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 4 of 20 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 4 May 1999 She sat down with Regis Philbin and Kathie Lee Gifford for an episode of their show taped at Disney World in May. Previous Next Start Slideshow The '90sNostalgiaBritney Spears