The Spanish-American philosopher, George Santayana, is not easily classified. Viewing him as a classical American philosopher may not do justice to his thought. His philosophy has strong ties with Arthur Schopenhauer’s, yet he does not properly belong to any school of thought presented in this Handbook. His complex account of the comic and the tragic and the central role that laughter, humor, additional cognates of the comical, and cheerfulness play in his original thought deserve a thorough presentation.