The criticism of Hegel's philosophy of history is a recurring theme in the work of the Frankfurt School critical theorists. There is good reason for this, as Hegel's philosophy of history seems to have become hopelessly outdated. After the events of the past two centuries, we can no longer think of the historical process as the manifestation of Reason in the world. Yet there is nonetheless a certain power in the idea of history as spirit working through its inadequacies and self-alienation, a power that authors such as Theodor Adorno and Walter Benjamin do not fully recognize. This dissertation attempts to show how the Hegelian idea of history can be rethought in a way that preserves its critical power, while avoiding the pitfalls of Enlightenment-era historiography. Through the work of Adorno, Benjamin, and Siegfried Kracauer, I try to show that we not only can think of history as a kind of progressive overcoming of an objectivity alien to humanity, but also that such a conception can be beneficial to our projects oriented toward a better present and future.