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Britney Spears
Britney Spears decked herself out in a leather bondage outfit for 2002, but apparently forgot to bring her whip
Don Emmert/ Getty Images
Britney Spears
Britney Spears proved she was savvy enough to poke fun at both herself and the public's perception of her, with her high-profile cameo on "The Late Show With David Letterman"
CBS
Britney Spears
Britney Spears seemed to have found love with boyfriend/manager Jason Trawick, and was spotted vacationing with him in Australia in November
Oceanic Media Group/FilmMagic
Britney Spears
Britney Spears kicked off her big-budget
Circus
tour in March, with a triumphant show in her (sorta) hometown of New Orleans
Kevin Mazur/WireImage
Britney Spears
Britney Spears' sultry single "If U Seek Amy," with its censor-tweaking chorus, was a smash hit and helped Brit make her comeback
Jive
Britney Spears
Britney Spears' "3," the lone new track off
The Singles Collection
, made
Billboard
Hot 100 history when it debuted at #1 on the chart
Jive
Britney Spears
Britney Spears accepts the Best Pop Video award for 'Womanizer' at the 2009 MTV Video Music Awards.
Britney Spears
Britney Spears accepts the Best Pop Video award for 'Womanizer' at the 2009 MTV Video Music Awards.
Britney Spears
Britney Spears accepts the Best Pop Video award for 'Womanizer' at the 2009 MTV Video Music Awards.
Britney Spears
Britney Spears displays her awards after the 2008 VMAs
Jon Kopaloff/Getty Images
Britney Spears
Much like the crowded streets of Times Square, Britney Spears is constantly surrounded by flocks of fans and flashing camera lights. When people think of NYC, they think of Times Square. When people think of the VMAs, they think of Britney Spears.
Getty Images/ MTV News
Britney Spears
Multiple Moonman winner Britney Spears looks ready to add juggling to her singing, dancing repertoire at the 2008 MTV Video Music Awards.
Getty Images
Britney Spears
Britney Spears pushes the envelope at the 2001 VMAs in a lacey ensemble. Mexican pop singer Paulina Rubio takes it up a notch in 2005 with a longer, barely-there version.
Getty Images
Britney Spears
Renee Zellweger brings crimped hair back from the '80s at the 1999 VMAs and Britney brings it to the new millenium in 2000.
Getty Images
Britney Spears
Russell Brand and Britney Spears commandeer a golf cart to ride over to see Kanye West in the last VMA performance of the night.
MTV
Britney Spears
Russell Brand talks to Britney Spears while ignoring the elephant in the room.
MTV
Britney Spears
Russell Brand poses with a very cheerful Britney Spears and a very naked elephant.
MTV
Britney Spears
What's Russell Brand doing to Britney Spears' finger? Regardless, he's cracking her up.
MTV
Britney Spears
An elephant helps Russell Brand and Britney Spears promote the 2008 MTV VMAs.
MTV
Britney Spears
09.09.07, Las Vegas, NV: Somehow we don't think Britney Spears was talking about clothes as she strutted around the stage singing 'Gimme More' in this lingerie inspired outfit.
MTV
Britney Spears
09.06.2001, New York City, NY: Hello curves! Britney Spears wears an entirely see-through lace mini-dress at the 2001 VMAs.
MTV
Britney Spears
Britney Spears at London Zoo on June 16, 2009 in London, England.
Sam Snap/FilmMagic
Britney Spears
Britney Spears had a big 2008, highlighted by her big VMA wins on September 7.
Steve Granitz/WireImage
Britney Spears
Britney Spears performs at the Bambi Awards 2008 Show on November 27, 2008 in Offenburg, Germany.
Sascha Baumann/WireImage
Britney Spears
Singer Britney Spears poses with the Best Female Video Award, Best Pop Award and Video of the Year Award for "Piece of Me" in the press room at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California.
Dave Hogan/Getty Images
Britney Spears
Britney Spears speaks on stage during the pretaping of 76th Rockefeller Center Christmas tree lighting ceremony at Rockefeller Center on December 2, 2008 in New York City.
Frank Micelotta/Getty Images
Britney Spears
Britney Spears performs on ABC's "Good Morning America" at The Big Apple Circus Tent at Lincoln Center on December 2, 2008 in New York City.
Kevin Mazur/WireImage
Britney Spears
Singer Britney Spears appears onstage to perform with Madonna during her Sticky and Sweet Tour at Dodger Stadium on November 6, 2008 in Los Angeles, California.
Kevin Winter/Getty Images
Britney Spears
Britney Spears performs on ABC's "Good Morning America" at The Big Apple Circus Tent at Lincoln Center on December 2, 2008 in New York City.
Kevin Mazur/WireImage
Britney Spears
Britney Spears leaves Bally Fitness on May 7, 2008 in Culver City, California.
Jean Baptiste Lacroix/WireImage
Britney Spears
Singer Britney Spears speaks on stage at the 'Light of the Angels' Holiday Tree Lighting Ceremony at LA Live on December 4, 2008 in Los Angeles, California.
Jeff Kravitz/FilmMagic
Britney Spears
Britney Spears performs on ABC's "Good Morning America" at The Big Apple Circus Tent at Lincoln Center on December 2, 2008 in New York City.
Kevin Mazur/WireImage
Britney Spears
TV Personality Paris Hilton and Singer Britney Spears at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California.
Chris Polk/FilmMagic
Britney Spears
Britney Spears poses backstage at The Hit Musical "In The Heights" on Broadway at The Richard Rogers Theater on September 30, 2008 in New York City.
Bruce Glikas/FilmMagic
Britney Spears
Britney Spears, winner in the category pop international, poses with the trophy at the Bambi Awards 2008 on November 27, 2008 in Offenburg, Germany.
Florian Seefried/Getty Images
Britney Spears
Britney Spears is seen at Rockefeller Center during the Christmas tree lighting on December 2, 2008 in New York City.
Arnaldo Magnani/Getty Images
Britney Spears
Singer Britney Spears on stage at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California.
Jason Merritt/FilmMagic
Britney Spears
Singer Britney Spears performs on ABC's "Good Morning America" at The Big Apple Circus tent at Lincoln Center on December 2, 2008 in New York City.
Bryan Bedder/Getty Images
Britney Spears
Britney Spears sighting at the Nokia Theater on December 4, 2008 in Los Angeles, California.
Jean Baptiste Lacroix/WireImage
Britney Spears
#2. Britney Spears
Getty Images
Britney Spears
Singer Britney Spears performs on ABC's "Good Morning America" at The Big Apple Circus tent at Lincoln Center on December 2, 2008 in New York City.
Frank Micelotta/Getty Images
Britney Spears
Singer Britney Spears performs during the Bambi Awards 2008 Show on November 27, 2008 in Offenburg, Germany.
Andreas Rentz/Getty Images
Britney Spears
Britney Spears
Zomba
Britney Spears
Britney Spears
Zomba
Britney Spears
Singer Madonna, with special guest singer Britney Spears, performs during her Sticky and Sweet Tour at Dodger Stadium on November 6, 2008 in Los Angeles, California.
Kevin Winter/Getty Images
Britney Spears
Singers Jordin Sparks and Britney Spears at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California.
Kevin Mazur/WireImage
Britney Spears
Her name is Britney Spears. You may have heard of her. Here she foreshadows her three VMA victories with a silvery shimmer that matches the Moonman's.
Getty Images
Britney Spears
Britney Spears and her moonman for Best Female Video, Best Pop Video and Video Of The Year.
Getty Images
Britney Spears
After going her whole career without a VMA win, Britney proudly shows of the three Moonmen she won in a single night for 'Piece Of Me.'
Getty Images
Britney Spears
Spears proudly makes her way out of the Press Room of the 2008 MTV VMAs.
WireImage
