Britney Spears performs at the The Metropolitan Opera House at Lincoln Center in New York City, New York (Photo by Kevin Mazur/WireImage)
KMazur—WireImage
By Cady Lang
August 26, 2016

1999: Britney Spears made her MTV Video Music Awards debut at the show in 1999; fresh off a year of wild success from her breakout album, …Baby One More Time, she performed on the VMAs stage (alongside boy band ‘NSYNC and brief boyfriend Justin Timberlake) for the first time, recreating her title track’s music video, complete with a school-themed set-up and a seductive but sweet stage persona.

2000: The singer proved she was all grown up with a cover of the Rolling Stones’ iconic hit, “Satisfaction,” which she performed in oversized, glitzy menswear — that is, until she ripped off her tuxedo as she strip-teased her way into a performance of her signature song, “Oops…I Did It Again,” clad in a sparkling nude two-piece that showed off her abs.

Also of note: Britney and Christina Aguilera introduced Whitney Houston together. While the singers were civil if wooden together, Aguilera threw some not-so-subtle shade at Eminem during her introduction; the rapper name-checked both singers in his performance of “The Real Slim Shady” that night.

2001: Consider Brit’s 2001 VMA performance one of the most iconic presentations in the history of the franchise. Performing her Pharrell and Chad Hugo-penned track, “I’m a Slave 4 U,” the pop princess gyrated in body oil and little else, most memorably using a python as a dynamic accessory and having a live tiger on the stage.

Another highlight of the night was Spears hanging out the inimitable Mick Jagger on the red carpet, who couldn’t quite remember if Britney had performed his band’s song the year previously at the same ceremony. “Am I a Britney fan?” Jagger queried. “Of course I am. And she did one of our songs, didn’t she? She did it very well.”

Britney Spears and Mick Jagger (Photo by KMazur/WireImage)
KMazur—WireImage

2002: No performance from Britney this year, but the princess of pop was on deck (clad in a black leather dominatrix-esque look) to give the king of pop, one Michael Jackson, a birthday cake. While presenting him with the cake, Brit called him the “artist of the millennium,” which, while probably true, was misunderstood by Jackson, who might have thought it was an award and gave an acceptance speech unrelated to the cake.

Britney Spears and Michael Jackson on stage at the 2002 MTV Video Music Awards at Radio City Music Hall in New York City, August 29, 2002. Photo by Scott Gries/ImageDirect.
Scott Gries—Getty Images

2003: What do you get when you put two pop songstresses on the stage with a woman who trailblazed the way for the both of them? The most outrageous performance in VMA History, according to the public. The Queen of Pop joined Britney and Christina Aguilera for a rendition of her “Like A Virgin” not soon to be forgotten; during the performance, Madge and the girls bumped, grinded, and then lip locked until Missy Elliott came out to join them on stage. The reactions ranged from a very unhappy Justin Timberlake to a very bemused Paris Hilton, which is to say that this is a moment that truly defined the early-aughts and should probably be commemorated forever.

2004 – 2006: Alas, Britney did not attend the VMAs during this time, thus depriving us of any truly spectacular moment to remember; however, in lieu of dancing with a banana snake or kissing Madonna, Brit did however, hook up with her backup dancer/aspiring rapper K-Fed (otherwise known as Kevin Federline), with whom she had two children. For the 2006 awards, she and K-Fed appeared via satellite to introduce the award for Best R&B video; the appearance featured the couple poking fun at themselves and Britney pregnant with their second child.

2007: Britney’s return to the VMA stage was less than victorious; as audiences found the performance of “Gimme More” to be tepid, rushed and lip-synched.

2008: The unprepared Spears of the year before was nowhere to be found when Britney took the stage in 2008 to accept her very first Moonman award. The singer didn’t perform, but looked happy and healthy as she took home three awards, all for “Piece of Me.”

Britney Spears accepts the Best Female Video award for "Piece of Me" on stage at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)
Kevin Winter—Getty Images

2009: Britney couldn’t make it to the awards show because she was on her The Circus Starring Britney Spears tour, but she did check in via satellite with the viewers at home to thank them for awarding “Womanizer,” the Best Pop Video.

2010: No Britney at the VMAs in 2010.

2011: Britney returns to the VMAs in 2011, where she is presented with the Michael Jackson Video Vanguard Award, which included a VMA tribute. She took home Best Pop Video that year, and in traditional Brit fashion, shared a buzzy kiss with Lady Gaga’s alter-ego Jo Calderone.

2012 — 2014: If Britney Spears doesn’t go to the MTV VMAs, did they even happen? That’s the way we feel about these lost years. Brit wasn’t entirely forgotten, however — singer Katy Perry paid homage to Brit and Justin’s iconic Canadian tuxedo red carpet look from the American Music Awards at the 2014 VMAs, which earned a thumbs up from Spears.

2015: Brit returned to the VMAs as the first presenter, handing out Best Male Video Award, which ended up going to Mark Ronson and Bruno Mars for “Uptown Funk.”

Britney Spears speaks onstage during the 2015 MTV Video Music Awards at [f500link]Microsoft[/f500link] Theater on August 30, 2015 in Los Angeles, California. (Photo by Kevork Djansezian/Getty Images)
Kevork Djansezian—Getty Images

2016: Britney’s back and better than ever and she’s counting on this year’s VMAs to be the launch of a “new era.” Nearly 17 years after she first took the stage, Spears will be giving her first live performance for the VMAs since 2007’s notorious offering. Fresh off the drop of her latest album, Glory, she’ll be performing the lead single, “Make Me,” alongside Bay Area rapper G-Eazy.

Write to Cady Lang at cady.lang@timemagazine.com.

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