This Festschrift contains numerous colorful and eclectic essays from well-known mathematicians, philosophers, logicians, and linguists celebrating the 90th birthday of Reuben Hersh. The essays offer, in part, attempts to answer the following questions set forth by Reuben himself as a focus for this volume: Can practicing mathematicians, as such, contribute anything to the philosophy of math? Can or should philosophers of math, as such, say anything to practicing mathematicians? Twenty or fifty years from now, what will be similar, and what will, or could, or should be altogether different: About the philosophy of math? About math education? About math research institutions? About data processing and scientific computing? The essays also offer glimpses into Reuben’s fertile mind and his lasting influence on the mathematical community, as well as revealing the diverse roots, obstacles and philosophical dispositions that characterize the working lives of mathematicians. With contributions from a veritable “who’s who” list of 20th century luminaries from mathematics and philosophy, as well as from Reuben himself, this volume will appeal to a wide variety of readers from curious undergraduates to prominent mathematicians.