Should philosophers, on occasion, be embarrassed in their work? Were they? We look at some cases in the history of modern philosophy and study the grounds for embarrassment and the way philosophers have dealt with it. Hume and Wittgenstein are our prime examples of philosophers who were aware that through their work, they had undermined the very possibility of doing such work—that the aims of traditional philosophy are out of reach—and thus have been thoroughly embarrassed. What are the upshots, they ask, for philosophers and their subject? One way of responding was to give up the traditional aims so as to protect oneself from further embarrassment. This was the strategy we find in the early Wittgenstein, the Vienna Circle, and in Quine who, in their own ways, tried to reconceive the aims and subject matter of philosophy in a narrow fashion that took science as its model. This move, however, comes with its own embarrassments, as we illustrate with the later Wittgenstein’s cautionary remarks about the embarrassments of scientism and his warnings about the related inclination to self-deception.