Popsugar Celebrity The '90S Britney Spears Pictures From 1999 20 Years Later, Look Back at Britney Spears's First Year as a Pop Icon 11 January 2019 by Laura Marie Meyers View On One Page Photo 14 of 20 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 14 September 1999 Speaking of the MTV VMAs, here's the *look* Miss Spears rocked that night. Previous Next Start Slideshow The '90sNostalgiaBritney Spears