For a long period of time, artistic work has served as a tool to convey different messages and even intimate feelings among individuals. However, artists are not confined to message conveyance only since many even utilize the avenue as a hobby. In the history of arts, the works of Pablo Picasso and Vincent Van Gogh have won admiration across many quarters. The paper explores comparisons between the portrait of Gertrude Stein developed by Pablo and that of Madame Joseph-Michel Ginoux, a brainchild of Van Gogh.