As Gadamer, the “dean” of European philosophy, turns 100 this year, it behooves philosophers and reflective people in general to ponder the relation between philosophy and “good life,” and more broadly between philosophy and natural health. As it happens, Gadamer himself has extensively reflected on this issue, especially in a book titled The Enigma of Health. The essay first recapitulates some of the main arguments of Gadamer's text, focusing on the difference between the growing scientific arsenal of medical intervention (combatting illness) and the unforced and un-constructed maintenance of human health through attentiveness to “nature's way.” The middle section inserts the text into the context of Gadamer's larger opus, exploring particularly the connection between health and such key Gadamerian concerns as “appropriateness,” “natural rightness,” and “mimesis.” The conclusion traces affinities between Gadamer and the teachings of Heidegger and Adorno, while also probing the political implications of his text for the maintenance of human freedom in the face of expertocracy and the reduction of politics to ideological blueprints.