Britney Spears: Her Evolution from Pop Princess to Music Icon in Photos

Throughout her nearly 20 years in the spotlight, we've seen Britney in the midst of many different stages of life. Take a look back at the good, the bad – and the unforgettable
By Diana Pearl
Updated August 26, 2016 12:00 PM

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THE MICKEY MOUSE CLUB

Credit: Everett

Born in Mississippi and raised in Kentwood, Louisiana, Spears first came on the scene in 1992 on The Mickey Mouse Club, on which she sang and danced alongside fellow future superstars like Christina Aguilera, Ryan Gosling and Justin Timberlake – her future flame!

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'BABY ONE MORE TIME'

Credit: Courtesy Britney Spears

But it wasn't until the 1998 release of her first big hit, "…Baby One More Time," that Spears shot to serious levels of fame. The song was a huge success for anyone, let alone a first-time artist: It reached No. 1 in every country where it hit the charts, and is still one of the best-selling singles, ever.

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DATING JUSTIN TIMBERLAKE

Credit: Jeffrey Mayer/WireImage

At the time, 'NSYNC ruled the boy band world, just as Spears did the world of female pop stars. So it was just a matter of fate that she'd hook up with 'NSYNC crush bait Justin Timberlake – and that they'd wear matching denim outfits on the red carpet at the 2001 MTV VMAs. It was around this time that her second album, Oops!…I Did It Again dropped, and she did do it again: It was a smash.

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DANCING WITH A SNAKE AT THE VMAS

Credit: Kevin Mazur/WireImage

Good girl Britney, no more! When she strutted her stuff at the 2001 VMAs, wrapped in a snake while dancing to "I'm a Slave 4 U," it was clear that plaid-skirt-and-pigtail-wearing Spears was a thing of the past. She also cemented her status as a VMA legend.

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KISSING MADONNA AT THE VMAS

Credit: Julie Jacobson/AP

Two years later, Spears had another big VMA moment: Her lip lock with Madonna.

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THE 'TOXIC' MUSIC VIDEO

Credit: Source: Britney Spears/YouTube

Another year, another Britney hit. In 2004, that hit was "Toxic," from her album In the Zone, which was, you guessed it, another success. It was herfirst single to reach the Top 10 on the Billboard Hot 100 since "Oops!…I Did It Again."

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MARRIAGE (AND ANNULMENT)

Credit: Kevin Mazur/WireImage

That year was a busy one in her personal life, too. Spears married her childhood friend Jason Alexander in Las Vegas in January, only to annul the marriage after 55 hours. It was that same year that she became engaged to backup dancer Kevin Federline, after just three months of dating. They were engaged for just two more months before marrying in Studio City, California.

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BECOMING A MOM

Credit: Jordan Strauss/Invision/AP

Britney Spears, center, and her sons Sean Federline and Jayden James Federline

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RETURN TO THE CIRCUS

Credit: GSI Media

You can't keep Spears down for long, however. She released her sixth studio album, Circus, in 2008, and it debuted in the No. 1 spot on the charts. The track "Womanizer" gave Spears her first No. 1 single since "…Baby One More Time." Two years later, on the heels of her Circus success, she started dating her agent, Jason Trawick.

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VIVA LAS VEGAS

Credit: Denise Truscello/BSLV/Getty

The true sign of transition from pop star to pop icon? A Las Vegas residency, which began in 2013, just as she was working on her eighth studio album. It was originally supposed to last for two years, but was extended and is still running at Planet Hollywood.

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BRIT BACK ON TOP

Credit: Britney Spears/Instagram

With a ninth (!) album, Glory, and her first VMAs performance in years on the way, it's safe to say Britney's back, bitch. Also, her body is banging. See Instagram for proof.

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THE DOWNWARD SPIRAL

Credit: Chris Wolf/FilmMagic

Spears sought physical and legal custody of her two sons during the divorce, but Federline was given sole legal and physical custody after Spears refused to give up her children when Federline came to pick them up, and was eventually taken to the hospital, with concern that she was under the influence of an unnamed substance. It only got worse from there: She was in and out of rehab facilities, sued by Louis Vuitton, famously shaved her head and was eventually placed under conservatorship of her father Jamie (which she is still under today). However, she still had musical success: Her single "Gimme More" reached Top 10 lists in multiple countries.

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By Diana Pearl