Y2K popstars: Britney Spears, Mandy Moore, Christina Aguilera, Jessica Simpson | Explainer

Pop music may be all about Taylor Swift right now (and for the foreseeable future, given her upcoming Life of a Showgirl release in October).

But back in 1999, it was all about a quartet of blonde cookie-cutter teenage girls competing to be the Queen Bee of the lucrative pop music world.

Britney Spears, Christina Aguilera, Mandy Moore and Jessica Simpson came to define the era before the turn of the millennium, dubbed Y2k.

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Former Mickey Mouse Club stars Spears and Aguilera were pitted against each other from the start, being signed by competing record labels as each’s answer to the candy pop market.

Spears was signed by Jive Records and Aguilera to RCA Records, although both labels were ultimately part of BMG.

Meanwhile, Moore and Simpson were signed to Epic Records and Columbia Records, respectively – both offshoots of Sony Music.

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Spears was 16 when she released her first single, Aguilera was 18 when her first song hit the charts, Simpson was 19 for her debut release and Moore was the youngest, just 15 when her first single launched.

All four teens released their debut albums in 1999, with Spears’ …Baby One More Time arguably the most successful of the lot.

Let’s take a look at who they are, how they did and what they’re up to now.

Jessica Simpson

Jessica Simpson was the last of the four to arrive at the pop princess party, releasing her first single I Wanna Love You Forever on August 30, 1999.

Her debut album Sweet Kisses then dropped at the end of November.

The singer grew up singing in the church of her minister father, Joe, who become her manager and spoke openly about her faith and saving herself for marriage.

She dated 98 Degrees lead singer Nick Lachey and after marrying in 2002, the pair had a reality TV series Newlyweds: Nick & Jessica.

The show lasted three seasons and turned the pair into a power couple of the early noughties.

However, they split in November 2005.

Simpson’s star and success paved the way for her younger sister Ashlee to make her debut on the charts with Pieces of Me, released in 2004.

In 2005, Simpson made her movie debut in The Dukes of Hazzard, starring as Daisy Duke and, in the process, shedding her good girl image and presenting a sexier version of herself.

However, her acting career never quite took off beyond that big-budget film.

Simpson continued to release music, but her real success has come from her self-named fashion empire.

What started as a shoe collaboration is now a $1 billion brad, which includes shoes, accessories and perfumes.

The singer also re-married and had three kids – Maxwell, Birdie and Ace – with Eric Johnson before the couple announced their split in January, after 11 years of marriage.

Mandy Moore

The Candy singer exploded onto the scene in August 1999, just a week before Simpson, and launched her debut album So Real a week after (don’t forget, they basically had the same record label, so their launches were carefully staggered).

But Moore’s true passion and career success came from her pivot to acting – she’s arguably more successful as an actress than a singer but has, on occasion, mixed the two, like in the animated Disney movie Tangled.

Moore almost stole scenes from Anne Hathaway in The Princess Diaries and went on to earn Emmy and SAG Award nominations for her role in the hit drama series This Is Us.

Her focus on acting led to a decade-long hiatus from music.

She released the album Silver Landings in 2020, 11 years after her previous album, 2009’s Amanda Leigh.

In a recent appearance on Kylie Kelce’s podcast Not Gonna Lie, Moore described herself as the “boring” one of the four young pop stars.

“I feel like I was the youngest and the most boring … out of the four of us,” she told Swift’s fiance’s sister-in-law.

Moore recalled she didn’t really interact with Spears, Simpson and Aguilera.

“I would never have been able to cross paths with them,” she said, “They were, like, superstars. They were on this level of success that I’ve never known.”

Moore, who was previously married to singer Ryan Adams, is married to musician Taylor Goldsmith and the couple have three kids.

Christina Aguilera

Her first official single hit the charts in May 1999, but Aguilera had technically had a single before that, recording the song Reflection for Disney’s Mulan soundtrack in 1998.

The ballad went on to become the theme song for the animated film but it didn’t quite launch the pop star’s career. However, in honour of it being her first single, Aguilera re-recorded the song in 2020 for the live action remake.

The sultry and breathy Genie in a Bottle was a bit of a slow burn for Aguilera and went to the top of the Billboard Top 100 a couple of months after its release in the US.

In Australia, it earned the No. 2 spot on the ARIA charts and Platinum sales status along the way.

Interestingly, her self-titled debut album peaked at No. 22 on the ARIA charts but got up to No. 8 on the Australian Dance Albums chart.

In the US, she continued to hit the high notes on the charts with her next three singles – What A Girl Wants, I Turn to You and Come on Over Baby (All I Want is You) – and What A Girl Wants was even nominated for a Grammy Award.

Aguilera went on to beat out Spears (as well as Macy Gray, Susan Tedeschi and Kid Rock) to win the Best New Artist category at the 2000 Grammys ceremony.

Despite all of her success, Aguilera retreated from the spotlight before releasing her second album, the deeply personal Stripped, in 2002.

When she reemerged, Aguilera had completely overhauled her image from blonde teen to brunette woman, complete with leather chaps in the raunchy music video for Dirrty, which was met with huge criticism at the time.

Aguilera fought to write songs on and executive produce her sophomore release, after speaking out about not being allowed to have a say on her first album.

It feature more R&B vibes with a Latino feel and wasn’t the commercial pop album her record company supposedly wanted her to make, but it topped the US charts and earned her five Grammy Awards.

In total across her music career so far, Aguilera’s had five wins off 21 Grammy nominations.

It would be another four years before Aguilera morphed her image again, this time into a 1940s screen siren for her fun and flirty album Back to Basics in 2006.

(Sorry, kids – Xtina, as she’s now known, had eras before TayTay came onto the scene!)

In that time, she got engaged and married to her first husband, music executive Jordan Bratman, and the couple welcomed a son shortly after, in 2008. The relationship ended in 2010.

Later that year, while working on the movie musical Burlesque – her first and only major film role to date – Aguilera met production assistant Matthew Rutler.

They got engaged on Valentines Day 2014, a few months before they welcomed their daughter. They’re clearly in no rush to get married, though, with the nuptials still pending a decade later.

While she’s still making music, releasing new albums every couple of years, a lot of the singer’s time has been taken up playing mentor to young new artists.

That’s largely thanks to her role on The Voice (US), where she’s been a coach on and off since 2011.

Britney Spears

Britney was the OG of the pop princess quartet, getting first out of the gates in 1998 with the release of her debut single …Baby One More Time.

The catchy pop track, written and produced by Swedish powerhouse Max Martin, became a chart-topper right around the world, selling three times platinum in Australia.

The music video, set at the same Venice Beach High School where the movie Grease was shot, went on to become iconic – with Spears’ schoolgirl outfit serving as a popular Halloween costume.

The song earned her a Grammy nomination for Best Female Pop Vocal Performance but it would be six nominations and five years later before she won her first statuette, in 2004 for Toxic.

While she missed out on the Grammy, Spears won a Teen Choice Award, MTV Video Music Award, MTV European Music Award (EMA), as well as a Billboard Music Award, which cemented her status in the music industry.

Like her counterpart Simpson, Spears was dating a boyband member – her former Mickey Mouse Club star, Justin Timberlake, who by the late ’90s was part of *NSYNC.

The childhood sweethearts-turned-teen romance thrust the couple into the spotlight and on the front pages of many magazines.

In light of Simpson’s comments around her virginity, pressure mounted on Spears to announce the status of her own, something she later talked about in her memoir as being a bizarre position to be in as a 19-year-old.

Spears also revealed in the 2023 memoir The Woman in Me she became pregnant with Timberlake’s child during those years but was pressured into an abortion.

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However, that all stayed behind closed doors until the singer’s public halo tumbled following the couple’s split in 2002.

Timberlake accused Spears of cheating on him and sleeping with another man through his song Cry Me A River and the accompanying music video – all of which was in contrast to Spears’ squeaky-clean image up to that point.

During this time, Spears worked her butt off as music execs tried to capitalise on her fame and success following her first album, also titled …Baby One More Time.

Where Aguilera took years off to make her next album, Spears had already released another two, with Oops!… I Did It Again in 2000 and Britney in 2001. In the Zone followed in 2003 before a four-year hiatus.

In October 2004, Spears married backup dancer Kevin Federline after less than three months of dating.

They hosted a secret wedding they’d told family and friends was an engagement party.

In September 2005 they welcomed their first son and in September the following year, their second son was born.

Spears returned to the music scene with Blackout and Circus in 2007 and 2008 respectively.

She even embarked on a world tour of the latter album, but fans could see something was not right with the star.

In January 2008 she was rushed to hospital over concerns around her mental health after claims she was not relinquishing custody of her sons to their dad, who by then was Spears’ ex-husband following a messy split and custody battle.

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Spears was placed under a conservatorship that would last until November 2021, despite the singer’s numerous legal bids to end it earlier.

A movement spread among fans, called #FreeBritney, mounting pressure on the popstar to get a fair trial and to be heard in her own words.

In the meantime, Spears stopped making music and performing as a silent protest until her successful legal bid.

In her memoir, Spears opened up about those years, being medicated and the restrictions placed on her, shocking many fans.

While Spears has said she’s done making music, Charli XCX confirmed she had been asked to write a song for the popstar.

While nothing’s come of it as yet, the comeback of the century for the OG pop princess could be right around the corner... and just maybe, it will rival Swift’s chart domination.

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