On February 19th, 1999, Mike Judge fired “Office Space” into our hearts, minds and frontal lobes and never looked back. At the most recent SAG Awards, Stephen Root, who plays the red-stapler-obsessed Milton, shared with us why he considers #OfficeSpace the “little film that never goes away.” Read writers’ reflections on some of the other biggest pop culture artifacts, milestones and turning points that premiered in 1999, and why understanding 1999 still matters a quarter-century on, in the 1999