While theorizing in distinctly different times, distinctly different cultures, and under distinctly different circumstances, notable philosophical similarities can be drawn between John Dewey and Paulo Freire. This article focuses on two major themes evident in a sample of each philosopher's major works, democracy and experience, and draws theoretical comparisons between the way each philosopher approaches these concepts in terms of definition and application to educational and social practice. The author suggests that, despite some paradigmatic differences, the fundamental definitions and uses of these concepts expressed by both philosophers are largely comparable and complementary.