It has been almost 20 years since Guth's original paper fueled considerable excitement in the cosmology community [1]. It was through this paper that many cosmologists saw the first glimmer of hope that certain deep mysteries of the Universe could actually be resolved through the idea of Cosmic Inflation. Today inflation theory has come a long way. While at first the driving forces were deep theoretical questions, now the most exciting developments have come at the hands of new cosmological observations. In the intervening period we have learned a lot about the predictions inflation makes for the state of the Universe today, and new technology is allowing these predictions to be tested to an ever growing degree of precision. The continual confrontation with new observational data has produced a string of striking successes for inflation which have increased our confidence that we are on the right track. Even so, there are key unanswered questions about the foundations of inflation which become ever more compelling in the face of growing observational successes.