Reactionary critics of modernity often accuse liberal societies of producing the wrong kind of person. For some, Liberal Man is too weak, too cowardly, and too mediocre. For others, Liberal Man neglects his family, his country, and his God. The narratives vary, but the charge remains the same: beneath the smiling face of pluralism hides a desire to exterminate the great, the good, and the beautiful. In this chapter, I focus on two thinkers who share the view that “illiberal lives” are preferable to “liberal lives,” but nonetheless believe that liberal societies are worth defending: Isaiah Berlin and Michael Oakeshott. Drawing on their work, I argue that Berlin and Oakeshott defend two counter-intuitive theses: that liberal societies thrive when their citizens lead “illiberal lives,” and that “illiberal lives” are best led in liberal societies.