The need for American presidential candidates and sitting presidents to connect with citizens has led to the adoption of diverse media strategies that include traditional news initiatives with established journalists, face-to-face interaction with small groups of supporters, and visits to traditionally non-political entertainment-based venues. The American Presidency and Entertainment Media: How Technology Affects Political Communication examines the recent embrace of entertainment forums for political purposes. Featuring interviews with White House insiders and late night talk show veterans, this book analyzes the major moments in the presidency’s increasingly cozy relationship with entertainment-based television shows and the major factors leading individual administrations and campaigns to take chances to reach largely non-political audience. It offers a new theoretical underpinning for this phenomenon, predicts how future campaigns will operate in this regard as media technology and American political culture evolve, and connects the marriage of politics and televised entertainment to the ascension of Donald Trump to the presidency.