This study describes the development of album covers throughout history, points out their early start, showcasing the growth of the covers alongside musical genres which were considered popular at time as well as showing their evolution into the format we know today. Different album covers from different genres of music will be analyzed, while their connection with the musical and lyrical content will be closely examined. The practical part of the study will display different albums and album covers from various pop artists, which will then be compared with the author’s redesigns that were aimed to achieve a closer connection to the album’s contents. The author will intend to explain why the original cover was unsuccessful or unoriginal; after offering an original solution, a comparison will be made between the two designs, with the redesign attempting to achieve a greater connection to the album’s content. The goal is to describe the thought process that lead to the redesign as well as point out which of the elements hold the most relevance in the reimagined cover and their role in the overall redesign.