Abstract My point of departure is the idea that Wittgenstein's work, especially his later work with its explicit emphasis on practices, seeks to engage a reader who is likely to come to philosophy with a certain cast of mind that includes unexamined commitments from a particular cultural context. I show how a substantial number of remarks by Wittgenstein in which he addresses cultural topics bring out the importance of the quite specific connections he saw between the philosophical problems with which he grappled and the historical cultural context in which those problems have arisen. Not only is a grasp of this aspect of his writing integral to a proper understanding of Wittgenstein as a thinker, bringing out these connections serves to put these remarks into a coherent conceptual framework. In assessing the relation of Wittgenstein's cultural concerns to his engagement with metaphysics, I show how his development of Spengler's thought is an important connecting link. Particularly important for this analysis will be my discussion of Wittgenstein's understanding and employment of the concept of a Betrachtungsform, as well as a few closely related concepts. I then offer an interpretation of what I believe to be the significance of the connection in his later thought between his philosophical activity and his views about the modern West.