This chapter offers a comparison between Gadamer’s hermeneutics and Derrida’s deconstruction, with a focus on their differences. The main difference will be found in their understanding of metaphysics and in the status they give to conceptual philosophical thinking and writing. The chapter will start with a summary of the “unlikely debate” of 1981, followed by Gadamer’s and Derrida’s comments on it and on each other’s work afterwards. In addition, two notions will be discussed, “horizon” and “play”, that can offer a better insight in the diverse approaches of Gadamer and Derrida. Finally, many lines in this chapter will come together in a comparison of Gadamer’s and Derrida’s views on metaphysics and on conceptual thought.