Maturing in the aftermath of Romanticism, Robert Browning wrote memorable poetry that, at its best, provides one basis for understanding the complex relationship between aesthetics and historical consciousness. This chapter attempts to demonstrate how Browning’s Romantic legacies have literary consequences that implicate him in a kind of historicism, which indicates how his aesthetic thought often has great difficulties in containing what extends beyond its powers. The discussion then moves on to examine My Last Duchess, a widely read but highly instructive dramatic monologue that dramatizes the conflict between aesthetics and history in the starkest terms. However, the crucial role of the dramatic monologue in Browning’s development also involves the discussion of two poems, namely, Fra Lippo Lippi and Andrea del Sarto, in the light of the emerging connections between aesthetics and history. These connections offer a path beyond historicism when, to deploy the terminology of Maurice Blanchot, the work that is lost ironically suggests the relations between art and life and provides insight into the situation of the poetic speaker. The conclusion suggests that these two poems can be read as complementary by inviting the reader to imagine a third poem that more clearly invokes Browning’s own ideals.