Social studies teachers are tasked with aiding their students' abilities to engage in public debate and make politically sound decisions. One way the authors have found to help facilitate this is to draw connections between content knowledge and current political conversations through the use of clips from "The Daily Show with Jon Stewart." While acknowledging that "The Daily Show" may be perceived as reflecting a particular ideological orientation, Stewart has insisted that any politician or issue is fair game for comedic/critical treatment on his program; indeed, within "The Daily Show" online archive, there are numerous clips of monologues with pointed critiques of both left and right. In the activities in this article, the authors describe how "The Daily Show" can be used to both highlight the relevance of content knowledge and to model a media critique that transcends a specific political orientation, providing students with a set of practices they can bring to the viewing of any news media presentation. (Contains 2 figures and 7 notes.)