Focusing on Norman Rockwell’s “Four Freedoms,” this essay argues the idea that due to the inevitable passage of time and lack of direct experience with an event or era, our views and opinions as a 21st century audience regarding the “Four Freedoms,” and images in general, differ from those of the original intended audience. I extend Kimble and Olson’s idea of exposing so-called ‘truths’ in exchange for actual contextual reality, only instead of applying that to J. Howard Miller’s “We Can Do It!” and Norman Rockwell’s “Rosie the Riveter” like Kimble and Olson did, I apply it to Rockwell’s “Four Freedoms” and I take the extra step by focusing on the general public’s reactions today versus those of the American public in the 1940s. In terms of sources, I use Kimble and Olson’s idea as explained above, as well as Hennessey and Knutson’s, Herbst’s, Olson’s, and Westbrook’s prior analysis of the images along with a transcript of President Franklin Roosevelt’s 1941 State of the Union address, which inspired Rockwell to create the images in the first place, to complement my own formal analysis and contextual study. I utilize Erwin Panofsky’s systematic three-layer method with the natural, conventional, and intrinsic meaning levels only at a smaller scale due to the number of images, and Peter Burke’s “cohesive method,” as used in Kimble and Olson’s article, in order to study each individual image as a part of a whole. Lastly, I implement a short survey of 20 George Washington University freshman students to record first impression thoughts in order to gain some insight into how we, as a 21st century educated society, view the “Four Freedoms.” I use those findings to compare and contrast original intentions and views and current beliefs and views. The survey results, although very small in number, indeed shed some light on the question of disparity between audiences. In the end, I recount the actual stories behind the four images’ creation, intention, reception, and evolution into what we view them as today. Without completely disclosing specific findings, it seems as if we, as a 21st century audience, can not fully understand the images, due to the lack of emotional analysis and connection resulting from the passage of time and generational and era differences, but we seem to at least be able to appreciate the works as historical relics of our American history. To us the “Four Freedoms” are visual artifacts, but during the 1940s Rockwell provided both a moment of escape through the celebration of life’s little moments and a reason to fight, to hope, and to dream.