The severity of our global picture may evoke a common refrain: this is no laughing matter. This dissertation, respectfully, disagrees. In a cultural context mired by the balkanization of information, moral righteousness, and ideological conviction, laughter offers tremendous rhetorical possibilities. This dissertation approaches pessimistic satire from a new vantage point, believing in the ability of pessimism to heal through wounding and persuade through denouncement. Pessimistic satire holds the potential to disentangle ideological commitments in adverse audiences, offering the possibility to reach those who might otherwise be closed off to criticism. I put this possibility to the test through two of the most controversial satiric performances in the Post-Trump Era: Million Dollar Extreme Presents: World Peace and Saturday Night Live’s caricature of Donald Trump by way of Alec Baldwin. These performances show the range of pessimistic satire in the modern era and considering their reception will shed light on the difficulty of complex satire to motivate the proper audience.