This essay examines Nicolas Poussin’s uncharacteristic allegorical painting, A Dance to the Music of Time, in light of its patronage by a Catholic prelate, Giulio Rospigliosi, and as a case study in the nuances of seventeenth-century allegory. Illuminating Poussin’s departures from the popular emblem literature that was his source, and drawing on Walter Benjamin’s rich theorization of baroque allegory in The Origin of German Tragic Drama (which serves as both focus and foil for this reading), the essay argues that the painting uses the obscurity of allegory to more effectively figure spiritual transcendence, and that this transcendence is achieved through, rather than over and against, earthly (and painterly) Pleasure.