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Cities have developed together with the history of humankind throughout the ages. The cities, centre of the social relationships, have experienced a turning point after Industrial Revolution. In the 18th century, the Industrial Revolution was a precursor of a great depression while promising easiness and abundance in production. People started to abandon the countryside and natural life to form population centres in developing sites. The cities, centre of modern life, have not only affected social life, but also the art. The destruction of human life caused by cities has been one of the themes handled by the artists since the Industrial Revolution. Human beings were dragged into consumption culture and anonymization with every passing century. The consumption culture created commoditised people and deep loneliness. The uncontrolled senseless urbanization and anonymization caused by modern life caused desensitisation and introversion among the people. Therefore, the image of city in art carries different meanings. The life of a person in a city has become the pain point rather than the physical appearance of the city. The artists, nowadays, interpret the city through the inner world of the individuals with new forms, manners and technologies. Concordantly, the approach in this thesis titled “City Melancholy” is the melancholy of the individuals created by the changing city perception. In this study, taking into account the relationship between art branches (painting, cinema, literature), individual city experiences take place. The data obtained as a result of literature surveys and readings were used in the thesis. Throughout the study, with the opportunity to observe the city-individual relationship in three different capitals (Vienna, Berlin and Ankara), the individual's inner world with melancholy formed the basis for artistic creation. The experiences gained as an individual living in the city are considered as subjects.