Recent reports on the media saturation experienced by the twenty-first century student have brought about an increased interest in focusing attention on the issue of visual literacy in today's schools. Concepts such as instructional personalization, where approaches to curriculum design and instruction are created to concentrate on the individual strengths of the learner, have been promoted by some as a path to improving overall student performance. Many believe that the content of the Social Studies classroom easily lends itself to a visually stimulating approach and as such is an ideal laboratory to test hypotheses on such an approach. This study examines the use of one such visual tool in the Social Studies content arena, the political cartoon. Political cartoons are believed to be ideally suited to appeal to the visually oriented characteristics of the millennial student in the form of a potentially content rich primary source document. Described within the pages of this paper are the unique experiences with using political cartoons from the perspective of both middle school American History students and their teacher. The qualitative data uncovered through the collection of these experiences clearly illustrates a noticeable disparity between teacher and student experiences with cartoons from the present and their counterparts from the past. While present day cartoons covering various recent events in the news elicited an impressive level of informational recall and personal connections to the topics covered, the results were considerably less spectacular when political cartoons from the distant past were utilized. Those older images were more difficult for the students to grasp the artist's intent and failed as an opportunity for the students to demonstrate their mastery of content knowledge. It was concluded through an examination of interviews from both teacher and student that the differences observed between the older and newer images may be a function of several factors. Chief among these possible explanations from the point of view of the student was the lifelong collection of experiences that each child brought with them to the process of analyzing a political cartoon. The unique cultural capital possessed by each student as a result of their daily, almost nonstop exposure to all forms of media created a personal connection to the modern material that could not be matched by the content from the past. It was also revealed to be possible that a portion of the blame for the difficulties experienced with the materials from the past could be the result of the day to day decisions made by this one particular classroom teacher. The time and dedication to the mastery of the content knowledge and procedural skills necessary to decipher political cartoons from the past may have been insufficient to the task at hand. Conclusions drawn from the information collected in these interviews focus on decreasing the discrepancy between the two forms of visual material by taking steps that include considerable work on the part of the teacher and student to improve upon the background content knowledge and processing skills necessary to consistently decipher the information contained within the political cartoons. Such steps may prove to be impractical given the nature of the already jam-packed curriculums and time-strapped teachers that populate today's Social Studies classrooms. Additional studies would be necessary to determine if the experiences viewed here are common to those encountered in other parts of the nation or if they are indeed uniquely characteristic of this one situation. Accordingly, the results of those additional studies would possibly initiate a reevaluation of the conclusions drawn here.