This article describes and reflects upon efforts to generate greater support for media literacy and critical thinking within the strategies and programs of the Federal government in the early 1990s to about 2005 primarily among agencies with an interest in youth substance abuse prevention. Beginning with their personal reflections on discovering media literacy, the authors describe the wide range of initiatives that occurred under their leadership in bringing media literacy into the 1996 National Drug Control Strategy. Additionally, some of the inherent challenges and obstacles that impacted the ability to expand these efforts are described. The authors each served as Associate Director of the White House Drug Policy Office and Director of the National Youth Anti-Drug Media Campaign.