How Britney Spears Made The VMAs Her Vehicle For Transformation

The pop star used the awards show as an opportunity for risks, rewards, and redemption

Since the first MTV Video Music Awards went down at New York’s Radio City Music Hall in 1984, artists have treated the stage like a blank slate. Some mount Broadway-level productions (Lady Gaga’s cinematic “Paparazzi” from 2009), while others literally mount the damn stage (Rage Against The Machine’s Tim Commerford protesting Limp Bizkit’s win in 2000). There are the artists who test the limits of broadcast censorship (Madonna’s iconic “Like A Virgin” routine at the inaugural ceremony; Nirvana’s “Rape Me” in 1992), and those who celebrate their careers with jaw-dropping retrospectives (still recovering from Beyoncé’s in 2014, to be honest).

It’s not unusual for a notable — or notorious — VMA moment to stand out as one of the most important in an artist’s career, nor is it weird for them to synch up with other massive milestones for the performers, like historic record sales, or, y'know, the birth of their first child. By that metric, no other artist has had a connection to the heart of the VMAs quite like Britney Spears.

Looking back at her VMA performances and appearances, starting with her debut in 1999, we noticed that each one signifies a turning point for the pop star. Here’s a closer look at Britney’s VMA moments and how they factor into her story, from ...Baby One More Time to her imminent Glory.

1999: “...Baby One More Time”

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1999 MTV Video Music Awards

Britney’s breakthrough hit, “...Baby One More Time,” had established itself as one of the strongest singles of the decade by VMA night in 1999. Her debut album of the same named had dropped earlier that year on January 12, 1999, and broke tons of records in the following weeks. With ...Baby One More Time, Britney became the first female artist to have the top single on Billboard’s Hot 100 and the top album in the country at the same time on January 30, 1999. Moreover, she was the first artist, period, to dominate both categories with her very first album.

She’d go on to score her first Rolling Stone cover, become the best-selling artist of 1999, and the youngest artist to earn a diamond certification once sales for ...Baby One More Time passed the 10 million mark. “...Baby One More Time” was the last music video to ever be played on Total Request Live, so, yeah: There was a whole lot more wrapped up in Britney’s first VMA appearance than her smash hit.

Before she arrived at the Metropolitan Opera House on September 9, 1999, MTV followed Britney as she shopped for her VMA looks, where she picked up some safety panties and perfected her outfits for the red carpet and the stage. For the show, Britney stuck with a classroom vibe similar to the video itself, jumping on desks and working in a more difficult dance break for the big event. Her performance immediately segued into one with her pals NSYNC. She didn't bring home any Moonmen that night (in spite of her three nominations), but if we needed footage of two live acts performing together for some kind of millennial time capsule, this Britney/NSYNC double-feature would totally be it.

2000: “Oops! ...I Did It Again”

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2000 MTV Video Music Awards

For her next VMA appearance, Britney not only upped her nomination count — she got four Moonmen nods for “Oops! ...I Did It Again” and “(You Drive Me) Crazy,” too — but also the shock factor with her megawatt striptease.

In the months leading up to the performance — which had Britney ripping off her suit, tossing off a fedora, and completely captivating the audience with her moves — Britney continued to break records and build a foundation for lasting pop prowess. She shared the behind-the-scenes process behind both of her VMA-nominated videos on Making the Video in memorable episodes. Oops! ...I Did It Again was released on May 16, 2000, with 1.3 million copies of the album flying off the shelves in its first week, making it the best first week for an album by a female artist. (She'd hold onto that title until 2015, when Adele returned with 25 and trounced that number with a $3.38 million sales week.)

And on top of all that, Britney and Justin Timberlake confirmed they were dating. The couple attended the VMAs together that year, and while Brit absolutely held the spotlight on her own, the additional interest in her personal life made that light shine ever hotter.

2001: “I'm A Slave 4 U”

For the live premiere of this Britney single, pop's reigning princess pulled out all the stops. She gave New York's Metropolitan Opera House a surreal makeover once more, but instead of turning the stage into a high school classroom, she brought in jungle cats, a sultry scene with writhing dancers and swaying trees, and a giant python that she hiked over her shoulders for a portion of the performance.

If her striptease to “Oops! ...I Did It Again” the year before was any indication that Britney was moving in a more adult direction, “I'm A Slave 4 U” solidified it in subject matter, its darker, mysterious, and bass-laden tone, and the sexy-as-hell visuals that went along with it. Instead of focusing on the prior year's achievements at the VMAs, this was the first time Britney used the show to kick-start a new phase in her career.

The months that followed brought about the premiere of Crossroads, her first major motion picture. As far as the album was concerned, Britney didn't quit with the record-breaking streak with her third full-length: Britney would debut atop the Billboard 200, thus cementing her status as the first female artist with three records to hit No. 1.

2003: “Like A Virgin”

2003 MTV Video Music Awards - Show

Ah, The Kiss: People have smooched at the VMAs before, but when you say “VMAs” and “kiss” in the same sentence, you're likely referring to the shocking moment from the 2003 opening performance that had Britney, Madonna, and Christina Aguilera locking lips. Once again, the VMAs would serve as a jumping-off point for Britney, as In The Zone would see its release about 10 weeks after the broadcast. The first single? “Me Against The Music,” her Madonna-featuring track, which would hit the airwaves six weeks after the VMAs.

Professionally, Britney was killing it: In The Zone gave us “Toxic,” one of her most adored singles, and the one that would ultimately net Britney four VMA nominations (and her only Grammy Award, for Best Dance Recording in 2005). In The Zone debuted at No. 1 on the Billboard 200, thus dubbing her the first female artist to have four consecutive albums at the top of the charts.

2004-2006: Britney Off-Stage (But Not Out of the Spotlight)

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Britney Spears and Kevin Federline

With the exception of her first compilation, Greatest Hits: My Prerogative, Britney steered clear of the studio following the intensely prolific run of her first three records. After her 2002 breakup with Timberlake, Britney got married in January of 2004 to Jason Alexander, an old friend from her native Louisiana. The marriage lasted less than 60 hours, and later that year, after a three-month engagement, Britney married dancer Kevin Federline.

Britney didn't come to the 2005 or 2006 VMAs, as she and Federline had their hands full with their growing family: Their oldest son, Sean Preston, was born on September 14, 2005; Jayden James, his little brother, was born on September 12, 2006. (Brit and K-Fed did make an appearance via satellite at the 2006 VMAs in Miami, though.)

2007: “Gimme More”

2007 MTV Video Music Awards for - Show

Context is key, and it's important to note two things about Britney's show-opening performance of “Gimme More” at the 2007 VMAs in Las Vegas: This moment occurred in the middle of a definitively dark time for the pop star, and it was the beginning of a period that would ultimately result in not only some of her strongest work, but hardest-earned triumphs.

The VMAs occurred smack in the middle of a gnarly vortex that saw the dissolution of her marriage and an onslaught of personal and professional problems, which absolutely had an impact on the performance she delivered. As she'd done at the 2003 and 2001 VMAs before it, Britney used the VMA stage as a launchpad for her next musical mission, with “Gimme More” — the first single from Blackout — as her vehicle for change. While the performance itself was off, Blackout, which came out on October 25, 2007, would go on to become a fan favorite and a sleeper hit, one that offered mature, highly danceable singles, and the song that would help get her back on her feet, “Piece of Me.”

2008 was kinder to Brit, largely thanks to the success of “Piece of Me”: She would win her first three Moonmen at the 2008 VMAs — Video of the Year, Best Female Video, and Best Pop Video — for the visual, a tongue-in-cheek comment on fame and the not-so-sparkly side of it. From there, Brit's upswing continued: She released her sixth album, Circus, on November 28, 2008, her fifth to debut atop the Billboard 200, and its lead single, “Womanizer,” was the top single in the country that week, too.

2011: Britney, Video Vanguard Award Winner

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The 28th Annual MTV Video Music Awards - Show

Britney didn't perform at the 2011 VMAs, but it was a significant year for her at the awards show all the same: Britney was named the recipient of the 2011 Michael Jackson Video Vanguard Award for her achievements, and Lady Gaga, in character as Jo Calderone, presented her with the venerable Moonman (and cracked her up in the process). 2011 also marked Britney's return both to the charts and to the stage: She released Femme Fatale, a more club-minded, dance floor–inspired record, and the video for one of its singles, “Till The World Ends,” nabbed her a 2011 VMA for Best Pop Video, too.

2012-2015: Britney Jean, The Small Screen, And The Vegas Scene

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Once touring behind Femme Fatale concluded, Britney tried her hand at two new endeavors: Live TV and Las Vegas. She joined the renowned British talent competition show The X Factor as a judge and coach in 2012; she moved on after one season to focus on her next full-length film and Britney: Piece of Me, her retrospective residency at Planet Hollywood on the Vegas Strip. Though the album didn't match Britney's previous releases as far as chart performance and critical acclaim were concerned, Britney: Piece of Me drummed up so much interest that her career-spanning live show — which was initially scheduled to run through 2015 — was extended through 2017 and given a thorough makeover with a new setlist and aesthetic.

2016: The Glory of Britney

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Britney Spears: Piece of Me Remixed. Reimagined. Still iconic. At Planet Hollywood Hotel & Casino

On August 28, Britney will, once again, hit the VMA stage to turn the page and begin the next chapter of her career. It'll be her first time performing at the VMAs in nearly a decade, and once again, context is key: She's currently the Queen of Las Vegas with Britney: Piece of Me, and she has new music to share thanks to Glory, her new album, which will drop just two days before her performance on August 26.

We've heard a smattering of the new stuff thanks to the singles she's already released, but if Britney's taught us anything about the VMAs, it's that they're unpredictable — and that she's just as big on show-stopping surprises.

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