Political caricatures use humor and satire with visual and textual depictions to cast remarks on political figures or situations through exaggerations, disfigurations, or constructed situations. These depictions illustrate or imply the prevailing opinions or consensus on political events or issues. This thesis focuses on Turkey–U.S. relations and representations of the U.S. from 2008 to 2021 in the caricatures on the cover pages of weekly Turkish humor magazines Gırgır, Leman, Penguen, and Uykusuz. The interactions between the U.S. presidents, Barack Obama and Donald Trump, and the Turkish president, Recep Tayyip Erdoğan evolve and change in these exaggerated visual parodies. American symbols and images are used in conjunction with Turkish ones with the aim of providing familiarity and clarifying the meaning in the depicted situations. Absurdity and subversion of events merged with benign familiarity creates political humor and satire. These caricatures claim to present alternative images to understand the covert nuances behind particular political dealings, which classifies them as anti-establishment discourses. The cover pages are analyzed with Greenberg’s (2002) framework and tools to explore the content, method, and messages of caricatures. Affective states of caricaturized subjects and language elements in speech bubbles are included as separate categories. The caricatures and their elements are coded and the results are given in tables and charts to clarify the frequency of appearances. This study utilizes descriptive analysis to characterize various aspects of cover pages and to draw corresponding interpretations by considering the incongruity theory of humor.