The main objective of this paper is to analyse two national paintings. Those paintings were pioneers in treating about female sex trade. They are an example about the complicated relationship between Fine Arts and the world of prostitution in Chile during the first half of the 20th century. It is argued that the tension between Fine Arts and representation about marginality as a result of urban modernization, represent an unresolved conflict at that time, because in Chile the paradigm of "beauty" was linked with the conservative and neoclassical European model. For this reason, the themes of suburb were expulsed to the edges of Academy. In this paper, we express, how artists who dared to deal with the subject of prostitution, were rejected or ignored. That made them change the theme of their artwork or receive posthumous recognition.