Videography: Britney Spears

It’s Britney, bitch. The lady Spears shimmied along in 1998, following in the syncopated dancesteps of Janet and Madonna to become a pop culture icon in her own right. Like those enterprising queens, Brit employed a series of reinventions throughout her career and suffered a few bumps along the way, but she’s back and still churning out the hits nearly 15 years later. Let’s take a tour of Britney Spears’ greatest — and most questionable — video looks. 

“…Baby One More Time” (1998)

And a star is born. Is there a more indelible image from the late-90s than a then-16-year-old Spears dressed as a schoolgirl, dancing around in a pigtails and knee-high socks? That video and its iconic costume set the tone for the first few years of her career, blending innocence with a subversive and at times unsettling sexuality.