The present study - Contemporary Images (of the Sublime) - intends to investigate the meaning of the image today. Its main purpose is to develop and broaden the understanding of such concepts as image and sublime in the representative regime of contemporary visuality. From the perspective of this study, the image is not a visual target of an optical framing manifested through projection, under a representational order, or an objective essence previously attributed to the world revealed by the Gaze of a Universal and Sovereign Subject; it is rather an event, the destination of a process related to a game that involves a series of specific mediations named imagerie (production of images). These visual mediations - which are simultaneously technical, semantic and aesthetic - organize the production and the reproduction of subjects within a culture, redefining the concepts of space, time, memory, knowledge and fruition, which implies the end of modern epistemology and the need to create new methods of thinking and, therefore, of visuality. In this context, the double modality of Kant`s concepts of Beauty and Sublime will be considered in the process of founding post-modernity, seen as the present state of the crisis of modern fundaments. The legacy left by the concept of the sublime to aesthetics is related to the recognition of reality as being available for multiple and provisional experiments, bringing reality and art together, making reality as fictional as art itself. The work of the artist Cindy Sherman offers a fertile field for investigation of the notions of image and the sublime. Through the use of photographic technique and support, instead of making objects for art critics, she constitutes herself as an instance of criticism. Sherman builds a metalanguage with which she can then operate with on the mythicogrammatical plane of art. She composes her photographic series with images of displeasure or laughter (rather than pleasure), and the fact that these sensations are presented as substitutes for aesthetic pleasure orients the order of experience in the contemporary scene, which this study intends to investigate.