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A Roundup of Britney Spears’ Best and Worst VMA Looks of All Time: Pics

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Britney Spears has had some seriously memorable moments at the MTV Video Music Awards. From kissing Madonna to performing “I’m a Slave 4 U” with a live boa constrictor around her neck, the singer has owned the annual awards show many a time.

Naturally, each of these crazy situations featured an equally wild ensemble. So as we prepare for the 2020 VMAs, we’re taking a look back at some of the “Toxic” songstress’ wildest and best looks of all time.The singer attended the awards show for the first time in 1999.

The then 18-year-old had three different looks over the course of the evening, all of which were a touch risqué but nothing like what she ultimately debuted in later years.

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