This article examines the paradoxical relationship between discourses of sincerity and an aesthetics of imperfection in twenty-first-century pop culture, with special attention to the Russian music scene. We focus on the career of cult musician Sergei Shnurov to address this broader question: What do present-day anxieties around sincerity tell us about pop-cultural production and consumption processes? First, we offer a genealogy of post-Soviet sincerity rhetoric. We then use this genealogy to unpack the approach to sincere expression that Shnurov and his critics and fans adopt. Two recurring artistic strategies stand out. First, Shnurov creates a sincere effect by insisting on insincerity. Second, he amplifies this ‘insincerely sincere’ rhetoric by foregrounding a visual aesthetics of imperfection. We argue that these strategies play an important role not only in Shnurov’s biography but also in a broader story: that of sincere expression as a prime concern of twenty-first-century media and popular culture.