Extant studies of Iranian nationalism accentuate the self-aggrandizing side of Iranian modernity, mainly achieved through, and informing, a process of otherizing certain non-Persians/Iranians, particularly the Arabs. I argue that equally important to understanding Iranian modernity is its lesser recognized, shameful and self-demeaning face, as manifested through a simultaneous 19th-century discourse, which I call “self-deprecating modernity.” This was an often self-ridiculing and shame-inducing, sometimes satirical, discourse featuring an emotion-driven and self-Orientalizing framework that developed out of many mid-nineteenth-century Iranian modernists’ obsessions with Europe's gaze; with self-surveillance; and with the perceived humiliation of Iranians through the ridiculing laughter of Other (especially European) nations at Iran's and Iranians’ expense. To explore this discourse, I re-examine the works of three pre-constitutionalist thinkers and writers within the broader sociopolitical context of late Qajar Iran, surveying their perspectives on shame, embarrassment, and ridiculing laughter, and showing how they were significantly informed by, while also helping to form, self-deprecating modernity. Given the strong, self-colonizing presumptions of this discourse, I conclude the article with a stress on the importance of re-exploring collective self-critical practices in modern Iranian history, culture, and literature with an eye toward decolonizing self-criticism.