilera actually performed better on the Billboard charts than Spears, racking up three No. 1 hits from her eponymous 1999 debut — but her success was overshadowed by Britney. Much of that was due to the sun-blocking enormity of "Baby": The atomic midtempo anthem quickly proved pivotal for turn-of-the-millennium pop, with its hip-hop and R&B influences officially turning the page on the Eurodance-based top 40 of the earlier decade. It quickly cemented writer/co-producer Max Martin as the defining sonic architect of the moment, and became one of the most iconic songs of the turn of the millennium, spawning countless imitators in its wake.

A large part of Spears' rise was also due to her savvy manipulation of imagery — a gift showcased in the teasing music video for "Baby," which featured Britney slinking through high school hallways dressed as a schoolgirl. The video caught fire on MTV thanks in no small part to Total Request Live, with the clips for subsequent singles "Sometimes" and "(You Drive Me) Crazy" following it to regular play near the countdown's top. Britney's popularity is inextricably tied to the TRL era: Neither would've been as big a sensation without the other.

Like all great pop stars, separating the image from the music was impossible with Britney Spears. Magazine photoshoots leaned into her provocative sexiness — her 1999 cover for Rolling Stone found her dressed in hot pants and cuddling a Teletubby — but she spent as much time working wholesome ground. Learning her Disney channel lessons well, Spears threw herself into the industry machine, appearing regularly on television and at mall events. Even "(You Drive Me) Crazy" received a boost from its appearance in the teen comedy Drive Me Crazy, the synergy suggesting how Spears was part of a smooth-running machine.

All of these avenues had been around for decades, but in 1999, the clean efficiency of Britney Spears' cross-platform pollination felt revolutionary. …Baby One More Time was the organizing force behind a series of multi-media events that sold Britney's stardom as much as the music itself, an idea that flourished in the social media-saturated 21st Century.

Honorable Mention: Backstreet Boys (Millennium, "I Want It That Way," "Larger Than Life"), TLC (FanMail, "No Scrubs," "Unpretty"), Ricky Martin (Ricky Martin, "Livin' La Vida Loca," "She's All I Ever Had")

Rookie of the Year: Eminem

The biggest hit he had in 1999 was his debut single "My Name Is," which just scraped the top 40, placing no higher than 36. Still, there is no question that Eminem dominated the areas of 1999 that weren't defined by Britney Spears or BSB. Furious and funny — and thanks to producer Dr. Dre, quite funky — The Slim Shady LP courted controversy from all quarters. Eminem's violent, provocative imagery provided a lightning rod in 1999 but underneath that bluster, he proved himself a dextrous, quick-witted rapper — and his angst appealed to adolescents who would've been listening to grunge earlier in the '90s.

Comeback of the Year: Cher

Cher had long been a beloved figure in pop culture, but she never was quite hip. From her early days with Sonny Bono through her MTV-era arena-rock comeback, Cher's signature was enlivening a stuffy art form, which is why "Believe" was such a shock: It found her embracing dance so thoroughly, she fed her voice through an Auto-Tune audio predecessor. Largely treated as a novelty at the time, the robotization of Cher's voice had a lasting impact, with legions of singers and rappers adopting the innovation well into the next century. "Believe" had already topped the Hot 100 by early 1999, but its momentum rarely slowed throughout the year: Even when "Strong Enough" was released as a second single, "Believe" remained dominant, not only ruling the airwaves but propelling Cher's career for the next two decades.

(Read on to our Greatest Pop Star of 2000 here, or head back to the full list here.)