The article analyzes President Vladimir Putin’s gender-based humor as a way of exploring Russia’s ontological insecurity. Our research explores how Russia’s masculine ontological insecurities are trapped in the realities of patriarchy challenged in a contemporary globalized world. We integrate a constructivist ontology with poststructuralist attention to language to understand the role of gender-based humor in the (re)production of gendered hierarchies, and therefore in sustaining Russia’s ontological security. To achieve our goal, we examined 29 videos of Putin’s speeches broadcast between 2012 and 2022 through the lenses of “feminization” and “masculinization.” The study concludes that it is necessary to take political humor seriously. Its deployment helps Putin to maintain a consistent narrative of Russian self-identity based on associations with masculinity and the feminization of the Russian nation and its foes in the eyes of a conservative segment of the Russian populous. Ultimately, such humor aims to alleviate feelings of insecurity and anxiety, maintaining a heteronormative gendered order in Russian foreign affairs.