Vh1 – Not That Innocent: The Most Shocking Moments When Good Singers Went Bad (And Sexy!)

Britney is listed in second place on the list of “Not That Innocent: The Most Schocking Moments When Good Singer Went Bad” by VH1

2. Britney Spears Does It Again At The 2000 VMAs

We Knew Her When…

Britney Spears had been in the public eye since a young appearance on Star Search in 1991, and most notably in Disney’s The Mickey Mouse Club (along side Ryan Gosling, Justin Timberlake, and even Christina Aguilera). But she became lodged in popular consciousness forever while dancing by her locker in a (slightly altered) Catholic school uniform. 1998?s “…Baby One More Time” sewed the seeds of her legend, but at the time it made her a media darling. She famously announced that she would remain a virgin until marriage, presumably to her old friend and now flame, Justin Timberlake. They even had his ‘n’ hers denim suits made up, y’all!

She weathered her fair share of controversies in 1999 and early 2000s, including a racy Rolling Stone cover and boob job rumors, but it was fairly standard issue for a teen pop star in the spotlight. By May 2000, Britney-Mania had reached a fever pitch with the release of her second album, Oops!…I Did It Again. A change was in the air…
But Then:

Eager and anxious to begin ditching her bubble-gum sound and image, Britney used her appearance at the September 7th awards extravaganza to shake things up. After slinking her way through a cover the Rolling Stone‘s “Satisfaction”, she tore off her MJ-esque suit to reveal a flesh colored body suit that scanned across TV cameras as nude, causing home audience (or at least 12-year-old us) to momentarily wonder if Brit had just ripped her clothes off on national television!

Obviously she definitely didn’t, but it was still a formative TV moment (for us, at least). She seamlessly shifted into “Oops!…I Did It Again,” dancing her heart out like she was born to do. As she purred the final “I’m not that innocent” to close the song, you knew she wasn’t kidding. Many saw it as the begins of her adult career as a more provocative entertainer, and certainly her tabloid headlines got much more salacious soon after. For all of the controversy and personal battles that followed, this performance remains one of her best.
Check the full list here
She deserve 1# spot to be honest.
Credit to Dety