To see comicality in the reach of imperialism is to see the rhetorical force of empire itself in collective imaginations. This article approaches matters of empire through the lens of caricature. More specifically, it frames caricature as a rhetorical counterforce to images and ideas of imperialism. Comics publication the Nib put out an “Empire” issue in 2019. In an effort to figure out how a comic stretch of the imagination represents empire across histories, geographic locations, and cultural milieus for what it is—a mechanism of disimagination—I explore several standout comics and editorial cartoons in the issue. Looking at themes of monumentality and the taint of collective memory, historical revisionism and historiographical ridicule, and cultural dominion, I argue that caricature in the Nib's “Empire” issue reimagines imperialism, comically, as a complex (even if reductive) way of organizing a lack of imagination.