The creation of any work of art often has a purpose or an intent. In this regard, artists endeavour to create pieces of artwork that bear or propagate certain meanings or points of view and also express some social phenomena that are unique to a particular environment or what has often been referred to as a catchment area. This is usually an important artistic undertaking because artists have the innate responsibility to observe certain social peculiarities and visually record them for all their worth. Some of these peculiarities are a reflection of society and its circumstantial behavioural tendencies often brought about by various factors; such as social-economic malaise and bad governance that precipitates social decay. When an artist embarks on such an artistic depiction of his or her own social environment, then there is a need to give it due artistic attention. This study featured 22 paintings based on the subject matter of the overloading of vehicles. Although the paintings appeared generally alike in terms of layout and execution, it is the depiction of the paradox of the repeated occurrence of the same phenomenon which in reality reflects a tendency that is both widespread and bizarre. In this regard, each painting depicts a scene that in reality is in itself a specific curious occurrence. This, in retrospect, can be seen as a type of popular culture of defiance and of the absurd. Since the overloading of any vehicle is ordinarily not only unwarranted and dangerous, but also blatantly illegal, the artist, in his observations which constituted this study, depicts a societal problem that has degenerated into impunity. This study, therefore, sought to find out how effective such focused paintings were as an avenue for social commentary. The artist over a period of time observed incidents of overloading as they manifested themselves in real-life occurrences and made the necessary sketches that were later developed into paintings in the studio. The paintings were examined using formal analysis to delve into their composition and use of elements and principles as well as descriptive analysis to explore their meaning or what the artist intended to convey. The study posits that the essence of such focused paintings in this study is that they become a visual pointer to the wider debate about the debilitating effect of such social malaise upon the psyche of society. The ordinary citizenry subsequently becomes spectators in their own space that degenerates into such recklessness and disregard for individual and collective safety as well as the rule of law